Robert M. Silverstein, Francis X. Webster, David Kiemle-Solutions Manual for Spectrometric Identification of Organic Compounds-Wiley (2005)
April 5, 2017 | Author: David Santiago | Category: N/A
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Answers for Student Exercises 1.1 to 1.5
1
a 3-ethyloctane C10H22
CnHmXxNyOz Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
IHD 0
Atom Type Hydrogen Carbon Nitrogen Oxygen Sulfur Bromine
# of Atoms Mass 1.00783 22 10 12.00000 14.0031 0 15.9949 0 31.9721 0 78.9183 0 Exact Mass
Total Mass 22.17226 120.00000 0.00000 0.00000 0.00000 0.00000 142.17226
- (C2H5 ) Rule 3
- (C5H11 ) Rule 3 H
- (CH2=CH2) Rule 9
b
3-butylcyclohex-1-ene C10H18 CnHmXxNyOz Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
IHD 2
Atom Type Hydrogen Carbon Nitrogen Oxygen Sulfur Bromine
or
- (C4H9 ) Rule 5 and 6
- (CH2=CH2) Rule 6
- (C3H7 ) Rule 3
# of Atoms Mass 1.00783 18 10 12.00000 14.0031 0 15.9949 0 31.9721 0 78.9183 0 Exact Mass
Total Mass 18.14094 120.00000 0.00000 0.00000 0.00000 0.00000 138.14094
Answers for Student Exercises 1.1 to 1.5
2 Atom Type Hydrogen Carbon Nitrogen Oxygen Sulfur Bromine
O c
2-methyl-1-phenylhexan-1-one C13H18O
CnHmXxNyOz Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
IHD 5
# of Atoms Mass 1.00783 18 13 12.00000 14.0031 0 15.9949 1 31.9721 0 78.9183 0 Exact Mass
O
O
Total Mass 18.14094 156.00000 0.00000 15.99490 0.00000 0.00000 190.13584
O
- (C6H13 ) Rule 8 O
O
- (C6H5 ) Rule 8
O
H
O
- (C4H8)
OH H
Rule 9 O - (CO) Rule 8+9 Atom Type Hydrogen Carbon Nitrogen Oxygen Sulfur Bromine
d (E)-undec-3-ene C11H22
CnHmXxNyOz Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
IHD 1
or
- (CH3) Rule 5 - (C6H13) Rule 5 H
- (C7H14) Rule 9
# of Atoms Mass 1.00783 22 11 12.00000 14.0031 0 15.9949 0 31.9721 0 78.9183 0 Exact Mass
Total Mass 22.17226 132.00000 0.00000 0.00000 0.00000 0.00000 154.17226
Answers for Student Exercises 1.1 to 1.5 e
1-(hexan-2-yl)benzene C12H18
CnHmXxNyOz Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
IHD 4
3 Atom Type Hydrogen Carbon Nitrogen Oxygen Sulfur Bromine
# of Atoms Mass 1.00783 18 12 12.00000 14.0031 0 15.9949 0 31.9721 0 78.9183 0 Exact Mass
Total Mass 18.14094 144.00000 0.00000 0.00000 0.00000 0.00000 162.14094
- (CH3 ) Rule 7
- (C4H9 ) Rule 7 - (C4H8 )
H
H
Rule 9 H f
OH heptan-2-ol C7H16O
CnHmXxNyOz Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
OH
OH
H OH
H OH
IHD 0
Atom Type Hydrogen Carbon Nitrogen Oxygen Sulfur Bromine
# of Atoms Mass 1.00783 16 7 12.00000 14.0031 0 15.9949 1 31.9721 0 78.9183 0 Exact Mass
Total Mass 16.12528 84.00000 0.00000 15.99490 0.00000 0.00000 116.12018
- (C5H11 ) Rule 8
OH
- (CH3 ) Rule 8
OH
- (H ) Rule 8 - (H2O) Rule 9
OH
Answers for Student Exercises 1.1 to 1.5
g
COOH 3,5,7-trimethyloctanoic acid C11H22O2
CnHmXxNyOz
IHD 1
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
4 Atom Type Hydrogen Carbon Nitrogen Oxygen Sulfur Bromine
# of Atoms Mass 1.00783 22 11 12.00000 14.0031 0 15.9949 2 31.9721 0 78.9183 0 Exact Mass
Total Mass 22.17226 132.00000 0.00000 31.98980 0.00000 0.00000 186.16206
O C O
- (OH ) OH
Rule 8
O C
O OH
H
O
O
- (C10H21 )
C
Rule 8
O
- (C9H18) Rule 9
HO h
OH hexan-1-ol C6H14O
CnHmXxNyOz Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
IHD 0
Atom Type Hydrogen Carbon Nitrogen Oxygen Sulfur Bromine
O C
OH H
OH
OH
HO
HO
# of Atoms Mass 1.00783 14 6 12.00000 14.0031 0 15.9949 1 31.9721 0 78.9183 0 Exact Mass
Total Mass 14.10962 72.00000 0.00000 15.99490 0.00000 0.00000 102.10452
H H
O
- (CH2=CH2 ) - (H2O) Rule 9
OH
- (C5H11 ) Rule 8
H 2C
OH
- (H ) OH
Rule 8
OH
Answers for Student Exercises 1.1 to 1.5
i
OH 2-methylheptan-2-ol C8H18O CnHmXxNyOz
IHD 0
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
5 Atom Type Hydrogen Carbon Nitrogen Oxygen Sulfur Bromine
# of Atoms Mass 1.00783 18 8 12.00000 14.0031 0 15.9949 1 31.9721 0 78.9183 0 Exact Mass
Total Mass 18.14094 96.00000 0.00000 15.99490 0.00000 0.00000 130.13584
- (C5H11 )
OH
OH
Rule 8 - (CH3 )
OH
OH
Rule 8
H H
O
- (H2O)
- (CH2=C(CH3)2)
Rule 8
Rule 8
j
S butyl(propyl)sulfane C7H16S
CnHmXxNyOz Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
S
IHD 0
Atom Type Hydrogen Carbon Nitrogen Oxygen Sulfur Bromine
# of Atoms Mass 1.00783 16 7 12.00000 14.0031 0 15.9949 0 31.9721 1 78.9183 0 Exact Mass
- (C3H7 ) Rule 8
- (CH2=CH2)
S
Rule 9
H
S
Total Mass 16.12528 84.00000 0.00000 0.00000 31.97210 0.00000 132.09738
- (C2H5 ) Rule 8
S
SH
S
Answers for Student Exercises 1.1 to 1.5 k
OH (2-hexylphenyl)methanol C13H20O CnHmXxNyOz
IHD 4
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
OH
6 Atom Type Hydrogen Carbon Nitrogen Oxygen Sulfur Bromine
# of Atoms Mass 1.00783 20 13 12.00000 14.0031 0 15.9949 1 31.9721 0 78.9183 0 Exact Mass
OH
or
- (C5H11 )
OH
OH
Rule 7
CH2 CH2
- (OH )
OH
Total Mass 20.15660 156.00000 0.00000 15.99490 0.00000 0.00000 192.15150
Rule 7 OH
- (H2O)
H
Rule 9
O l
NO2 (4-nitrophenyl)(phenyl)methanone C13H9NO3
CnHmXxNyOz
IHD 10
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
Atom Type Hydrogen Carbon Nitrogen Oxygen Sulfur Bromine
# of Atoms Mass 1.00783 9 13 12.00000 14.0031 1 15.9949 3 31.9721 0 78.9183 0 Exact Mass
Total Mass 9.07047 156.00000 14.00310 47.98470 0.00000 0.00000 227.05827
O
O - (C6H4NO2 ) NO2 O
Rule 7&8 - (CO) Rule 8&9 O
O - (C6H5 ) NO2
Rule 7&8
NO2
Answers for Student Exercises 1.1 to 1.5
m
O
3-(ethoxymethyl)heptane C10H22O
CnHmXxNyOz
IHD 0
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
7 Atom Type Hydrogen Carbon Nitrogen Oxygen Sulfur Bromine
# of Atoms Mass 1.00783 22 10 12.00000 14.0031 0 15.9949 1 31.9721 0 78.9183 0 Exact Mass
- (CH3 )
O
O CH2
Rule 8
- (C7H15 )
O
Total Mass 22.17226 120.00000 0.00000 15.99490 0.00000 0.00000 158.16716
O
Rule 8
- (C4H9)
O
O
Rule 3
O n
H Br 2-bromodecanal C10H19BrO
CnHmXxNyOz
IHD 1
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
O
Atom Type Hydrogen Carbon Nitrogen Oxygen Sulfur Bromine
# of Atoms Mass 1.00783 19 10 12.00000 14.0031 0 15.9949 1 31.9721 0 78.9183 1 Exact Mass
Total Mass 19.14877 120.00000 0.00000 15.99490 0.00000 78.91830 234.06197
O
- (H ) H
Br
Rule 8
Br
O - (CO ) Rule 9
Br
Br H
H O H Br
- (C8H16) Rule 9
O H
H Br
Answers for Student Exercises 1.1 to 1.5 o
O O cyclohexyl acetate C8H14O2 CnHmXxNyOz
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
O
O
IHD 2
8 Atom Type Hydrogen Carbon Nitrogen Oxygen Sulfur Bromine
- (C6H11O )
# of Atoms Mass 1.00783 14 8 12.00000 14.0031 0 15.9949 2 31.9721 0 78.9183 0 Exact Mass
Total Mass 14.10962 96.00000 0.00000 31.98980 0.00000 0.00000 142.09942
O
Rule 8
O
O
- (CH3 )
O
O
Rule 8
O H
O
- (CH2=C=O) Rule 9
O
H
Answers for Student Exercises 1.6 to 1.11 A
O
9
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
71
114
99 / C6H11O
15 / CH3
86 / C5H10
28 / C2H4
71 / C4H7O
43 / C3H7
58 / C3H5O
56 / C4H8
43 / C3H7
71 / C4H7O
4-Heptanone C7H14O Exact Mass: 114.1045 IHD = 1, match with (k)
B
OH
4-Bromotoluene C7H7Br Exact Mass: 169.9731 IHD = 4, match with (v)
D
Fragement Ion
Fragment Loss
59
116 by CI
115 / C7H15O
1/H
98 / C7H14
18 / H2O
87 / C5H11O
29 / C2H5
69 / C5H9
18 / H2O, 29 / C2H5
59 / C3H7O
57 / C4H9
45 / C2H5O
71 / C5H11
43 / C3H7
73 / C4H9O
41 / C4H5
18 / H2O, 57 / C4H9
R
Rearrangment R R
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
91
170
91 / C7H7
79 / Br
Rearrangment Tropylium Ion
75 / C6H3
80 / HBr, 16 / CH4
R
65 / C5H5
79 / Br, 26 / C2H2
R
50 / C4H2
120 / C7H5Br
39 / C3H2
131 / C4H5Br
Br
2-Bromopentane C5H11Br Exact Mass: 150.0044 IHD = 0, match with (r)
R
Molecular Ion
C7H16O Exact Mass: 116.1201 IHD = 0, match with (m)
Br
R
Base Peak
3-Heptanol
C
Rearrangment
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
71
150
121 / C3H6Br
29 / C2H5
107 / C2H4Br
43 / C3H7
71 / C5H11
79 / Br
55 / C4H7
80 / HBr, 16 / CH4
43 / C3H7
C2H4Br
Rearrangment
R
Answers for Student Exercises 1.6 to 1.11 O
E
10
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
43
100
85 / C5H9O
15 / CH3
71 / C4H7O
29 / C2H5
58 / C4H10
42 / C2H2O
57 / C3H5O
43 / C3H7
43 / C3H7
57 / C3H5O
2-Hexanone C6H12O Exact Mass: 100.0888 IHD = 1, match with (h)
O
F
OH Propionic Acid
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
74
74
73 / C3H5O2
1/H
57 / C3H5O
17 / OH
56 / C3H4O
18 / H2O
45 / CHO2
29 / C2H5
C3H6O2 Exact Mass: 74.0368 IHD = 1, match with(c)
G
H2N
OH
prop-2-yn-1-ol C3H4O Exact Mass: 56.0264 IHD = 2, match with (a)
R
Rearrangment
R
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
Rearrangment
73
73
56 / C4H8
17 / NH3
R
55 / C4H7
18 / NH4
R
44 / C2H6N
29 / C2H5
43 / C3H7
30 / CH4N
butan-1-amine C4H11N Exact Mass: 73.0896 IHD = 0, match with (b)
H
Rearrangment
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
55
56 by CI
55 / C3H3O
1/H
39 / C3H3
17 / OH
38 / C3H2
18 / H2O
Rearrangment
Answers for Student Exercises 1.6 to 1.11
I
O N
+
O-
11
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
43
89 by CI
90 / C3H8NO2
Addition of H
72 / C3H6NO
17 / OH
43 / C3H7
46 / NO2
42 / C3H6
47 / HNO2
R
Rearrangment
1-Nitropropane C3H7NO2 Exact Mass: 89.0477 IHD = 1, match with (d)
J
OH O
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
94
138
107 / C7H7O
31 / CH3O
94 / C6H5O
44 / C2H4O
77 / C6H5
61 / C2H5O2
66 / C5H6
72 C3H5O2
51 / C4H3
87 / C4H7O2
39 / C3H2
99 / C5H8O2
2-Phenoxylethanol C8H10O2 Exact Mass: 138.0681 IHD = 4, match with (q)
K O Phenetole
O O Methyl Butyrate
C5H10O2 Exact Mass: 102.0681 IHD = 1, match with (i)
R
R R
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
Rearrangment
94
122
94 / C6H5O
28 / C2H4
R
77 / C6H5
45 / C2H5O
66 / C5H6
56 / C3H4O
51 / C4H3
71 / C4H7O
39 / C3H2
83 / C5H8O
C8H10O Exact Mass: 122.0732 IHD = 4, match with (o)
L
Rearrangment
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
43
102
87 / C4H7O2
15 / CH3
74 / C3H5O2
28 / C2H4
71 / C4H7O
31 / CH3O
59 / C2H3O2
43 / C3H7
43 / C3H7
59 / C2H3O2
Rearrangment R
Answers for Student Exercises 1.6 to 1.11 O
M HN
12
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
Rearrangment
113
113
85 / C5H11N
28 / CO
R
84 / C5H10N
29 / CHO
56 / C4H8
57 / C2H3NO
55 / C4H7
58 / C2H4NO
42 / C3H6
71 / C3H5NO
R
Rearrangment
Caprolactam C6H11NO Exact Mass: 113.0841 IHD = 2, match with (j)
N
N N 2-methylpyrazine
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
94
94
67 / C4H5N
27 / CHN
53 / C3H3N
41 / C2H3N
42 / C2H4N
52 / C3H2N
41 / C2H3N
53 / C3H3N
40 / C2H2N
54 / C3H4N
C5H6N2 Exact Mass: 94.0531 IHD =4, match with (e)
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
152
152
135 / C8H7O2
17 / OH
122 / C7H6O2
30 / CH2O
R
107 / C7H7O
45 / CHO2
R
Methyl salicylate
105 / C7H5O
17 / OH, 30 / CH2O
R
C8H8O3 Exact Mass: 152.0473 IHD = 5, match with (s)
92 / C6H4O
R
77 / C6H5
60 / C2H4O2 17 / OH, 58 / C2H2O2
63 / C5H3
89 / C3H5O3
39 / C3H2
113 / C5H6O3
Fragement Ion 141 / C6H4ClNO
Fragment Loss
127 / C6H4O
30 / NO
111 / C6H4Cl
46 / NO2
99 / C5H4Cl
58 / CNO2
75 / C6H3
46 / NO2, 36 / HCl
50 / C4H2
107 / C2H2ClNO2
O
HO O O
P O N+ -
Cl
O
1-Chloro-4-Nitrobenzene C6H4ClNO2 Exact Mass: 156.9931 IHD = 5, match with (t)
Base Peak
Molecular Ion
75 or 157
157
Rearrangment
Rearrangment
16 / O R
R
Answers for Student Exercises 1.6 to 1.11 Q
O
HO
Br
13
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
60
208 by CI
191 / C7H12OBr
17 / OH
149 / C5H10Br
59 / C2H3O2
129 / C7H13O2
79 /Br
111 / C7H11O
79 /Br, 18 / H2O
R
83 / C6H11
125 / CH2BrO2
R
60 / C2H4O2
147 / C5H9Br
R
Rearrangment
7-Bromo Heptanoic Acid C7H13BrO2 Exact Mass: 208.0099 IHD = 1, match with (w)
R HO 5-Hexyn-1-ol C6H10O Exact Mass: 98.0732 IHD = 2, mathc with (g)
O
S
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
70
98
97 / C6H9O
1/H
83 / C5H7O
15 / CH3
79 / C6H7
19 / H3O
70 / C4H6O
28 / C2H4
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
43
126
111 / C7H11O
15 / CH3
108 / C8H12
18 / H2O
R
93 / C7H9
33 / CH5O
R
83 / C6H11
43 / C2H3O
69 / C5H9
57 / C3H5O
58 / C3H6O
68 / C5H8
55 / C4H7
71 C4H7O
43 / C2H3O
83 / C6H11
6-Methyl-5-hepten-2-one C8H14O Exact Mass: 126.1045 IHD = 2, match with (p)
T O HO Hexanoic acid C6H12O2 Exact Mass: 116.0837 IHD = 1, match with (l)
Rearrangment
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
60
116 by CI
87 / C4H7O2
29 / C2H5
73 / C3H5O2
43 / C3H7
60 / C2H4O2
56 / C4H8
45 / CHO2
71 / C5H11
Rearrangment
R
Rearrangment
R
Answers for Student Exercises 1.6 to 1.11 U HO
Cl
14
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
Rearrangment
162
162
126 / C6H3OCl
36 / HCl
R
98 / C5H3Cl
64 / CHOCl
R
63 / C5H3
99 / CHOCl2
Cl 2,6-Dichlorophenol C6H4Cl2O Exact Mass: 161.9639 IHD = 4, match with (u)
V HO
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
122
122
121/C8H9O
1/H
107/C7H7O
15 / CH3
91 / C7H7
31 / CH3O
77 / C6H5
45 / C2H5O
65 / C5H5
57 / C3H5O
2,6-Dimethylphenol C8H10O Exact Mass: 122.0732 IHD = 4, match with (n)
W
O
2-Cyclohexen-1-one C6H8O Exact Mass: 96.0575 IHD = 3, match with (f)
Rearrangment
Base Peak
Molecular Ion
Fragement Ion
Fragment Loss
Rearrangment
68
96
68 / C4H4O
28 / C2H4
R
55 / C3H3O
41 / C3H5
53 / C4H5
43 / C2H3O
42 / C2H2O
54 / C4H6
R
Answers for Student Exercise 2.1 – 2.9
1
2.1. Since the indicated carbon of phenylacetonitrile is sp3 hybridized, it is reasonable for this compound to show C−H stretching at less than 3000 cm-1 (2960-2940 cm-1). Where as benzonitrile has only aromatic C−H stretching which is typically between 3100 - 3000 cm-1 (page 87).
CH2
N
C
C N
phenylacetonitrile
benzonitrile
2.2. O N
H 2N b. isobutylamine
a. benzonitrile
HO
O
S O
O
c. diphenyl sulfone
d. dioxane
O g. biphenyl
f. formic acid
N+
O
O-
e. 1-nitropropane
HO
H 2N
O
O
h. benzoic acid
i. benzamide
2.3.
1,3-Cyclohexadiene
Diphenylacetylene
Spectrum B
Spectrum A
1-Octene Spectrum D
2-Pentene Spectrum C
2.4. O O
O
NH2 O
H 2N
HO
O O-
C11H23
Na+
Butyl acetate
Butyramide
Isobutylamine
Lauric acid
Sodium propionate
Spectrum E
Spectrum H
Spectrum I
Spectrum F
Spectrum G
2.5. HO
O O Allyl phenyl ether Spectrum L
HO H
Benzaldehyde
Spectrum M
O
o-Cresol Spectrum K
m-Toluic acid Spectrum J
Answers for Student Exercise 2.1 – 2.9
2
2.6. HO
N H 2N
N H 2N
NH2 Cl
N
Aniline
Azobenzene
Spectrum Q
Spectrum O
Benzophenone oxime Spectrum P
2.7.
Methyl isothiocyanate CH3−N=C=S
2.8.
This diketone exists primarily (~ 90%) in enol form (in CCl4) O
O
O
H
Benzylamine Spectrum N
Dimethylamine hydrochloride Spectrum R
O
enol
Enols such as this display broad, shallow O−H stretching bands (here from 3400-2500 cm-1). The strong band at ~1600 cm-1 is the enolic coupled C=C−OH band. (See pages 80, 94, and 98)
Answers for Student Exercise 2.1 – 2.9
3
2.9. O
OH
4-Heptanone
3-Heptanol
4-Bromotoluene
A
B
C
Br
Br
2-Bromopentane
D
O
O
OH
H 2N
OH 2-Hexanone
Propionic Acid
Butylamine
Propargyl alcohol
E
F
G
H
OH
O N+
O-
O
1-Nitropropane
O
O
O 2-Phenoxylethanol
Phenetole
J
K
I
MethylHButyrate
L
HO
O
O
N
HN N
O N+
O
-
Cl
O
Caprolactam
2-methylpyrazine
Methyl salicylate
1-Chloro-4-Nitrobenzene
M
N
O
P
O
O
HO
Br
HO
7-Bromo Heptanoic Acid
5-Hexyn-1-ol
6-Methyl-5-hepten-2-one
R
S
Q
HO
Cl
O
HO
O Cl
HO Hexanoic acid
T
2,6-Dichlorophenol
U
2,6-Dimethylphenol
2-Cyclohexen-1-one
V
W
Answers for Student Exercise 3.1 to 3.3
1 4
3
2
1
Br
(a) 1-bromobutane
3.1(a) 1,2,3,4 are a spin system. Pople notation is A3M2S2X2. 1,2, and 3 are enantiotopic. 3.2 (a) Spin 1 2 3 4
Appr. δ δ 3.40 δ 1.85 δ 1.20 δ 0.85
Table Appendix A, Chart A.1 Appendix A, Chart A.2 Appendix A, Chart A.1 Appendix A, Chart A.1
Coupled with 2 1,3 3, 4 3
Multiplet (n+1) Triplet Quintet Sextet Triplet
Integration 2 2 2 3
3.3 (a)
1
2
3
4
Answers for Student Exercise 3.1 to 3.3
2 5
6
4
1 3
2
7
O O 8
9
(b) (cyclohex-2-enyl)methyl acetate
3.1 (b) 1,2,3,4,5,6,7 are one spin system, and 9 is the second. 4,4’ ; 5,5’ ; 6,6’and 7,7’ are diastereotopic. 3.2 (b) Spin Table or Calculation Coupled with Multiplet (n+1) Integration Appr. δ 1 Appendix A, Chart A.2 6,2,7 Sextet* 1 δ 2.80 2 Appendix D, Chart D2 3,1 Triplet* 1 δ 5.59 3 Appendix D, Chart D2 Quartet* 1 δ 5.59 Appendix D, Chart D2 Quartet** 2 δ 1.96 4 Appendix D, Chart D2 4,6 Quartet** 2 δ 1.65 5 Appendix A, Chart A.2 1,5 Triplet** 2 δ 1.80 6 Appendix A, Chart A.2 1 Doublet** 2 δ 4.05 7 Appendix A, Chart A.1 none Singlet 3 δ 2.10 9 * Coupling constants may not be the same, but make the assumption that they are. **These are diastereotopic, and are coupled to diastereotopic protons, they would not be first order. We will assume they are first order for the drawn spectrum.
3.3 (b)
2
2 and 3
7
1
9
4
6
5
Answers for Student Exercise 3.1 to 3.3
3 2 3
O 1
7 6
4 5
9 8
OH
10
(c) 1-(cyclohexa-1,5-dienyl)-3hydroxy-2-methylpropan-1-one
3.1 (c) 2,3,4,5,6 are a spin system, and 8,9,10 another spin system. 3,3’ ; 4,4’ ; 9,9’ are diastereotopic. 3.2 (c) Spin Table or Calculation Coupled with Multiplet (n+1) Integration Appr. δ 2 Appendix D, Chart D.1 3 Triplet 1 δ 6.68 3 Appendix A, Chart A1 2,4 Quartet*** 2 δ 2.05 4 Appendix A, Chart A1 3,5 Quartet*** 2 δ 2.05 Appendix D, Chart D1 4,6 Quartet* 1 5 δ 5.68 Appendix D, Chart D1 5 Doublet 1 δ 6.22 6 Appendix A, Chart A.1 9,10 Sextet 1 δ 2.65 8 Appendix A, Chart A.1 8 Doublet** 2 δ 3.20 9 Appendix A, Chart A.2 8 Doublet 3 δ 1.05 10 1 δ 0.5-4.0 Appendix E ΟΗ * Coupling constants may not be the same, but make the assumption that they are. ** These are diastereotopic, and are coupled to diastereotopic protons; they would not be first order. We will assume they are first order for the drawn spectrum.
3.3 (c)
2
6
5
9
8
3,4
OH 10
Answers for Student Exercise 3.1 to 3.3
5
4
4
3 2 1 (d) pent-1-yne
H
3.1 (d) 5,4,3 are a spin system and 1 is second. 5,4,3 is Pople notation is A3M2X2; may have long rang coupling. 3+4 are enantiotopic. 3.2 (d) Appr. δ δ 0.85 δ 1.50 δ 2.20 δ 1.80
Spin 5 4 3 1
Table or Calculation Appendix A, Chart A.2 Appendix A, Chart A2 Appendix A, Chart A1 Appendix D, Chart D3
Coupled with Multiplet (n+1) 4 Triplet 3,5 Sextet 4 Triplet none Singlet
3.3 (d)
3
1
4
5
Integration 3 2 2 1
Answers for Student Exercise 3.1 to 3.3
5 O 1
5 6 4 (e) hex-3-en-2-one 2
3
3.1 (e) 3,4,5,6 are a spin system, and 1 is another spin system. Pople notation is A3G2MX. 5 is enantiotopic. 3.2 (e) Appr. δ δ 1.86 δ 6.09 δ 6.82 δ 2.05 δ 1.00
Spin 1 3 4 5 6
Table or Calculation Appendix D, Chart D.2 Appendix D, Chart D.1 Appendix D, Chart D.1 Appendix A, Chart A1 Appendix A, Chart A2
Coupled with Multiplet (n+1) None Singlet 4 Doublet 3, 5 Quartet* 4, 6 Quintet* 5 Triplet
Integration 3 1 1 2 3
* Coupling constants may not be the same, but make the assumption that they are. 3.3 (e)
4
3
5
1
6
Answers for Student Exercise 3.1 to 3.3
6
1
O 2
4 3
5
(f) 1-methoxybut-1-ene
3.1 (f) 3,4,5,6 are a spin system, and 1 is another spin system. Pople notation is A3G2MX. 4 is enantiotopic. 3.2 (f) Appr. δ δ 3.20 δ 6.14 δ 4.63 δ 2.05 δ 1.00
Spin 1 2 3 4 5
Table or Calculation Appendix A, Chart A.1 Appendix D, Chart D.1 Appendix D, Chart D.1 Appendix A, Chart A1 Appendix A, Chart A2
Coupled with Multiplet (n+1) None Singlet 3 Doublet 2, 4 Quartet* 3, 5 Quintet* 4 Triplet
Integration 3 1 1 2 3
* Coupling constants may not be the same, but make the assumption that they are. 3.3 (f)
2
3
1
4
5
Answers for Student Exercise 3.1 to 3.3
7
1
O N 2 O 3 H
4
5
(g) propyl methylcarbamate
3.1 (g) 3,4,5 are a spin system, and 1 is another spin system. Pople notation is A3M2X2. 3 and 4 are enantiotopic. 3.2 (g) Spin Table or Calculation Appr. δ 1 Appendix A, Chart A.1 δ 2.95 3 Appendix D, Chart D.1 δ 4.10 4 Appendix A, Chart A.2 δ 1.60 5 Appendix A, Chart A1 δ 0.85 NH δ 4.5-7.5 Appendix E *See Section 3.6.2 for coupling between 1 and N-H.
Coupled with Multiplet (n+1) None Singlet 3 Triplet 2, 4 Sextet 3, 5 Triplet * Singlet
Integration 3 2 2 3 1
3.3 (g)
NH
3
1
4
5
Answers for Student Exercise 3.1 to 3.3
8
1
2 O 3 O (h) diethoxymethane
3.1 (h) 1 and 2 are a spin system, and 3 is another spin system. Pople notation is A3X2. 2 are enantiotopic. 3.2 (h) Spin 1 2 3
Appr. δ δ 1.20 δ 3.40 δ 4.95
Table or Calculation Appendix A, Chart A.2 Appendix A, Chart A.1 Appendix B, Table B.1
Coupled with Multiplet (n+1) 2 Triplet 1 Quartet none Singlet
Integration 3 2 2
3.3 (h)
3
2
1
Answers for Student Exercise 3.1 to 3.3
9
1
HO
6 2
3
4
5
(i) 2-methylpentan-2-ol
3.1 (i) 3,4 and 5 is a spin system. 1 and 6 are enantiotopic to each other and 3 and 4 are also enantiotopic. Pople notation is A3M2X2. 3.2 (i) Spin 1 and 6 3 4 5 ΟΗ
Appr. δ δ 1.20 δ 1.50 δ 1.20 δ 0.85 δ 0.5-4.0
Table or Calculation Appendix A, Chart A2 Appendix A, Chart A2 Appendix A, Chart A1 Appendix A, Chart A2 Appendix E
Coupled with Multiplet (n+1) none Singlet 4 Triplet 3,5 Sextet 4 Triplet none Singlet
3.3 (i)
1 and 6 Large singlet of 6 H
OH
3
1,6,4
Integration 6 2 2 3 1
Answers for Student Exercise 3.1 to 3.3
10
1
S 2
3
S
(j) 1,4-bis(methylthio)butane
3.1 (j) Not First order (no Pople). See Section 3.11.2. Protons 2 and 3 are enantiotopic. Protons on 1,2,3 are Chemical Shift Equivalent. 3.2 (j) Spin Table or Calculation Coupled with Multiplet (n+1) Appr. δ 1 Appendix A, Chart A1 none Singlet δ 2.10 2 Appendix A, Chart A1 3 Triplet* δ 2.60 Appendix A, Chart A2 2,3 Quintet* 3 δ 1.60 * Would not be first order. We will assume they are first order for the drawn spectrum.
Integration 6 or 3 4 or 2 4 or 2
3.3 (j)
Actual spectrum would look like this!
2
PPM
1
0
Answers for Student Exercise 3.1 to 3.3
11
3' 4
2'
O 1
5
6
N
2
7 3 (k) N,N,4-trimethylbenzamide 8
3.1 (k) 2,2’; 3,3’ are CSE but not ME. 6 and7 are diastereotopic. Pople notation for ring is AA’ XX’ 3.2 (k) Spin Table or Calculation Coupled with Multiplet (n+1) Appr. δ 2, 2’ Appendix D, Chart D1 none Doublet** δ 7.80 3, 3’ Appendix D, Chart D1 3 Doublet** δ 7.25 6,7 Appendix A, Chart A1 none Singlet* δ 2.95 8 Appendix A, Chart A1 none Singlet δ 2.25 * There will be two singlets because of the restricted rotation of the NR2 ** These can not be first order. Not magnetically equivalent. 3.3 (k)
2,2’
3,3’
6,7
8
Integration 2 2 6* 3
Answers for Student Exercise 3.1 to 3.3
12
6 5
O 1 7
8
2
4
OH 3 (l) 1-(2-hydroxyphenyl)ethanone
3.1 (i) N.A. 3.2 (i) Spin Table or Calculation Appr. δ 3 Appendix D, Chart D.1 δ 6.85 4 Appendix D, Chart D.1 δ 7.05 5 Appendix D, Chart D.1 δ 7.25 6 Appendix D, Chart D.1 δ 7.70 8 Appendix A, Chart A1 δ 2.40 OH δ 5.5-12.5 Appendix E * Will have long range coupling.
Coupled with Multiplet (n+1) 4 Doublet* 3,5 Triplet* 4,6 Triplet* 5 Doublet* none Singlet none Singlet
3.3 (i)
OH
6
5
4
3
8
Integration 1 1 1 1 3 1
Answers for Student Exercise 3.1 to 3.3
13
Cl 1
2 H
O (m) 2-chloroacetaldehyde
3.1(m) 1 and 2 is a spin system. Pople notation is A2X. 2 protons are enantiotopic. 3.2 (m) Spin 1
Appr. δ δ 4.95
Table Coupled with Multiplet (n+1) Appendix A, Chart A.1 2 Triplet Plus Appendix B, Table B.1* 2 Appendix D, Chart D.6 1 Doublet δ 9.80 extrapolation Calc is based on Chart A1 3.45 for ClCH2 plus Table B.1 value of 1.50 for HC=O
3.3 (m)
2
1
Integration 1 2
Answers for Student Exercise 3.1 to 3.3
14
2H
3
1
H
H
F (n) fluoroethene
3.1(n) Charts are not available in text for this problem. Pople notation is AGMX, where X is F. 3.2 (n)
3.3 (n)
7
6
5
4 PPM
3
2
Protocol of the H-1 NMR Prediction: Node
Shift
H
4.85
H
6.79
H
4.23
Base + Inc. 5.25 -0.40 5.25 1.54 5.25 -1.02
Comment (ppm rel. to TMS) 1-ethylene 1 -F cis 1-ethylene 1 -F gem 1-ethylene 1 -F trans
1
0
Answers for Student Exercise 3.1 to 3.3
15
3' 4
2'
O
1
O
5
2
6
3 (o) cyclohexyl acetate
3.1 (o) 1,2,2’,3,3’, and 4 is a spin system, and 6 is another spin system. 2,2,;2’,2’;3,3;3’,3’;4,4 protons are diastereotopic. 2 and 2’ are CSE, also 3 and 3’ are CSE. 3.2 (o) Spin Table or Calculation Coupled with Multiplet (n+1) Integration Appr. δ 1 Appendix A, Chart A.1 2,2’ Quintet 1 δ 4.95 2,2’ Appendix A, Chart A.2 1,(3or3’) Quartet* 4 δ 1.60 3,3’ Appendix C, Table C.1 (2 or 2’),4 Quintet* 4 δ 1.44 4 Appendix C, Table C.1 3,3’ Quintet* 2 δ 1.44 6 Appendix A, Chart A.1 none Singlet 3 δ 2.00 * These are diastereotopic, and are coupled to diastereotopic protons; they would not be first order. We will assume they are first order for the drawn spectrum. 3.3 (o)
4
1
6
2,2’
3,3’, and 4
Answers for Student Exercise 3.4
16
Problem Problem 3.4 4.3 A A C7H14O
1
O 1
2
3
3
4 4-Heptanone
2
ppm
2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 1.0 0.9 0.8 Problem 3.4 4.3 B B C7H16O Problem
OH 1
OH
2
3 4 5 6
1
7
2
3-Heptanol
3
4
5
6
3.5
3.0
Problem 4.3 C C H Br Problem 3.4 C 7 7 5
2.5 2 1
2.0
1.5
7
ppm
1.0
3 4
5
Br
4-Bromotoluene
3
2
7.5
7.0
6.5
6.0
Problem 3.4 4.3 D D C5H11Br Problem
5.5
5.0
4.5
4.0
3.5
3.0
2.5
1
Br
ppm
5
3 5 4 2 2-Bromopentane
1
2 3
4.0
3.5
3.0
2.5
2.0
4
1.5
1.0
ppm
Answers for Student Exercise 3.4 1 Problem Problem 3.4 4.3 E E C6H12O
17 O 3 5 2 4 2-Hexanone
1
3
6
6
4
5
2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 1.0 0.9 0.8
ppm
O
Problem 3.4 4.3 FF C3H6O2 Problem x4
HO 1
2
3
3
Propionic Acid
OH
2
12.0
ppm
11.5
3.5
3.0
2.5
2.0
ppm
1.5
Problem 3.4 4.3 G G C4H11N Problem
H2N 1
2
3
4
4
Butylamine
1
NH2 2
3
2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 1.0 0.9 0.8 Problem 33.4 4.3 HH C3H4O Problem 1
OH
3 Propargyl alcohol
3
4.4
2
OH
1
4.2
4.0
3.8
3.6
3.4
ppm
3.2
3.0
2.8
2.6
2.4
2.2
2.0
ppm
Answers for Student Exercise 3.4 Problem 3.4 I Problem 4.3 I C3H7NO2 O N+ 1 2 O
18
3
3
1-Nitropropane
1
4.5
4.0
2
3.5
3.0
3
Problem 3.4 J Problem 4.3 J C8H10O24 3
2 1
6
5
2.5
OH
2.0
1.5
5
2
1.0
ppm
6
4
O 2-Phenoxylethanol 2200
2150
Hz
2100
1250
1200
1150
Hz
OH
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
ppm
Problem Problem 3.4 4.3 K K C8H10O 6
3
7.5
2
7.0
3
2 5
4
O
1
6
5
4
Phenetole
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
1.5 ppm
2.0
Problem Problem 3.4 4.3 L L C5H10O2 O O 1 2 3 5
5
4
2
4
3
Methyl Butyrate
3.5
3.0
2.5
2.0
1.5
1.0
ppm
Answers for Student Exercise 3.4
2
19
4
Problem Problem 3.4 4.3 M M C6H11NO
5 3
6
O HN 1 2
NH
6
5 4
3
Caprolactam
7.0
6.5
6.0
5.5
5.0
4.5
Problem 3.4 4.3 N N aCpyrazine 5H6N2 A pyrazine Problem 3
4.0
3
3.0
2.5
1.5 ppm
2.0
N
2
7
3.5
4 5
7
N
6 1 2-methylpyrazine
6
5 2520
8.5
8.0
7.5
2510
7.0
6.5
2500
6.0
5.5
HO
Problem Problem 3.4 4.3 O O C8H8O3 3
1 proton (x32)
5 O
OH 13
O
12
7.5
Hz
2490
7
5.0 1
4.5
3.5
ppm
3.0
4
6
2
4.0
5
8
6
3 4 8 Methyl salicylate
ppm
7.0
6.5
Problem Problem 3.4 4.3 PP C6H4ClNO2 3
2300
2250
2200
6.0
5.5
5.0
3
O -
O
4.5
Hz
4.0
ppm
7.3
ppm
2
2 1
N+ 4
2150
Cl
1-Chloro-4-Nitrobenzene
8.2
8.1
8.0
7.9
7.8
7.7
7.6
7.5
7.4
Answers for Student Exercise 3.4 Problem 3.4 Q Problem 4.3 Q C7H13BrO2 Acid OH 1 proton (x32)
20 O 2
HO 1
7
3
4
5
6
7 Br
7-Bromo Heptanoic Acid
2 12
6
5 4
ppm
11
4.5
4.0
3.5
3.0
2.5
2.0
2
HO 1
4
3
5
6
5-Hexyn-1-ol
1
4
OH
3.4
3.2
3.0
ppm
1.5
6
Problem 4.3 3.4 R R C6H10O Unsaturated alcohol
3.6
3
2.8
2.6
Problem ketone ketone Problem 3.4 4.3 SS Unsaturated C8H14O Unsaturated
2.4
2 3
2.2
2.0
1.8
1
8
O
ppm
1.6
5 3 2 4 6 7 6-Methyl-5-hepten-2-one
1
78 3
5
1520
5.0
4.5
4.0
Problem Problem 3.4 4.3 T T C6H12O2
1510
1500
4
Hz
3.5
3.0
2.5
1.5 ppm
2.0
O
2
HO 1
OH
2
3
4
5
Hexanoic acid
6
4
5
6
3 13
12
2.8
ppm
2.6
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
ppm
Answers for Student Exercise 3.4
21
Problem 4.3 3.4 U U C6H4OCl2
3
OH HO
4
Cl
1
2 3
Cl
4 2,6-Dichlorophenol
ppm
7.5 7.4 7.3 7.2 7.1 7.0 6.9 6.8 6.7 6.6 6.5 6.4 6.3 6.2 6.1 6.0 5.9 5.8 5.7
HO
3
Problem 4.3 Problem 3.4 V V C8H10O
5 1
2
4
3
5
4 2,6-Dimethylphenol
2120
2100
2080
2060
Hz
4.5
4.0
3.5
OH
7.0
6.5
6.0
5.5
5.0
3.0
ppm
2.5
Problem 4.3 3.4 W W Unsaturated ketone ketone C6H8O Unsaturated 6
4
5
O 1 6
3
2
5
4
2 3
2-Cyclohexen-1-one
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0 ppm
22 Answers for Student Exercise 3.5
3.5A. (1.58(300) – 0.90(300))/7 = about 29; (2.36(300) – 1.58(300))/7 = about 33 3.5E. (2.38(300) – 1.52(300))/7 = about 37; (1.52(300) – 1.38(300))/7 = about 6 (1.38(300) – 0.87(300))/7 = about 22 3.5F. (2.38(300) – 1.13(300))/7 = about 54 3.5G. (2.61(300) – 1.35(300))/7 = about 54; (1.35(300) – 1.29(300))/7 = about 2 to 3 (1.29(300) – 0.84(300))/7 = about 19 3.5H. Long range coupling; can’t measure coupling constant 3.5I.
(4.33(300) – 2.01(300))/7 = about 99; (2.01(300) – 0.99(300))/7 = about 44
3.5K. (4.08(300) – 1.44(300))/7 = about 113 3.5L. (2.26(300) – 1.62(300))/7 = about 27; (1.62(300) – 0.92(300))/7 = about 30 3.5Q. (3.39(300) – 1.86(300))/7 = about 66; (2.36(300) – 1.65(300))/7 = about 30 (1.86(300) – 1.47(300))/7 = about 17; (1.65(300) – 1.37(300))/7 = about 12 3.5U. (7.25(300) – 6.81(300))/9 = about 15
Answers for Student Exercises 3.6
23 O 1
3
2
4 4-Heptanone
A Pople Notation -- A3M2X2; 2 and 3 (and 5 and 6) are enantiotopic. 3 and 5, 2 and 6 are CSE. 1
OH
2
3 4 5 6
7
3-Heptanol
B One spin system. 2,2’; 4,4’; 5,5’, and 6,6’ are diastereotopic. 3
2 5
1
4
Br
4-Bromotoluene
C Two spin systems. Pople Notation -- AA’XX’. 2 and 2’ are CSE but not magnetically equivalent as are 3 and 3’.
Br 3 5 4 2 2-Bromopentane
1
D One spin system. 3 and 3’; 4 and 4’ are diastereotopic.
O 1
3 5 2 4 2-Hexanone
E
Two spin systems. 3, 4, and 5 are enantiotopic. O HO 1
2
3
Propionic Acid
F
A3X2. Protons on two are enantiotopic.
6
Answers for Student Exercises 3.6
24 2
H2N 1
4
3
Butylamine
G Pople Notation – A3G2M2X2One spin system. 1, 2, and 3 are enantiotopic. 1
OH
2
3 Propargyl alcohol
H One spin system with long range coupling. Protons on 2 enantiotopic.
O -
O
N+ 1
3
2
1-Nitropropane
I
Pople Notation -- A3M2X2. 1 and 2 are enantiotopic. 3 4 3'
2 1
5
6
OH
O
2' 2-Phenoxylethanol
J Two spins systems; Pople Notation -- AA’MM’X and A2X2. 2 and 2’are CSE but not magnetically equivalent as are 3 and 3’. 5 and 6 are enantiotopic. 6
2 5
O
3
1
4
2' 3' Phenetole
K Two spins systems; Pople Notation -- AA’MM’X and A3X2. 2 and 2’are CSE but not magnetically equivalent as are 3 and 3’. 5 and 6 are enantiotopic. O O 1 2 3 5
4
Methyl Butyrate
L Two spin systems; Pople Notation --A3M2X2. 2 and 3 are enantiotopic.
Answers for Student Exercises 3.6
25 O HN 1 2 6
3
5 4
Caprolactam
M One spin system. 2,2’; 3,3’; 4,4’; 5,5’ and 6,6’ are diastereotopic. 4
3
N
2
7
5
N
6 1 2-methylpyrazine
N Pople Notation –AB for 5 and 6. Three spins systems. HO O O
1
6
2
7
5
3 4 8 Methyl salicylate
O
Two spin systems. Pople Notation – AGMX. 3
O -
2 1
N+ 4
Cl
O 3' 2' 1-Chloro-4-Nitrobenzene P One spin system. 2 and 2’ are CSE but not magnetically equivalent as are 3 and 3’.
O HO 1
2
3
4
5
6
7-Bromo Heptanoic Acid
Q One spin system. 2, 3, 4, 5, 6, and 7 are enantiotopic.
7 Br
Answers for Student Exercises 3.6
26 6 2
HO 1
3
4
5
5-Hexyn-1-ol
R One spin system with long range coupling. 1, 2, 3, and 4 are enantiotopic. 8
O
5 3 2 4 6 7 6-Methyl-5-hepten-2-one
1
S At 2 spins systems (7 and 8 probably have long range coupling). 3 and 4 are enantiotopic.
O 2
HO 1
3
4
5
6
Hexanoic acid
T
One spin system. 2, 3, 4, and 5 are enantiotopic. HO
1
Cl 2 3
Cl
3' 4 2,6-Dichlorophenol
U One spin system. 3 and 3’ are CSE but not magnetically equivalent.
HO
5 1
2
6
3
3' 4 2,6-Dimethylphenol
V One spin system. 3 and 3’ are CSE but not magnetically equivalent. 5 and 6 are CSE. O 1 6 5
4
2 3
2-Cyclohexen-1-one
W
One spin system. 4, 5, and 6 are enantiotopic.
Answers for Student Exercise 3.7
A
X
JAX
JXA
1
AX
27
1
1
A
1 JXA
JAX 1
A2X
1 1
A2
X
1 2
1
X
1 X
JXA 1 JAX 1
A3X
1
3
A2X2
3
1
1 2
1
1 1
JXA
JAX 1
1 2
1 1
A3
1
JXA JAX 1 A3X2
1
1
2
1
1
A3
1 2
1
1
3
X2
1 2
1
1
A2
1 3
1
X2
Answers for Student Exercise 3.8
28
With the AMX systems A and X do not change; they are represented as follows: JAM JMX 1
1
1
1
JAM
AMX 1
1 A
2
1
1
M
X
JMX
JAM 1 2
1 1
A2MX
A2
1
3
1
JAM
1
A3MX
1
1
3 4
JMX
A3
2
1
1 3
6
X
1 3
1
M
1 4
1 JMX
M
X
29
Answers for Student Exercise 3.8 Continued JAM
A2MX2 1
3
1
4
M
X2
1 2
1 1
A2
1 3
6
JMX
1 4
1
JAM M
1
A2MX3
1 A2
2
1 1 1 1
3 4
1 JMX
3 6
10
5
4 10
1 5
1
JAM
A3MX3
1
1 1 1 1
6
1
3 4
15
1 3
6 10
5
A3
2
1
1 4
10 20
X3
1
1 5
15
JMX 1
6
1
M
X3
30
Answers for Student Exercise 3.9 With the AMX systems A and X do not change; they are represented as follows: JAM JMX 1
1
1
1
The following are for M: JAM
AMX 1 1
1 1
1
1
JMX
A2MX JAM 1
1 2
1 1
1
2
A3MX
1 2
1 JMX
1
JAM 1
1 2
1 1 1
1
3 1
3
1
3 3
3
3
1
1
JMX
31 Answers for Student Exercise 3.9 Continued JAM
A2MX2 1
1
1
2
1 1
1 2
1 2
2 4
3
A2MX3
JMX
1 1 3
1
2
JAM 1
1 2
1 1
1 1 1
2
2
2 3
4 7
5
3
1 1 3
1
2 5
7
JMX
1
1
3
JAM
A3MX3
1
1 2
1 1 1 1 1
3 1
2 3
1
3 4
6
3 3
6 10
3 6
12
3 6
12
1
4 10
1
1 2 6
JMX 1
3
1
32 Answers for Student Exercise 3.10A
Spin System ab2c3 Coupling a-b 6 Hz b-c 12Hz a-c 3 Hz
1
1
(c)
1
1 Jcb
2
1 1
2
1
1 2
1 1 (b)
1
1
3 1
1 Jca
1
2
3
3
3
3
1 1
1 2
3
2 3
5
1
2 4
7
Jab
1
2
1 (a)
3
1
1
1
1
1 3
7
1 2
5
1 3
Jac 1
Jbc 1
Jba
33
Answers for Student Exercise 3.10B
Spin System ab2c3 Coupling a-b 6 Hz b-c 4Hz a-c 9 Hz
1 (c)
1 Jca
1
1
1
1
2
1
1
1
1 1
1 1
(b)
1 Jcb
2 1
1
1
Jba 1
2 1 1 2
Jbc 1
3 1 3 3 1 3
1
1
1
1
2
1
(a)
1 1 1
2
3 1
3
3
1
6
3 3
3
3
3
6
1 3
1
1
3
Jac 1 Jab
2
1
34
Answers for Student Exercise 3.10C
Spin System a2b2c2 Coupling a-b 6 Hz b-c 4Hz a-c 9 Hz
1 Jca
1
(c)
1
1 1
1 2
1 1 1
2
4
1
1 2
2 1
1 Jbc
2 2 1 4 1 2 2
1 2
1
2
1 Jba
2
1
1
1
1
1
1
1
(a)
1 Jcb
1
2
2
2
(b)
1
2
1
1 Jac
2 1
2
2
1
4
2
1
1
2
1 2
Jab 1
Answers for Student Exercise 4.1
1
O
2 1
1
OH
2 O
1
O 2
1
S 2
3
3
1 2 S
2' 1'
O
2
1
1
N 1'
j
h
c
2'
2
OAc 2
1 o
k
Answers for Student Exercise 4.2 - 3 (a)
a 3
4
1 Br
2
1-bromobutane Atom C1
Base
α
β
γ
δ
Other
0
α-Br
Methane
2
3
4
-2.5
9.1
9.4
-2.5
C2
Methane
1,3
4
-2.5
18.2
9.4
11
C3
Methane
4,2
1
γ-Br
-2.5
18.2
9.4
C4
Methane
3
2
1
-2.5
9.1
9.4
-2.5
45
40
35
0
ε
Calc Shift
20
are from Table 4.4
33.5
Other is from table 4.6
β-Br 36.1
−3
30
Comments The base and shifts
22.1 13.5
25
20
15
10
5
ppm
Answers for Student Exercise 4.2 - 3 (b)
5
2
6 1
4
7 3
2
O O
8
9
CH3
(b) (cyclohex-2-enyl)methyl acetate α
β
Methane
2,6,7
OCOR,3,5
4
3°(3(2°))
-2.5
3*9.1
6+9.4+9.4
-2.5
3*(-3.7)
value
-2.5
27.3
24.8
-2.5
-11.1
C2
ethylene
1,4'
6,7,5'
5,6'
γ-OCOR, Zcis (-3)+(-1.1)
Atom
Base
C1
C3
C4
C5
δ
ε
Other
10.6+-7.9
7.2+7.2+-1.8
(-1.5)+(-1.5)
123.3
2.7
12.6
-3
-4.1
ethylene
4,1'
5,6',7'
6,5'
Zcis -1.1
10.6+-7.9
7.2+2(-1.8)
(-1.5)+(-1.5)
123.3
2.7
3.6
-3
Methane
3,5
6,2
1,1
7
2(9.1)
2(9.4)
2(-2.5)
0.3
-2.5
18.2
18.8
-5
0.3
Methane
4,6
1,3
7,2,2
2(9.1)
2(9.4)
3(-2.5)
18.2
18.8
-7.5
-2.5 C6
γ
Methane -2.5
2,4,7
2(3),OCOCH3
3(9.4)
2(-2.5)+(-3)
-2.5
18.2
28.2
-8
-2.5
6,2
3,5
4
2°(3°)
15.2
-4
0.3
-2.5
C8
Table 4.12
C9
Table 4.12
61
20.7
140
120
Other is from table 4.6
are from Table 4.4
131.5
125.5
2°(3°)
170.5
160
36
27
1,5
Table 4.12 1,OCOCH3
Comments The base and shifts
29.8
2(9.1) C7
-2.5
-1.1
Calc Shift
100
80
60
33.4 67.5 170.5
Table 4.12
20.7
Table 4.12
40
20
ppm
3
Answers for Student Exercise 4.2 - 3 (c)
O 1 4
5
6
2
7 OH 8
3
(c) 3-hydroxy-2-methyl1-phenylpropan-1-one
Atom
δ
from table 4.12
Base
ε
Other
Calc Shift
Table 4.12 C1
128.5
7.8
136.3
C2
128.5
-0.4
128.1
C3
128.5
-0.4
128.1
C4
128.5
2.8
131.3
From Table 4.19 the C=O is approximately 197.6 ppm,
C5 C6
C7
C8
α
β
methane
7,8,5
OH,Ph
3°(2°,3°)
-2.5
2(9.1)+24
10+9
(-3.7)+(-9.5)
-2.5
42.2
19
-13.2
methane
OH, 6
8, 5
1
2°(3°)
-2.5
48+9.1
9.4+1
-2
-2.5
-2.5
57.1
10.4
-2
-2.5
methane
6
7,5
OH,Ph
1°(3°)
-2.5
9.1
9.4+1
(-5)+(-2)
-1.1
-2.5
9.1
10.4
-7
-1.1
180
160
140
δ
120
ε
198
Base
200
γ
100
Comments These compare nicely
Other
80
Calc Shift
Table 4.4 + Table 4.6
45.5
60.5
8.9
60
40
20
ppm
Answers for Student Exercise 4.2-3 (d)
4
5
4
3 2
1
H
(d) pent-1-yne
α
β
γ
δ
ε
Atom
Base
Other
C1
Table 4.11
Comments The base and shifts
67.0-68.1
are from Table 4.11
67.6 C2
Calc Shift
Increments from table 4.6
67.6
Table 4.11 84.7-84.5 84.6
C3
C4
C5
84.6 4,c≡
5,c≡
9.1+4.5
9.4+5.5
-2.5
13.6
13.9
Methane
5,3
c≡
2(9.1)
5.5
-2.5
18.2
5.5
Methane
4
3
γ-c≡
-2.5
9.1
9.4
-3.5
-2.5
9.1
9.4
-3.5
Methane
85
80
75
70
65
Base shifts Table 4.4 25
21.2
60
55
50
45
40
35
12.5
30
25
20
15
10
ppm
Answers for Student Exercise 4.2-3 (e)
5
O 1
α
β
5 6 4 (e) hex-3-en-2-one 2
γ
3
δ
ε
Atom
Base
C1
methane
2
3
4
5
6
Comments The base and shifts
-2.5
24
9.4
-2.5
0.3
0.1
are from Table 4.4
-2.5
24
9.4
-2.5
0.3
0.1
Table 4.10
1,3
3
4
6
C2
Other
Calc Shift
28.8
Table 4.10
196.9 C3
C4
C5
C6
approximate
196.9
ethylene
2,5'
6'
123.3
24+(-7.9)
-1.8
123.3
16.1
-1.8
ethylene
5,2'
6
123.3
10.6+1
7.2
137.6
123.3
11.6
7.2
methane
6,4
3
2
1
-2.5
2(9.1)
9.4
-2
0.3
-2.5
18.2
9.4
-2
0.3
142.1
2
1
0.3
0.1
methane
5
4
3
-2.5
9.1
9.4
-2.5
-2.5
9.1
9.4
-2.5
140
120
180
Increments from Table 4.6
160
100
23.4
13.9
80
60
40
20
ppm
6
Answers for Student Exercise 4.2-3 (f)
1
O 2
4 3
5
(f) (1-methoxybut-1-ene
Atom C1
C2
C3
C4
C5
α
Base
β
γ
δ
ε
Other
Comments
Calc Shift
methane
O-R
2
3
4
5
The base and shifts
-2.5
51
9.4
-2.5
0.3
0.1
are from Table 4.4
-2.5
51
9.4
-2.5
0.3
0.1
55.8
Increments from table 4.6
Table 4.10 153.2
4'
5'
153.2
-7.9
-1.8
Table 4.10
4
5
84.2
10.6
7.2
Table 4.10 143.5
84.2
10.6
7.2
methane
5,3
2
γ-OR
102
-2.5
9.1+9.1
9.4
-2
-2.5
18.2
9.4
-2
23.1
methane
4
3
2
1
-2.5
9.1
9.4
-2.5
0.1
-2.5
9.1
9.4
-2.5
0.1
140
130
120
110
100
90
80
70
13.6
60
50
40
30
20
ppm
Answers for Student Exercise 4.2-3 (g)
7
O
1
4
N 2 O 3 H
5
(g) propyl methylcarbamate Comments
Atom
Base
α
β
γ
δ
ε
C1
methane
NH
COO
3
4
5
The base and shifts
-2.5
31
2
-2.5
0.3
0.1
are from Table 4.4
-2.5
31
2
-2.5
0.3
0.1
Other
Calc Shift
28.4
Increments from table 4.6
C2 Table 4.20
Table 4.20
157.8 C3
C4
C5
157.8
methane
3,OCOR
5
NHR
-2.5
9.1+51
9.4
-4
-2.5
60.1
9.4
-4
methane
5,3
OCOR
-2.5
9.1+9.1
5
-2.5
18.2
5
methane
4
3
OCOR
-2.5
9.1
9.4
-3
-2.5
9.1
9.4
-3
150
140
130
120
63
20.7
110
100
13
90
80
70
60
50
40
30
20
ppm
Answers for Student Exercise 4.2-3 (h)
1
8
2 O 3 O (h) diethoxymethane
Atom
Base
α
β
C1
methane
2
OCOR
Comments The base and shifts
-2.5
9.1
5
are from Table 4.4
-2.5
9.1
5
methane
1,OCOR
3
-2.5
9.1+45
9.4
-2.5
54.1
9.4
methane
2(OR)
2(2)
2(1)
-2.5
51(2)
9.4(2)
2(-2.5)
-2.5
102
18.8
-5
110
100
C2
C3
90
γ
δ
ε
Other
Calc Shift
11.6
Increments from table 4.6 See Table 4.15 for comparison
61
80
113.3
70
60
50
40
30
20
10
ppm
9
Answers for Student Exercise 4.2-3 (i)
6
1
HO
2
3
5
4
(i) 2-methylpentan-2-ol Atom
Base
α
β
γ
δ
C1
methane
2
6,3,OH
4
5
1°(4°)
-2.5
9.1
2(9.4)+10
-2.5
0.3
C2
C3
C4
C5
C6
ε
0.3
Other
Calc Shift
Comments The base and shifts
-3.4
are from Table 4.4 29.8
Increments from table 4.6
-2.5
9.1
28.8
-2.5
methane
1,6,3,OH
4
5
-3.4 4°(2(1°)+2°)
-2.5
3(9.1)+48
9.4
-2.5
(2)(-1.5)+-8.4
-2.5
75.3
9.4
-2.5
-11.4
methane
2,4
1,6,OH,5
2°(4°)
-2.5
9.1(2)
3(9.4)+10
-7.2
-2.5
18.2
38.2
-7.2
methane
3,5
2
1,6,OH
-2.5
2(9.1)
9.4
2(-2.5)+(-5)
-2.5
18.2
9.4
-10
methane
4
3
2
1,6
-2.5
9.1
9.4
-2.5
(2).3
-2.5
9.1
9.4
-2.5
0.6
2
6,3,OH
4
5
1°(4°)
-2.5
9.1
2(9.4)+10
-2.5
0.3
-3.4
-2.5
9.1
28.8
-2.5
0.3
-3.4
100
90
80
70
comparison 68.3
46.7
15.1
methane
110
See Table 4.14 for
60
14.1
50
29.8
40
30
20
10
ppm
10
Answers for Student Exercise 4.2-3 (j)
1
S 2
S
3
(j) 1,4-bis(methylthio)butane
Atom
Base
α
C1
methane
SR
Comments The base and shifts
-2.5
20
are from Table 4.4
-2.5
20
methane
SR,3
3
2
SR
See Table 4.18 for
-2.5
20+9.1
9.4
-2.5
0
Comparison
-2.5
29.1
9.4
-2.5
methane
2,2
3,SR
2
SR
-2.5
2(9.1)
9.4+7
-2.5
0
-2.5
18.2
16.4
-2.5
35
30
C2
C3
45
40
β
γ
δ
ε
Other
Calc Shift
17.5
Increments from table 4.6
33.5
29.6
25
20
15
10
5
ppm
11
Answers for Student Exercise 4.2-3 (k)
O 1 4
5
6
N
2
8
7
3 (k) N,N,4-trimethylbenzamide Atom
Base
δ
from table 4.12
Table 4.12 C=ONH2
ε
Other
Calc Shift
CH3
C1
128.5
5
-2.9
130.6
C2
128.5
-1.2
-0.1
127.2
C3
128.5
0
0.7
129.2
C4
128.5
3.4
9.3
141.2
From Table 4.20 the C=O is approximately 171 ppm,
C5 C6
C7
Base
α
β
γ
methane
NR2
C=O
Ph
-2.5
42
1
-2
-2.5
42
1
-2
methane
NR2
C=O
Ph
-2.5
42
1
-2
-2.5
42
1
-2
δ
ε
171 Other
Calc Shift
Table 4.4 + Table 4.6
38.5
38.5
C8 Table 4.12
160
Comments Table 4.12
Table 4.12
21.3
140
120
100
80
60
40
20
ppm
12
Answers for Student Exercise 4.2-3 (l)
6 5
O 1
8
7 2
4
OH 3 (l) 1-(2-hydroxyphenyl)ethanone
Atom
Base
δ
from table 4.12
Table 4.12 C=OCH3
ε
Other
Calc Shift
OH
C1
128.5
7.8
-12.7
123.6
C2
128.5
-0.4
26.6
154.7
C3
128.5
-0.4
-12.7
115.4
C4
128.5
2.8
1.6
132.9
C5
128.5
-0.4
-7.3
120.8
C6
128.5
-0.4
1.6
129.7
C7
From Table 4.19 the C=O is approximately 197.6 ppm,
197.6
C8
From Table 4.19 the CH3 is approximately 26.3 ppm,
26.3
180
160
140
120
100
80
60
Comments Table 4.12
Table 4.19
40
20
ppm
13
Answers for Student Exercise 4.2-3 (l)
Cl
1
2 H
O (m) 2-chloroacetaldehyde
Atom
Base
α
β
γ
δ
ε
C1
methane
Cl, CHO
Comments The base and shifts
-2.5
31+31
are from Table 4.4
-2.5
62
Other
Calc Shift
59.5
C2 Table 4.19
Increments from table 4.6 See Table 4.18 for
Cl
Comparison
199.7 199.7
200
199.7
180
160
140
120
100
80
60
40
20
ppm
14
Answers for Student Exercise 4.2-3 (n)
2
H
H
1
H
F (n) fluoroethene
Atom
Base
α
C1
Ethylene
F
Comments The base
123.2
68
are from Table 4.9
123.2
68
C2
β
γ
δ
ε
Other
Calc Shift
191.2
Increments from table 4.6
Ethylene
F
See Table 4.9 for
123.2
9
Comparison
123.2
9
132.2
Note -- These are not close to observed values, but are the only answer from given tables.
19F couplings not shown
200
180
160
140
120
100
80
60
40
20
ppm
15
Answers for Student Exercise 4.2-3 (n)
O
1 2
4
O
5 6
3 (o) cyclohexyl acetate Atom
Base
α
C1
Table 4.7
OCOR
Comments The base and shifts
26.9
51
are from Table 4.7
26.9
51
C2
C3
C4
C5
β
γ
δ
ε
Other
Calc Shift
Increments from table 4.6
77.9
Table 4.7
OCOR
26.9
6
26.9
6
32.9
Table 4.7
OCOR
26.9
-3
26.9
-3
23.9
Table 4.7
OCOR
26.9
0
26.9
0
26.9
Table 4.20 Approx 168
C6
methane
COO
1
2,2
3,3
Table 4.20 The base and shifts
-2.5
25
-2.5
2(.3)
2(.1)
are from Table 4.4
-2.5
25
-2.5
0.6
0.2
160
168
140
120
100
80
Increments from table 4.6
20.8
60
40
20
ppm
Answers for Student Exercise 4.4 A-C
16
O
Problem Problem 5.7A 4.4 A
1
3
2
4 4-Heptanone
3
2
1
4 200
180
160 1
Problem 5.7B 4.4 B Problem
140 OH
2
120
100
80
60
40
20
ppm
7
3 4 5 6 3-Heptanol
2
3
85
80
75
70
65 5
Problem Problem 5.7C 4.4 C
60
2
55
50
3
1
4
45
40
4
35
30
5
6
25
1
20
15
7
10
ppm
Br
4-Bromotoluene
2
3 5
1 140
131 ppm
4 130
120
110
100
90
80
70
60
50
40
30
20
10 ppm
Answers for Student Exercise 4.4 D-F
17
Br
Problem Problem 5.7D 4.4 D
3 5 4 2 2-Bromopentane
1
2
95
90
85
80
75
70
Problem 5.7E 4.4 E Problem
65 60 O 1
55
3
50
3 5 2 4 2-Hexanone
45
1
40
35
30
4
25
20
5
15
ppm
10
6
3
4 5
6
2
200
180
160
Problem Problem 5.7F 4.4 F
140 O
HO 1
120 2
100
80
60
40
ppm
20
3
Propionic Acid
3
2 1
180
160
140
120
100
80
60
40
20
ppm
Answers for Student Exercise 4.4 G-I Problem Problem 5.7G 4.4 G
2
H2N 1
18
4
3
Butylamine
1
95
90
85
80
75
70
65 1
Problem 5.7H 4.4 H Problem
60
55
2
OH
50
3
85
35
30
25
4
20
15
10
ppm
Note that it is often the case that the DEPT spectra are incorrect for alkynes. Intensities of the ≡CH are quite different than the ≡C−, which is apparent here.
2
90
40
3
3 Propargyl alcohol
1
95
45
2
80
75
70
Problem Problem 5.7I 4.4 I
65 -
O
60 O
55
N+ 1
2
50
45
40
35
30
25
20
15
10
ppm
10
ppm
3
1-Nitropropane
1
3
2
77.5 95
90
85
80
75
70
65
ppm
77.0 60
55
50
45
40
35
30
25
20
15
3
Answers for Student Exercise 4.4 J-L Problem Problem 5.7J 4.4 J
4
2 1
6
5
OH
19
O 2-Phenoxylethanol
3
2 4
5
6
1 170
160
150
140
130
120
110
100
6
90
Problem 5.7K 4.4 K Problem
1
O
60 ppm
70
3
2 5
80 4
Phenetole
3
2 4
6
5
1 160 150 140 130 120 110 100
90
80
70
60 O
O 1 2 3 5
Problem Problem 5.7L 4.4 L
50
40
30
20
ppm
4
Methyl Butyrate
3 4
2
5 1 170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
20
ppm
O
Answers for Student Exercise 4.4 M-O Problem Problem 5.7M 4.4 M
20
HN 1 2 6
5 4
3
Caprolactam
6
2 53
4
1 180
160
140
120
100
80
60
ppm
N
2
7
20
4
3
Problem 5.7N 4.4 N Problem
40 5
N
6 1 2-methylpyrazine
365 7 2 150
140
130
120
110
100
90
80
70
60
HO
Problem Problem 5.7O 4.4 O
O O
7
50 1
40
30
20
ppm
6
2
5
3 4 8 Methyl salicylate
7
170
1
160
5
34
130
120
6
8
2
150
140
110
100
90
80
70
60 ppm
21
Answers for Student Exercise 4.4 P-R Problem 5.7P 4.4 P Problem 3
O -
O
2 1
N+ 4
Cl
1-Chloro-4-Nitrobenzene
2
4
3
ppm
148 146 144
1
155 150 145 140 135 130 125 120 115 110 105 100
95
90
85
80
ppm
20
ppm
O
Problem Problem 5.7Q 4.4 Q
2
HO 1
4
3
6
5
7 Br
7-Bromo Heptanoic Acid
276453 1
180
160
140
120
Problem 5.7R 4.4 R Problem
100
HO 1
2
80 3
4
5-Hexyn-1-ol
40
5
Note that it is often the case that the DEPT spectra are incorrect for alkynes. Intensities of the ≡CH are quite different than the ≡C−, which is apparent here.
1
6
60
6
2
3
4
25
20
5
85
80
75
70
65
60
55
50
45
40
35
30
15
10
ppm
Answers for Student Exercise 4.4 S-U Problem Problem 5.7S 4.4 S
22
8
O
5 3 2 4 6 7 6-Methyl-5-hepten-2-one
1
7 4 5
3
8
1
6 2 200
180
160
140
120
100
80
60
40
20
ppm
O
Problem 5.7T 4.4 T Problem
2
HO 1
4
3
5
6
Hexanoic acid
2 4 35
6
1 180
160
140
120
100
HO
Problem Problem 5.7U 4.4 U
80 1
Cl
60
40
20
ppm
80
ppm
2 3
Cl
4 2,6-Dichlorophenol
3
4
4 2
1
121.2
155 150 145 140 135 130 125 120 115 110 105 100
ppm 95
90
85
Answers for Student Exercise 4.4 V-W
23
Problem Problem 5.7V 4.4 V HO
5 1
2 3
4 2,6-Dimethylphenol
3 5 1 150
2 140
130
4
120
110
100
90
80
70
60
50
40
ppm
30
20
6
45
O
Problem Problem 5.7W 4.4 W
1 6 5
4
2 3
2-Cyclohexen-1-one
3
2
1 200
180
160
140
120
100
80
60
40
20
ppm
Answers for Student Exercise 4.5 4.5
2nI +1 rule ID =1
1
24
Example
1
CDCl3
1
1
1
1
2
3
2
1
3
6
7
6
3
CD2Cl2 1
CD3Cl
Answers for Student Exercise 4.6 A-C
25
Problem 5.6A 4.6A Problem C5H10Br2
Br
2 Br 1 3 1,5-dibromopentane
1 2 3
75
70
65
60
55
50
45
40
35
30
Problem 5.6B 4.6B Problem C8H8O2
25
20
HO
15
10
5 ppm
O 7 1
2
6
8
3
5
4 2-methylbenzoic acid
4
6
3
5 8
7
2
1
132
170 160 150 140 130 120 110 100
Problem 5.6C 4.6C Problem C12H27N
1
2
3
4
130 90
128
80
70
60
50
4
2
40
30
20
ppm
H
5
6 N dihexylamine
6
75
70
ppm
65
60
55
50
5 3
45
40
35
30
25
1
20
15
10
5 ppm
Answers for Student Exercise 4.6 D-F Problem 5.6D 4.6D Problem C16H22O4
26 O
2
1
3
4 O 5
6
7
8
O O dibutyl phthalate
3 2
4
5
7
8
1
170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
20
ppm
7
Problem 5.6E 4.6E Problem C7H12O
1
2
4
3
6
5
O 5-methylhex-5-en-2-one
6
3 41 7
2 200
180
160
140
Problem 5.6F 4.6F Problem C8H14O
120
100
80
2
4 6 5 3 oct-3-yn-1-ol
7
4
80
20
ppm
8
6
1
85
40
OH 1
3
60
75
27 82
70
65
60
55
80
50
78
45
40
5
8
ppm
35
30
25
20
15
10
ppm
27
2 3 3
2
O 1
1
4 O 5 4 O 5
6 6
O ortho-diethyl phthalate There is one mirror image. There are 6 nonequivalent carbons, and there are 4 distinct proton signals, 2,3,5,6 with a integration ratio of 2:2:4:6, or 1:1:2:3.
DEPT 90
DEPT 135
Carbon - 13 4
180
160
1,3,2
140
6
5
120
100
PPM
80
60
40
20
0
28
O 7
O
4
6 O 51 2
1 5 O 6
7
2 3
meta-diethyl phthalate
There is one mirror image. There are 7 nonequivalent carbons, and there are 5 distinct proton signals, 2,3,4,5,6 with a integration ratio of 2:1:1:4:6..
DEPT 90
DEPT 135
Carbon - 13 21
5
7
6
4 3
180
160
140
120
100
PPM
80
60
40
20
0
29
5
4
O O
2
2 3
3 1
1 2
2
O
4
5
O
para-diethyl phthalate
There are two mirror images. There are 5 nonequivalent carbons, and there are 3 distinct proton signals, 2,4,5 with a integration ratio of 4:4:6, or 1:1:3.
DEPT 90
DEPT 135
Carbon - 13
2
3
180
160
140
5
4
1
120
100
PPM
80
60
40
20
0
Answers for Student Exercises 5.1 3.5
ppm
3.0
2.5
1 2.0
1.5
1.0
0.5
4
0.5 1.0
COSY
ppm
(a)
0.5 1.0
3
1.5
1.5 2
F1 2.0
2.0
2.5
2.5
3.0
3.0
4
3
2
Group # 1 2 3 4
δH 3.40 1.85 1.20 0.85
3.5
F2 HMQC
ppm 5
5
10
10
15
15
20
20
F1 25
25
30
30
35
35
40
40
45
45
3.0
2.8
2.6
2.4
2.2
2.0
F2
1.8
1.6
1.4
1.2
1.0
ppm
Br
(a) 1-bromobutane
1 3.5
1
δC 33.5 36.1 22.1 13.5
Answers for Student Exercises 5.1
2
1
ppm
3
2
HMBC
4
(a)
5 10
4
15
3
4
2
1 Br
(a) 1-bromobutane
20
3
F1 25 30
1 2
35
Group # 1 2 3 4
δH 3.40 1.85 1.20 0.85
δC 33.5 36.1 22.1 13.5
40 45 50 3.0
2.8
2.6
2.4
2.2 2
Hz
1
2.0
1.8
1.6
F2
1.4
1.2
ppm
1.0
3
INADEQUATE 4
Center Frequency
-3000
-3000
-2000
-2000
-1000
-1000
F1 0
0
1000
1000
2000
2000
3000
3000
45
40
35
30
F2
25
20
15
10
5
ppm
Answers for Student Exercises 5.1 ppm 6.0
5.5
5.0
4.5
4.0
3 3.5
3.0
2.5
2.0
1.5 5
1.5 9
2.0
4
6
COSY
ppm 5
1.5 2.0
6
4
1 3
2
(b) 7
O O 8
9
(b) (cyclohex-2-enyl)methyl acetate
2.5
2.5
1
3.0
3.0
F1 3.5
3.5 7
4.0
4.0
4.5
4.5
5.0
5.0 2
5.5
3
Group # 1 2 3 4 5 6 7 8 9
δH 2.80 5.59 5.59 1.96 1.65 1.80 4.05 NA 2.10
5.5
F2 HMQC
ppm 20
9
1
4
20
5 6
40
40
60
60 7 7
F1 80
80
100
100
120
120
2 3 6.0
5.5
5.0
4.5
4.0
3.5
F2
3.0
2.5
2.0
1.5
ppm
δC 36.0 131.5 125.5 29.8 27.0 33.4 67.5 170.5 20.7
Answers for Student Exercises 5.1 3 2
4 7
ppm
HMBC
9 46 5
1
5
56 9 41
40
6
4
1 3
2
(b) 7
O O 8
9
(b) (cyclohex-2-enyl)methyl acetate
7
60
Group # 1 2 3 4 5 6 7 8 9
80
F1
100
32
120 140
δH 2.80 5.59 5.59 1.96 1.65 1.80 4.05 NA 2.10
δC 36.0 131.5 125.5 29.8 27.0 33.4 67.5 170.5 20.7
160 8
180 6.0 Hz
5.5
5.0
4.5
4.0
3.0
2.5
2.0
1.5 ppm
F2 Center
Frequency
2 3
8
3.5
INADEQUATE 16 4 5 9
7
-10000
-10000
-5000
-5000
F1 0
0
5000
5000
10000
10000
180
160
140
120
100
F2
80
60
40
20
ppm
Answers for Student Exercises 5.1 ppm 7
6
5
1
3
2
4
O
2
1
7 6
4
5 3
1
9 8
ppm
COSY
(c)
10 1
OH
10
5
2
34 OH
Group # 1 2 3 4 5 6 7 8 9 10 OH
2
8 9
3
3
F1 4
4
5
5
δH NA 6.68 2.05 2.05 5.68 6.22 NA 2.65 3.20 1.05 0.5-4
5 6
6
6
2
F2 HMQC ppm
10
20
20 4
40
3 40
8 9
60
60
F1 80
80
100
100
120
5
6
140
120 140
2
7
6
5
4
3
F2
2
1
ppm
δC 143.2 150.0 28.3 30.7 122.1 131.1 206.7 45.5 60.5 8.9 NA
Answers for Student Exercises 5.1 2 6
6
5
4 3
8
9
HMBC
10
(c)
10
ppm 20
2
34 8
40
F1
Group # 10 3 4 8 9 5 6 1 2 7 OH
100 56 1 2
140 160 180 200
7
9 8
OH
10
5
80
120
1 6
4
9
60
3
O
δH 1.05 2.05 2.05 2.65 3.20 5.68 6.22 NA 6.68 NA 0.5-4
δC 8.9 28.3 30.7 45.5 60.5 122.1 131.1 143.2 150.0 206.7 NA
7 7
6
5
7
4 2 1
Hz
3
2
1
F2 Center 6
5 Frequency
ppm INADEQUATE 9
43
8
10
-10000
-10000
-5000
-5000
F1 0
0
5000
5000
10000
10000
15000
15000 200
180
160
140
120
F2
100
80
60
40
20
Hz
Answers for Student Exercises 5.1 ppm
2.5
2.0
7 1.5
1.0
0.5
COSY
ppm
(d) 0.5
0.5
5
4
3 2
1
5 1.0
1.0 4
1.5
F1
1.5
Group # 1 2 3 4 5
δH 1.80 NA 2.20 1.50 0.85
1 2.0
2.0
3
2.5
2.5
F2 HMQC ppm 5
10 20
F1
10
4
3
20
30
30
40
40
50
50
60
60
1
70
70
80
80
2.5
2.0
1.5
F2
1.0
0.5
ppm
δC 67.6 84.6 25.0 21.2 12.5
H
Answers for Student Exercises 5.1 1
3
ppm
8 4
HMBC
5
(d)
10
5
20
4
5
3 2
1
δH 1.80 NA 2.20 1.50 0.85
δC 67.6 84.6 25.0 21.2 12.5
H
4 3
30
Group # 1 2 3 4 5
F1 40 50 60 1
70 80
2 90 2.5 1
2.0 2
1.5
1.0
F2 Center
Frequency
0.5
ppm INADEQUATE 3 4
5
Hz
-4000
-4000
-2000
-2000
F1 0
0
2000
2000
4000
4000
6000
6000 90 85 80 75 70 65 60 55 50 45 40 35 30 25 20 15 10
F2
5
Hz
Answers for Student Exercises 5.1
9
ppm 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 6
1 5
2
(e)
O
1
1
1
2
3
2
3
3
F1 4
4
5
5 3
6
COSY
ppm
Group # 1 2 3 4 5 6
4
δH 1.86 NA 6.09 6.82 2.05 1.00
6
4
F2 HMQC ppm
6 5
20
F1
1
20
40
40
60
60
80
80
100
100
120
120
140
4
3 140
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
F2
ppm
5
δC 28.8 196.9 137.6 142.1 23.4 13.9
6
Answers for Student Exercises 5.1 ppm
4
10 5 1
3
HMBC
6 6 5 1
20 40 60
(e)
O 1
2
3
Group # 1 2 3 4 5 6
F1 80 100 120
4 δH 1.86 NA 6.09 6.82 2.05 1.00
5
6
δC 28.8 196.9 137.6 142.1 23.4 13.9
3 4
140 160 180
2
200 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 4 3
2
ppm
INADEQUATE
F2 Center
Frequency
15
Hz
6
-10000
-10000
-5000
-5000
F1 0
0
5000
5000
10000
10000
15000 200
180
160
140
120
F2
100
80
60
40
20
15000 Hz
Answers for Student Exercises 5.1
11
ppm 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 5
1 4
2
1 1
2
1
3
ppm
O 2
Group # 1 2 3 4 5
3
F1 4
COSY
(f) 4
3 δH 3.20 6.14 4.63 2.05 1.00
4 3
5
5 2
6
6
F2 HMQC ppm
5 4
20 40
20 40
1
F1
60
60
80
80 3
100
100
120 140
120 2
140
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
F2
ppm
δC 55.8 143.5 102.0 23.1 13.6
5
Answers for Student Exercises 5.1 2
12 3
ppm
HMBC
5
4
1
(f) 5
20
1
O 2
4
4
5
3
40 Group # 1 2 3 4 5
1
F1 60 80 100
δH 3.20 6.14 4.63 2.05 1.00
δC 55.8 143.5 102.0 23.1 13.6
3
120 140
2 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5
ppm INADEQUATE
F2 Center 2
Hz
Frequency
3
4
1
5
-5000
-5000
F1 0
0
5000
5000
10000
10000
150 140 130 120 110 100
90
80
F2
70
60
50
40
30
20
10
Hz
Answers for Student Exercises 5.1
13
ppm 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 5
1
ppm 1 1
2
3
F1 3
4
4
5
6
5 NH
6
F2 HMQC ppm
5
20
1
4
40 60
F1
20 40 60
3
80
80
100
100
120
120
140
140 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
F2
(g) 4
δH δC Group # 1 2.95 28.4 2 NA 157.8 3 4.10 63.0 4 1.60 20.7 5 0.85 13.0 NH 4.5-7.5 NA
1 3
O N 2 O 3 H
4 2
COSY
ppm
5
Answers for Student Exercises 5.1
14 3
1
4
ppm
HMBC
5 5
20
4
1
F1
1
4
5
δH δC Group # 1 2.95 28.4 2 NA 157.8 3 4.10 63.0 4 1.60 20.7 5 0.85 13.0 NH 4.5-7.5 NA
80 100
(g)
N 2 O 3 H
40 60
O
3
120 140
2 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5
ppm
F2 Center
Frequency 3
2
INADEQUATE 1
4 5
Hz -10000
-10000
-5000
-5000
F1 0
0
5000
5000
10000
10000 140
120
100
F2
80
60
40
20
Hz
Answers for Student Exercises 5.1 ppm 6.0
5.5
5.0
4.5
4.0
15 3.5
3.0
2.5
2.0
1.5
1.0
ppm
1
1.0
1.0
1
1.5
1.5
2.0
2.0
2.5
2.5
F1 3.0
3.0
3.5
COSY
2 O 3 O
(h) Group # 1 2 3
δH 1.20 3.40 4.95
3.5
2
4.0
4.0
4.5
4.5
3
5.0
5.0
5.5
5.5
F2 HMQC
ppm
F1
1
20
20
40
40 2
60
60
80
80
100
100 3
120
120 6.0
5.5
5.0
4.5
4.0
3.5
F2
3.0
2.5
2.0
1.5
1.0
ppm
δC 11.6 61.0 113.3
Answers for Student Exercises 5.1 3
16 2
HMBC
1
ppm 1
1
20
(h)
40
F1
2 O 3 O
60
Group # 1 2 3
2
δH 1.20 3.40 4.95
δC 11.6 61.0 113.3
80
100 3 120 6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
ppm
1.5
INADEQUATE
F2 Center
Frequency 2
3 Hz
1
-8000
-8000
-6000
-6000
-4000
-4000
-2000
-2000
F1 0
0
2000
2000
4000
4000
6000
6000
8000
8000 120
110
100
90
80
70
F2
60
50
40
30
20
10
Hz
Answers for Student Exercises 5.1 ppm 2.0
1.8
1.6
17
1.4
1.2
1.0
0.8
0.6
0.6
0.6 5
0.8
0.8
1.0
1.0
F1 1.2
4
6
1.4
1.2
1
1.4
3
1.6
COSY
ppm
(i)
6
1
HO
2
3
δH Group # 1 1.20 2 NA 3 1.50 4 1.20 5 0.85 6 1.20 OH 0.5-4.0
1.6 OH
1.8
1.8
F2 HMQC
ppm 10
10
5
4
20
20 6 1
30
F1 40
30 40
3
50
50
60
60
70
70
80
80 ppm
2.0
1.8
1.6
1.4
1.2
F2
1.0
0.8
0.6
5
4 δC 29.8 68.3 46.7 15.1 14.1 29.8 NA
Answers for Student Exercises 5.1
18 6 4 1
3
HMBC
5
ppm 10
4
5
20
F1
6
1
HO 16
30 40
3 50
(i)
2
3
5
4
δH Group # 1 1.20 2 NA 3 1.50 4 1.20 5 0.85 6 1.20 OH 0.5-4.0
δC 29.8 68.3 46.7 15.1 14.1 29.8 NA
60 2
70
2.0
1.8
1.6
1.4
1.2
1.0
ppm
0.8
F2 Center
3 Frequency
2 Hz
INADEQUATE 45
1,6
-4000
-4000
-2000
-2000
F1 0
0
2000
2000
4000
4000
6000 75
70
65
60
55
50
45
F2
40
35
30
25
20
15
10
5
6000 Hz
Answers for Student Exercises 5.1 ppm 3.0
2.8
2.6
2.4
19
2.2
2.0
1.8
1.6
1.4
1.2
ppm
COSY
(j) 1.2
1.2 1
1.4
1.4 3
1.6
F1
1.6
1.8
1.8
2.0
Group # 1 2 3
S
3 δH 2.10 2.60 1.60
2.0
1
2.2
2.2
2.4
2.4 2
2.6
S 2
2.6
2.8
2.8
F2 HMQC ppm 15
15 1
20
20
F1 25
25 3
30
30 2
35
35
40
40 ppm
3.0
2.8
2.6
2.4
2.2
2.0
F2
1.8
1.6
1.4
1.2
δC 17.5 33.5 29.6
Answers for Student Exercises 5.1
20 1
2
HMBC
3
ppm
(j) 1
S 2
15 1 20
F1
Group # 1 2 3
S
3 δH 2.10 2.60 1.60
δC 17.5 33.5 29.6
25 3
30
2 35
40 3.0
2.8
2.6
2.4
2.2
2
3
2.0
1.8
1.6
ppm
1.4
F2 Center
Frequency
INADEQUATE
1
Hz -1500
-1500
-1000
-1000
-500
-500
F1 0
0
500
500
3 to 3'
1000
1000
1500
1500
2000
2000 40
38
36
34
32
30
28
26
F2
24
22
20
18
16
14
12
Hz
Answers for Student Exercises 5.1
21
ppm 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5
COSY
ppm
(k)
8
1
6,7 3
3
4 8
4
4
5
5
6
6
5 2
δH NA 7.80 7.25 NA NA 2.95 2.95 2.25
7
3 2
F2 HMQC ppm
8
40
40
6,7
60
60
80
80
100
100
120
120
F1
2 3.0
3 2.8
2.6
2.4
2.2
2.0
F2
1.8
1.6
1.4
1.2
ppm
6
N 7
3 Group # 1 2 3 4 5 6 7 8
F1
7
O
δC 130.6 127.2 129.2 141.2 171.0 38.5 38.5 21.3
Answers for Student Exercises 5.1 2
22 7 6
3
HMBC
8
ppm
(k)
8
1
67
40
4 8
60
F1 80
23 1 4
140
6
5
N
2
7
3 Group # 1 2 3 4 5 6 7 8
100 120
O
δH NA 7.80 7.25 NA NA 2.95 2.95 2.25
δC 130.6 127.2 129.2 141.2 171.0 38.5 38.5 21.3
160 5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 5
4
Hz
ppm
F2 Center
Frequency
13 2
INADEQUATE 7 6
8
-10000
-10000
-5000
-5000
F1 0
0
5000
5000
10000
10000
160
140
120
100
F2
80
60
40
20
Hz
Answers for Student Exercises 5.1
23
ppm 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5
COSY
ppm
O
(l)
6
3
5
3
2 3
4
5
5
6
6
7
5
4
3 7
6
F2 HMQC ppm 8 40
40
60
60
80
80
100
100
F1
3
5
120
6
3.0
120 4
2.8
2.6
2.4
2.2
2.0
F2
1.8
1.6
1.4
1.2
OH
δH Group # 1 NA 2 NA 3 6.85 4 7.05 5 7.25 6 7.70 7 NA 8 2.40 OH 5.5-12.5
F1
ppm
8
7
4 4
1
δC 123.6 154.7 115.4 132.9 120.8 129.7 197.6 26.3 NA
Answers for Student Exercises 5.1 6
24
54 3
HMBC
8
ppm
8
40
(l) 6 5
60
3
3 51 64
140
2
160
8
2
80
120
1 7
4
F1 100
O
OH
δH Group # 1 NA 2 NA 3 6.85 4 7.05 5 7.25 6 7.70 7 NA 8 2.40 OH 5.5-12.5
δC 123.6 154.7 115.4 132.9 120.8 129.7 197.6 26.3 NA
180 7 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0
ppm
INADEQUATE
F2
7
Center 4 6 1 5 3 Frequency
2
8
Hz -10000
-10000
-5000
-5000
F1 0
0
5000
5000
10000
10000
180
160
140
120
F2
100
80
60
40
Hz
Answers for Student Exercises 5.1 ppm 11
10
9
25 8
7
6
5
ppm
COSY
(m) 1
5
5
Cl
1
2 H
O 6
6
F1 7
7
8
8
9
Group # 1 2
δH 4.95 9.80
9 2
10
10
F2 HMQC
ppm 1
60
60
80
80
100
100
F1 120
120
140
140
160
160
180
180 2
200 11
200 10
9
8
7
F2
6
5
ppm
δC 59.5 199.7
Answers for Student Exercises 5.1
26 HMBC
1
2 ppm 60
1
(m)
Cl
1
80
2 H
O
100
Group # 1 2
F1
120
δH 4.95 9.80
δC 59.5 199.7
140 160 180 2
200 11
10
9
8
7
6
5
F2 Center
Frequency
2
ppm
INADEQUATE
1
Hz -10000
-10000
-5000
-5000
F1 0
0
5000
5000
10000
10000
200
180
160
140
F2
120
100
80
60
Hz
Answers for Student Exercises 5.1 ppm 8.0
7.5
7.0
6.5
27 6.0
5.5
5.0
4.5
ppm
(n)
1trans
4.5
COSY
1cis
4.5
H
1cis
5.0
5.0
5.5
5.5
6.0
6.0
6.5
6.5
F1
H
H 1trans Group # 1cis 1trans 2
2
F δH 4.85 4.23 6.79
2
7.0
7.0
7.5
7.5
F2 HMQC
ppm 1
130
130
140
140
150
150
F1 160
160
170
170
180
180 2
190
190
200 8.0
7.5
7.0
6.5
6.0
F2
5.5
5.0
4.5
200 ppm
δC 132.2 132.2 191.2
Answers for Student Exercises 5.1
28 1cis
2
HMBC
1trans
ppm
(n)
130
H
1
140
H 1trans
150
F1
Group # 1cis 1trans 2
160 170
1cis
H
2
F δH 4.85 4.23 6.79
δC 132.2 132.2 191.2
180 190
2 7.0
6.5
6.0 2
5.5
5.0
4.5
F2 Center
Frequency
ppm
INADEQUATE
1
Hz -4000
-4000
-2000
-2000
F1 0
0
2000
2000
4000
4000
6000
6000 Hz
190
180
170
F2
160
150
140
130
Answers for Student Exercises 5.1 ppm 6.0
5.5
5.0
4.5
4.0
29 3.5
3.0
2.5
2.0
1.5 33' 4
1.5
F1
1.5
22' 6
2.0
3'
2'
2.5
3.0
3.0
3.5
3.5
4.0
4.0
4.5
4.5 1
2
Group # 1 2,2' 3,3' 4 5 6
δH 4.95 1.60 1.44 1.44 NA 2.00
5.5
F2 HMQC
ppm
33' 4
6 22'
40 60
40 60
1
F1
80
80
100
100
120
120
140
140
160
160
6.0
5.5
5.0
4.5
4.0
3.5
F2
3.0
2.5
2.0
1.5
ppm
O
5 6
3
5.0
5.5
(o)
O
1
2.0 4
2.5
5.0
COSY
ppm
δC 77.9 32.9 23.9 26.9 168.0 20.8
Answers for Student Exercises 5.1
30 6
1
ppm
33' 22' 4
HMBC 6 3 3' 4 2
40
2'
(o)
O
5
2
4 60
O
1
6
3 1
F1 80
Group # 1 2,2' 3,3' 4 5 6
100 120
δH 4.95 1.60 1.44 1.44 NA 2.00
δC 77.9 32.9 23.9 26.9 168.0 20.8
140 160
5 6.0
5.5
5.0
4.5
4.0
3.5
3.0
F2
Center Frequency 1
5
2.5
2.0
ppm INADEQUATE 2 43 6
Hz -10000
-10000
-5000
-5000
F1 0
0
5000
5000
10000
10000
160
140
120
100
F2
80
60
40
20
Hz
Answers for Student Exercises 5.2
31
CH2 H
g= geminal v= vicinal lr= long range
5 4
HO
7
7 8 CH2
3
H3C
8
6
2
1 CH3
CH3 1
CH2=
4
5 5'
OH 2
3 3'
ppm 0.5
v 1.0
v
v
1.5
g v
v
2.0
lr
2.5
v
g
3.0
F1
3.5
v
4.0
v
4.5 5.0
g
v
lr
5.5 6.0 6.5
v
7.0 7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
F2
3.0
2.5
2.0
1.5
1.0
0.5
ppm
Answers for Student Exercises 5.2
32
CH2 H
5
6
4
HO
8 CH2
3
H3C
7
2
CH3 1
Carbon 13 Signals 1
2
3
1
Bonded
α
β
2
α
Bonded
α
β
S
3
β
α
Bonded
α
β
I
4
β
α
Bonded
α
β
g
5
β
α
Bonded
α
β
n
6
l
7
β
α
Bonded
α
a
8
β
α
Bonded
l
CH3
s
CH2=
1
H
β
α
4
5
6
7
8
CH3
CH2=
β α β
β
β β Bonded
β
α
β
Bonded
Answers for Student Exercises 5.4 1
33
H NMR 600 MHz
4
5’ 3
5
1300
6
2
Hz 1250
Hz
4’
Hz
1150
3’ 6
1000 Hz
1050
2.3 13
2.2
2.1
860 840 820 Hz
2.0
1.9
1.8
1.7
620 600 580 Hz
1.6
1.5
1.4
1.3
1.2
ppm
1.1
1.0
5
3 4
C/DEPT 600 MHz
O 6
1 2 5 3 4
6
2
2-methylcyclopentanone
1
220
200
180
160
140
120
100
80
60
40
20
ppm
Answers for Student Exercises 5.4 ppm
COSY 600 MHz
1.0
1.0
6
1.2
1.2
1.4
1.4
ppm 2.4
F1
34
2.2
2.0
1.8
1.6
1.4
1.2
1.0
1.6
O
3’
6
1 2 5 3 4
1.6
4’ 1.8
1.8
2.0
2.0
2.2
2.2
4
5 3 2 5’
ppm
F2
4
4’
5’ 2
3 5
HMQC 600 MHz
6
3’
2-methylcyclopentanone
6 15
15
20
20
25
25
F1 30
30
35
35
40
40
45
45
2.4
2.2
2.0
1.8
1.6
F2
1.4
1.2
1.0
ppm
4
3
5
2
Answers for Student Exercises 5.5 1
35
H NMR 600 MHz 7
9
4750 Hz
4800
8
4400 Hz
4450
2
3
1700 Hz 1550
9
4300 Hz
4350
4
1750
6
1500 Hz
2
1200 Hz
1250
4 3
7 8 6 O 9
10
8 7
5
6
8.0 13
7.5
7.0
6.5
6.0
5.5
1
2 3
4
5.0
4.5
4.0
3.5
3.0
2.0 ppm
2.5
C/DEPT 600 MHz
8 6 97
5
1
200
180
160
140
2
4
3
10
120
100
80
60
40
ppm
Answers for Student Exercises 5.5 ppm
8
7
6
36 5
4
3
2
2
COSY 600 MHz
2
3
3
8.0
4
7.5
7.0 ppm
5
O
4
7.0
10
1
2
8
7
5
7 6
5
3 4
6
9
8.0
9 8
6
7.5
6
4
2
3 ppm
F1
ppm
7
7
8
8
F2
HMQC 600 MHz
ppm
3
4
40
60
40
ppm 125
7 9 6
130
F1
80
60
80
8
135 8.2 8.0 7.8 7.6 7.4 7.2
ppm
100
100
120
120
140
140 9
8
7
6
5
F2
4
3
2
ppm
2
Answers for Student Exercises 5.6 1
H NMR 600 MHz
Hz
5470 4
5200
Hz
5190
2590
8
8
Hz
2580
790
7
3
1
5
3
4
2
5
6
Hz
780
O
4
4900 Hz
4910
7
4360 Hz
4370
3
5
1
5480
37
O
CH2
7
8 CH3
1
N
ethyl nicotinate
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
ppm
13 13C/DEPT
MHz C/DEPT600 NMR 150.9 MHz
5
1
7
4
3
8 2
6
160
150
140
130
120
110
100
90
80
70
60
50
40
30
ppm
Answers for Student Exercises 5.6
ppm
9
7
6
5
4
3
2
ppm
2
3 4
2
5
6
O
CH2
7
8 CH3
3
1
N
4
4
ethyl nicotinate
F1 5
5
6
6
7
7
8
8
9
9
ppm
F1
1
COSY 600 MHz 8
O
2 3
8
38
5 3
F2
4
7
4 3 5 1
8
7
HMQC 600 MHz
20
20
40
40
60
60
80
80
100
100
120
120
8
7
2
140
140
4 3 1
160
160 9
8
7
6
5
F2
4
3
2
ppm
6
5
Answers for Student Exercises 5.6
39 INADEQUATE 600 MHz INADEQUATE 150.9 MHz
Hz -25000
7
O
3
-20000 -15000
4
2
5
1
N
-10000
6
O
-25000
8
-20000
8
CH2
7
CH3
-15000 -10000
ethyl nicotinate
-5000
F1
-5000
0
0
5000
5000
10000
10000
15000
15000
20000
20000
25000
25000 160
140
120
5 Hz
6
100
1
80
60
F2
40
3
ppm
20
2
4
12000
12000
13000
13000
F1
14000
14000
15000
15000
16000
16000
17000
17000
165
160
155
150
145
F2
140
135
130
125
ppm
Answers for Student Exercises 5.7 8
INADEQUATE 150.9 MHz
13
40
Hz -10000
-10000 15 H3C
-5000
H3C 14
CH3 12
4
1
11
5 9
10
-5000
O 6
8
H
F1
3
2
H
7
CH2 13
0
0
8-7 8-9
5000
5000 8-13
10000
10000 160 150 140 130 120 110 100 5
90
1 9
4
80
70
60 50 14 11 67 2
10 3
40
30 15
ppm
20 12
Hz -9000
-9000
11-15 11-14
3-2
-8000
C6-C7
-8000
10-11
4-12
F1-7000
-7000
1-2 1-11 5-6
-6000
9-10
-6000
4-3
-5000
-5000
1-9
-4000
-4000 5-4
65
60
55
50
45
F2
40
35
30
25
20
15
ppm
Answers for Student Exercises 5.7
41
The following correlations can be found in the INADEQUATE spectrum of caryophyllene oxide Carbon 1 correlates with carbons 2, 9, and 11 Carbon 2 correlates with carbons 1 and 3 Carbon 3 correlates with carbons 2 and 4 Carbon 4 correlates with carbons 3, 4, and 12 Carbon 5 correlates with carbons 4, and 6 Carbon 6 correlates with carbons 5, and 7 Carbon 7 correlates with carbons 6, and 8 Carbon 8 correlates with carbons 7, 9, and 13 Carbon 9 correlates with carbons 1, 8, and 10 Carbon 10 correlates with carbons 9 and 11 Carbon 11 correlates with carbons 1, 10, 14, and 15 Carbon 12 correlates with carbons 4 Carbon 13 correlates with carbons 8 Carbon 14 correlates with carbons 11 Carbon 15 correlates with carbons 11
15 H3C H3C 14
3
2
H
CH3 12
4
1
11
5 9
10
6 8
H CH2 13
O
7
Answers for Student Exercises 5.8 1
42
H NMR 600 MHz 2
1
1’ 6
3500
Hz
3450
3050
5
8
OH
3000
Hz
1400
9
Hz
1350
10
9
10
4
1200
Hz
1150
950
8
Hz 9 750
900
Hz
700
OH
1
2
6
1’
4 5
3
2
5
4
1
6
OH
7 8 10 3,7-dimethylocta-1,6-dien-3-ol
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
ppm
1.5
13 13 C/DEPT
NMR 150.9 MHz C/DEPT 600 MHz
1 6
2
140
130
5
8
7
150
9
4
3
120
110
100
90
80
10
70
60
50
40
30
20 ppm
Answers for Student Exercises 5.8 ppm 6.0 5.5 5.0 4.5 4.0 3.5
43 3.0
2.5
2.0
1.5
ppm
COSY 600 MHz 9
1.5
1.5
2.0
2.0 9
2.5 3.0
F1
3
4 5
3.5 4.0
2.5
OH
6
2
8
10
5 OH
3.0
1
3.5 4.0
7 8 10 3,7-dimethylocta-1,6-dien-3-ol
4.5
4
4.5
5.0
5.0
5.5
5.5
1’ 6 1 2
2
ppm
F2
1,6,1’
8 10 4 5
HMQC 600 MHz
9
20
20
40
40
60
60
10
5
4
3
F1
80
80
100
100
1 120
120
6 7
140
140
6.0
5.5
5.0
4.5
4.0
3.5
F2
3.0
2.5
2.0
1.5
ppm
8 9
2
HMBC 600 MHz
Answers for Student Exercises 5.8
8
161
2
OH
ppm 20 4 5
44
9
4 10
9
40
5
10
5 8 9
OH
3
2
4
1
6
60
F1
3
7 8 10 3,7-dimethylocta-1,6-dien-3-ol
80
100
1 120
6 7
140
2
160 6.0
5.5
5.0
4.5
4.0 F2 3.5
3.0
2.5
2.0
ppm
1.5 ppm
20
20
40
40
60
60
F1
ppm
ppm
120
120
140
140 6.0
5.9
5.8
ppm
5.2
5.0
F2
ppm
2.0
1.5
ppm
ppm
Answers for Student Exercises 5.8 2
6
45 1
INADEQUATE 150.9 INADEQUATE 600MHz MHz
3
4
7
9 85 10
Hz 9 4
-15000
-10000
5
OH
3 6
2
-15000
1
7 8 10 3,7-dimethylocta-1,6-dien-3-ol
-10000
-5000
-5000
F1 0
0
5000
5000
10000
10000
15000
15000
140
120
100
80
F2
60
40
20
ppm
Answers for Student Exercises 5.9
ppm
5.2 5.0 4.8 4.6 4.4 4.2 4.0
F1
3.6
α2 α4
β5 β3 β4
3.8
α3 α6 α5
β6’
TOCSY 600 MHz
3.8 3.6 3.4
β2
3.4
4.0
46
3.4 G2
3.6
G3 G5 G6
3.8
G4
β6
4.0
4.2
4.2
4.4
4.4
4.6
4.6
4.8
4.8
5.0
5.0
5.2
5.2 5.2 5.0 4.8 4.6 4.4 4.2 4.0
3.8 3.6 3.4
G1 β1
HDO α1
ppm
F1 Correlations from the three anomeric protons are drawn. These correlations show the ring protons for the three monosaccharide residues of lactose. Correlations among the ring protons are difficult to decipher due to overlap. Results from the 1D HOHAHA in Figure 5.26 agree with these findings.
Answers for Student Exercises 5.10 1
47
H NMR 600 6MHz CH2OH O H HO CH2OH 5 H 4 O H H 1 HO HO H HHO 3 H 2 H HO H
H
HO
6 CH52 H HO 4 H HO HO 3 H HO
α-Galactose Ring A
C3
1
CH2
O H O H
H
O H
H1
H
O
3.9
O
3
HO
4
3.7
CH2OH
β-Fructose Ring C
C1
B2 B4
3.6
ppm
3.5
C3
A1
6
H
A6 C1 A2 B3 C6 C6’ B6’
3.8
CH2OH
H
HO
HO
5H
HO
HO
HDO B1
H
O
H
O
α-Glucose Ring B
4.0
CH2OH
2 CH2HOH
H2 HO
C4 B5 B6 A4 A5 C5 A3
4.1
O
C4
5.4 5.3 5.2 5.1 5.0 4.9 4.8 4.7 4.6 4.5 4.4 4.3 4.2 4.1 4.0 3.9 3.8 3.7 3.6
ppm
13 13C/DEPT
150.9 MHz C/DEPT NMR 600 MHz
74.0
B5
B3
C3
73.5
73.0
100
72.0
71.5
95
71.0
C5
B1
A1
C2
72.5
A5 B2
90
85
A3 B4 A4
70.5
70.0
69.5
C3 C4
80
75
A2
69.0
C6 C1A6
B6
70
ppm
65
ppm
Answers for Student Exercises 5.10
48
Mixing time 300 ms 5.40 ppm irradiated
1-d TOCSY 600 MHz
B6
B6’
Mixing time 80 ms B5
B4
Mixing time 40 ms B3 B2
Mixing time 20 ms
4.05
4.00
3.95
3.90
3.85
3.80
3.75
3.70
3.65
3.60
Mixing time 300 ms 4.97 ppm irradiated
A5
3.55
3.50
ppm
1-d TOCSY 600 MHz
A6
Mixing time 80 ms A4 A3
Mixing time 40 ms
Mixing time 20 ms
A2
1
4.05
4.00
3.95
3.90
3.85
3.80
3.75
3.70
3.65
3.60
H NMR 600 MHz
3.55
3.50
ppm
Answers for Student Exercises 5.10
49
Mixing time 80 ms
1-d TOCSY 600 MHz C6 C6’
Mixing time 40 ms C5
Mixing time 20 ms C4
1
4.05
4.00
3.95
3.90
3.85
6 CH2OH HO
4
H HO
H H
5
O
1
3
HO
2
O H
3.70
4
1
CH2 H HO
HO
H
α-Galactose Ring A
3.75
3.65
3.60
3.55
3.50
6
H
H
3.80
H NMR 600 MHz
5
O
H
3
2 HO
α-Glucose Ring B
2
1
H
CH2OH H
O
HO
3 HO
H
O
4 H
β-Fructose Ring C
5 CH2OH
6
ppm
Answers for Student Exercises 5.10 ppm
F1
5.4 5.2 5.0 4.8 4.6
50 4.4 4.2 4.0 3.8 3.6
COSY 600 MHz
ppm
3.6
3.6
3.8
3.8
4.0
4.0
4.2
4.2
4.4
4.4
4.6
4.6
4.8
4.8
5.0
5.0
5.2
5.2
5.4
5.4
C3
HDO A1
B1
COSY 600 MHz
ppm
B4 B2
3.5 3.6
C1
B6’ 3.7
F1
C6’B3 C6 A2 C5 A3 A5 A4 B6 B5 C4
3.8 3.9 4.0 4.1
C3
4.2 4.2
4.1
4.0
3.9
3.8
F2
3.7
3.6
3.5
ppm
A6
Answers for Student Exercises 5.10 ppm 5.4 5.2 5.0 4.8 4.6 4.4 4.2 4.0 3.8 3.6
F1
ppm
3.6
3.6
3.8
3.8
4.0
4.0
4.2
4.2
4.4
4.4
4.6
4.6
4.8
4.8
5.0
5.0
5.2
5.2
5.4
5.4
51
TOCSY 600 MHz
C3
HDO A1
B1
TOCSY 600 MHz
ppm
B4 B2
3.5 3.6
C1
B6’ 3.7
F1
C6’B3 C6 A2 C5 A3 A5 A4 B6 B5 C4
3.8 3.9 4.0 4.1
C3
4.2 4.2
4.1
4.0
3.9
3.8
F2
3.7
3.6
3.5
ppm
A6
Answers for Student Exercises 5.10 B1 A1 C1 B5A4 A6 C3 C4 B6 C6 C6’ A5 A3C5 A2 B3 B6’ ppm 5.5
ppm
4.1
4.0
3.9
3.8
3.7
3.6
52
HMQC 600 MHz B2 B4 3.5
ppm
60
A6 C1 C6
F1 65
B6
ppm
A2 A4 B4 A3
69 70
B2 A5 B5
71 72
B3
73
C4
74
F1
75 76
C3
77 78 79 80 81
C5
ppm
B1
95
F1
A1
100
C2
105 5.5
ppm
4.1
4.0
F2
3.9
3.8
3.7
3.6
3.5
ppm
Answers for Student Exercises 5.10 B1
HMQC-TOCSY 600 MHz C1 B5A4 A6 C4 B6 C6 C6’ A5 A3C5 A2 B3 B6’ B2 B4
A1 C3
ppm 5.5
ppm
53
4.1
4.0
3.9
3.8
3.7
3.6
3.5
ppm
60
A6 C1 C6
F1 65
B6
ppm
A2 A4 B4 A3
69 70
B2A5 B5
71 72
B3
73
C4
74
F1
75 76
C3 77 78 79 80 81
C5
ppm
B1
95
F1
A1
100
C2
105 5.5
ppm
4.1
4.0
F2
3.9
3.8
3.7
3.6
3.5
ppm
Answers for Student Exercises 5.10 B1 A1 C1 B5A4 A6 C3 C4 B6 C6 C6’ A5 A3C5 A2 B3 B6’ ppm 5.5
ppm
4.1
4.0
3.9
3.8
3.7
3.6
54
HMBC 600 MHz B2 B4 3.5
ppm
60
A6 C1 C6
F1 65
B6
ppm
A2 A4 B4 A3
69 70
B2A5 B5
71 72
B3
73
C4
74
F1
75 76
C3
77 78 79 80 81
C5
ppm
B1
95
F1
A1
100
C2
105 5.5
ppm
4.1
4.0
F2
3.9
3.8
3.7
3.6
3.5
ppm
Answers for Student Exercises 5.11 1
55
H NMR 600 MHz 22
6
23
Hz
3200 7’,8,24,25 3100 2’ 11
15
1000
2200
4
Hz
1’
14
HO HO
3
10
4
600 Hz
6
CH3
CH3 18 20 CHCH 3 3
13
15
7
1
Hz
1100
29 27 26
18
500
Hz
29
16
1000 Hz
28 23
24
H
27 25 26
16
HH
7
4.5
600
22
17
14
8
5
5.0
12
9
21 9
700
19 11 CH 33 H 1 CH
1300
19
21
2
20
Hz
2100 17 15’
28 16’ 12’
28
900
12
3
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
13 13
C/DEPT600 NMR 150.9 MHz C/DEPT MHz
21
8 25
22
23
6
130
120
7 32.0
27
29
11
2 ppm
3
ppm
21.5
5
140
110
100
90
80
70
18
13 20 12 1417 9 24 4 15 1 16 28 10 19 26
60
50
40
30
20 ppm
Answers for Student Exercises 5.11
56
ppm 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
COSY 600 MHz
ppm
18
1
1
2
2
19
4 29
21
311
19
2
HO
1 CH3
3
10
4
6
CH3 20
13
9 8
5
CH3
7
28
22
12 18
17
14 15
4
23
3
27
24
25 26
4
16
2
3
2’
4
20
24
4 7
7’
5
23 22 6
5
COSY 600 MHz
ppm 0.6 0.8 9 14
1.0 29 to 28’
1.2 29 to 28
1.4
F1
1.6
27 26 to 25 15 7’
1.8
16
17
2
15’
15 to 14
1’ 8
2.0
7’,11
2.2
7 2lr
7’
17
1’ 15’ 28’ 17 12’ 16
2.2
2.0
1.8
1.6
1.4
21 7 12 20
21
4
F2
1.27 1.0
0.8 7’ 0.6
21
28 2 11 7’ 8 24 25 15 16
2.4 2.4
18 26 27
ppm
17
29
19
Answers for Student Exercises 5.11 6
22
3
23
4 ppm 5.5
ppm
3.6
ppm
57
8 29 25 21 HMQC 600 MHz 7’11 1927 26 242 12’ 28’15’ 14 2 18 12 1 16 15 28 16’ 17 1 9 20 7
2.2
2.0
1.8
1.6
1.4
1.2
1.0
0.8
0.6
ppm
18
29
15
26 19 27 2111 15 28
20 25
16 2
30 35
725 8
10
F1
1 12 20 13 4
40 45 50
9 24
55
17 14
60 65
29
21 19
70 3
HO
11
1 CH3
2
10
4
CH3 20
23
17
14
8
5
ppm
12 18 13
9
28
22
CH3
15
24
27
3
25 26
16
6
7
6
23
130
22
140
5 5.5
ppm
3.6
ppm
2.2
2.0
F2
1.8
1.6
1.4
1.2
1.0
0.8
0.6
ppm
Answers for Student Exercises 5.11 22
6
3
23
4 ppm 5.5
ppm
3.6
ppm
2.2
2.0
1.8
1.6
1.4
1.2
12-18
15 23-26 6-19 22,23-21
0.8
0.6
ppm
18
14-18
29
28’-29
13C Satellite peaks
24 25-26
26 19
27-26
1
1’9
2711 21 15 28
28’ 12-11
22,23-28
25
1.0
17-18 24-29 28-29
20
24+25-27
9-11 14-15
16-15 24 25-28
26-27
29-28 17 15 14-16
30
6-7 22,23-25
3-2
4-2
7-8
1-2 15-8
12’-8 6-10 3-1
F1
4-10
1,2-10
8,7’,-10
2-1
22,23-20
40
2’-1 11-12
3-4 12-13
6-4
45 50
22,23-24
55
22,23-17
2-4
7-14
1 CH3
HO
3
10
4
8
5 6
6-3 4-3
CH3
CH3 20
27,29,26-24
15
17 14
18-17 18-14
29
28
22 23
27
24
17
14
9 24
21
16’ 12 15-14
12 18 13
9
28’-24 16’ 12
21
11
18-13
12’ 1-9 19-9
15 8-14 19
1 12 20 13 4
9-1 21-20 18-12
17-12 16-20 17-20
25-24 28-24
2
10
9-10
19
16-17
60
70
1’19
7’,8,11
25 26
16
7
1,2 -3
725 8
27 26-25
16-13 15,11-13 12’,15’,17-13 14-13
12-9, and 7-9
65
16 2
24,28-25 28’-25 15’-8 14,9-(7,8)
.
35
58
8 25 21 HMBC 600 MHz 7’11 19272926 242 12’ 28’15’ 14 2 18 12 1 16 15 28 16’ 17 1’ 9 20 7
3 2’-3
1’-3
ppm
6 4-6
22-23
130
7-6 1-6(4b) 20-23 20-22
140
6-5
24,25 28-23 24-22
23
28’-23 27 26-23(4b) 17-22 21-22
22
3-5 4-5
5.5
7’-6
ppm
3.6
ppm
2.2
7-5
2.0
F2
1-5
1.8
7’-5
1.6
5
19-5
1.4
1.2
1.0
0.8
0.6
ppm
Answers for Student Exercises 5.11
59
1
H NMR 600 MHz 0o C in 5%/95% D2O/H2O
KNH
T2
SNH
S3
T3 K2 S2
5400
5300
5200
Hz
5100
2700
2600
T4
K6
K3 K3’
2500
Hz
2400
T4
Impurity
K4
K5
K6 1800 Hz
1100
800 Hz
900
KNH
SNH
1
1
9.0
1000
2
8.5
8.0
# of protons
7.5
7.0
6.5
6.0
5.5
1
5.0
2 3
4.5
4.0
11 2 2 3
2 3.5
3.0
2.5
2.0
TNH SNH
Threonine (Thr) (T) Serine (Ser) (S) Lysine (Lys) (K) 13 O O O 2 H 2 H 2
C/DEPT 600 MHz
H2N
CH C
3
HO CH
1
N
CH C
3 CH2
OH
4 CH3
1
N
CH C
3 CH2
1
ppm
OH
KNH
4 CH2 5
CH2
6 CH 2
K1
S1 NH2 T1
T3
T2 K2 S3
175
170
ppm
S2
K6
K3 K5
70 65 60 55 50 45 40 35 30 25
K4 T4
ppm
Answers for Student Exercises 5.11 ppm 9
F1
8
7
6
60 5
4
3
2
1
ppm
1
1
2
2
3
3
4
4
5
5
6
6
7
7
8
8
COSY 600 MHz K5 K4
T4
K3K3’ K6 S3 K2 T3T2 S2
TNH KNH SNH
COSY 600 MHz
ppm
F1
1.0
1.0
1.5
1.5
2.0
2.0
2.5
2.5
3.0
3.0
3.5
3.5
4.0
4.0
4.5
4.5 ppm
4.5
4.0
3.5
3.0
2.5
F2
2.0
1.5
1.0
T4 K4 K5 K3K3’
K6
S3 T2 T3K2 S2
Answers for Student Exercises 5.11 ppm 9
F1
8
7
6
61 5
4
3
2
1
ppm
1
1
2
2
3
3
4
4
5
5
6
TNH
TOCSY 600 MHz K5 K4
T4
K3K3’ K6 S3 K2 T3T2 S2
6
7
7
8
8
KNH2 KNH SNH
TOCSY 600 MHz
ppm
F1
1.0
1.0
1.5
1.5
2.0
2.0
2.5
2.5
3.0
3.0
3.5
3.5
4.0
4.0
K4 K5 K3K3’
K6
S3 T2 T3K2 S2
4.5 4.5
4.0
3.5
3.0
2.5
F2
2.0
1.5
1.0
4.5 ppm
T4
Answers for Student Exercises 5.11
62
COSY 600 MHz SNH
KNH
Threonine (Thr) (T) Serine (Ser) (S)
1.5
H2N
2
3
1
CH C 3 CH2
1
KNH
ROESY 600 MHz SNH
KNH2
KNH
KNH2 T4 K4 K5 K3
Lysine (Lys) (K)
O
2
H N
CH C
3 CH2
OH
4 CH3
2.0
O
2
H N
CH C
HO CH
F1
O
SNH
KNH2
ppm 1.0
TOCSY 600 MHz
1
OH
4 CH2 5
CH2
6 CH 2
2.5
K6
NH2
3.0 S3 T2 K2 T3
3.5 4.0
S2
4.5 9.0
8.5
8.0
ppm
7.5
8.5
F2
8.0
7.5
ppm
F2
8.5
8.0
7.5
7.0 ppm
F2 HMQC 600 MHz
T3 T2S3 K2
S2
ppm
Threonine (Thr) (T) Serine (Ser) (S)
20
H2N
30
2
O
CH C 3
HO CH 4 CH3
F1
K6
1
H N
2
O
CH C 3 CH2
OH
1
K5 K4 K3
T4
T4
Lysine (Lys) (K)
H N
O
2
CH C
3 CH2
1
K4 K5
OH
K3
4 CH2 5
K6
CH2
40
6 CH 2
NH2
50
K2 S2T2 S3
60
T3
4.5
4.0
3.5
3.0
F2
2.5
2.0
1.5
1.0
ppm
Answers for Student Exercises 5.11 ppm 9.0 8.5 8.0
ppm
63 4.0
3.5
3.0
2.5
2.0
1.5
1.0
HMBC 600 MHz ppm
T3 T2
20
K2
F1
K3 K5
K6
K3
T4 K4 K5
K4
K2
KNH-K3
30
K6
K5
K4
K3 K5
K4
K6
40
50 KNH-K2
K2 S2 T2 S3
K3 K3’ K4 S3 T3
60
T4
S2 T2
T4
T3
F2 SNH
KNH
KNH2 S2
ppm
168 170
S2-T1
SNH-T1
T2 K2 S3 T3
T3-T1
T4
K5 K4 K3
K6
T2-T1
T1 KNH-S1
S2-S1 K2-S1
T2,S3-S1 Threonine (Thr) (T) Serine (Ser) (S)
F1 172
H2N
O
2
CH C 3
HO CH
174
1
4 CH3
H N
2
O
CH C 3 CH2
OH
1
S1
Lysine (Lys) (K)
O
2
H N
CH C
3 CH2
1
OH
4 CH2 5
CH2
6 CH 2
176
NH2
178
KNH-K1
K2-K1
K3-K1
K1
180 9.0 8.5 8.0
ppm
4.0
3.5
F2
3.0
2.5
2.0
1.5
1.0
ppm
Answers for Student Exercise6.1 1
1 NOTE: The formula should be C5H10N2
H NMR 300 MHz
4
3
2
ppm
2.75 2.70 2.65 2.60 2.55 2.50 2.45 2.40 2.35 2.30 2.25 2.20 2.15 2.10 13
C/DEPT NMR 75.5 MHz
4
4 1
N
2
3
N
3
4
2
C5H10N2 Mol. Wt.: 98 3-(dimethylamino)propanenitrile
1
130 15
120
110
100
90
80
70
60
50
40
30
20
ppm
20
ppm
N NMR 30.4 MHz N
N
240
220
200
180
160
140
120
100
80
60
40
Answers for Student Exercise 6.2 1
2
H NMR 300 MHz 1 1
1
3
2 Si Cl 1 3 C6H15ClSi Mol. Wt.: 151
3
tert-butylchlorodimethylsilane
1.3 13
1.2
1.1
1.0
0.9
0.8
0.7
0.6
0.5
0.4
0.3
0.1 ppm
0.2
C/DEPT NMR 75.5 MHz
1 3
2
35 29
30
25
20
15
10
5
0
ppm
-5
Si NMR 59.6 MHz
55
50
45
40
35
30
25
20
15
10
5
ppm
Answers for Student Exercise 6.3 1
3 2
5
H NMR 300 MHz
3 4
H3C 1 P
2 34
5
Br C19H18BrP Mol. Wt.: 357
2340
8.5 13
8.0
7.5
7.0
6.5
2320
Hz
2300
6.0
5.5
5.0
4.5
4.0
3.0 ppm
3.5
C/DEPT NMR 75.5 MHz 4
3
a
b
10200
Hz
10000 Hz
1
5
2 3
2 c
d
4
9800
e
Hz 9000
8900 Hz
800
5
Hz
750
1 ab c 130 31
d 120
e 110
100
90
80
70
60
50
40
30
20
10 ppm
4
2 ppm
P NMR 121.5 MHz, 1H Decoupled
28
26
24
22
20
18
16
14
12
10
8
6
Answers for Student Exercise 6.4 % of Base Peak
MASS
4
105 175
100
244 77
50
127
50
205
100
m/z
IR
F3C
1
50
OH CF3
5'
2 3 4 5
6'
6 7
717
F NMR 282.4 MHz See Table 6.2
7
5,5’
972
1000 19
6,6’
1165 1219 1273
H NMR
1504
3070
4000 1
200
C9H6F6O Mol. Wt.: 244 1,1,1,3,3,3-hexafluoro2-phenylpropan-2-ol 3000 2000 Wavenumber (cm-1)
3548 3602
%Transmittance
100
150
OH 7.8
7.5 13
7.0
6.5
7.7
6.0
7.6
5.5
7.5 ppm
5.0
4.5
4.0
ppm
6,6’
5,5’
128
126
4
130
ppm
-74.7
Septet caused by 6 F two bond coupling (JCCF) to carbon 2
C/DEPT
7
-74.6
C1 and C3, with coupling to 3F, J value of 288 Hz
124
122
120
118 ppm
78
77
76
ppm
Answers for Student Exercise 7.7A
1
% of Base Peak
MASS
100
103
100
72
43
50
CI Reagent gas methane
x 30
57
50
85
40
50
60
70 m/z
IR
85
80
90
143
131
100
100
m/z
833
3000
H NMR 600 MHz
972 1049
2870 2954
4000 1
1149
1388 1458
50 3417
%Transmittance
100
2000 Wavenumber (cm-1)
1000
6 OH
2680 2660 2640 2620 2600 2580
2
4
4.5
5
4.0
2140 2120 2100 2080 2060 2040 Hz
Hz
2 is closer to CH2OH in space, therefore is more deshielded than 4. NOE experiments would confirm this.
OH
3.5
3.0
2.5
2.0
ppm
1.5
13 13
C/DEPT MHz C/DEPT NMR NMR 150.9 600 MHz 3-methyl-3-oxetanemethanol 5 CH2OH 2 1O
24
CH3
3 4
6
C5H10O2 Mol. Wt.: 102
5
6 3
80
75
70
65
60
55
50
45
40
35
30
25
20 ppm
Answers for Student Exercise 7.7B ppm
1.5
4.5
4.0
3.5
3.0
2 2.5
2.0
1.5
ppm
6
3-methyl-3-oxetanemethanol 5 CH2OH 2
2.0
1O
1.5
CH3
3 4
2.0
6
C5H10O2 Mol. Wt.: 102
2.5
COSY 600 MHz
2.5
F1 3.0
3.0
3.5
3.5
4.0
4.0
4.5
OH 5
2 4
4.5
2
4
5
ppm
OH
F2
HMQC 600 MHz
6
20
20
30
30
40
40
F1 50
50
60
60
70
70
80
80 4.5
4.0
3.5
3.0
F2
2.5
2.0
1.5
ppm
6
3
5
2 4
Answers for Student Exercise 7.8A
3
MASS % of Base Peak
221
100 50
97 55
203
177
50
IR
137
81
100
150
m/z
236
200
100 %Transmittance
1003
1
910
1381 1458
2924
4000
3000
H NMR 600 MHz
9
11’
11
2000 Wavenumber (cm-1)
12
2300
Hz
1200
8’
800
Hz
1150
750
1000
16
5’
Hz
1050
Hz
700
Hz
900
600
850
15
7
3’
31
5 9’ 4’
4
8 2350
1000
Hz
550
Hz
13 14
Hz
500
16
(-)-ambroxide 11 13
CH3 12
4 5
3 6
2
1 10 9
7
14
H3C 15CH3
O CH3
16
8
C16H28O Mol. Wt.: 236
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
Answers for Student Exercise 7.8B
4
13 13 C/DEPT
NMR 600 150.9 MHz C/DEPT NMR MHz
3 11
9
7 1
15
5
13
10
80
2
75
70
65
60
11’ 11
55
50
45
8
40
6
35
30
25
51 4’3
4
9’
ppm
8’
5’
20
15 ppm
HMQC 600 MHz
16
12 9
14,16 12 8 4
1513 14
3’
7
13 4 8 16 14 12
20
30
6 15 2
F1 40
39 5
(-)-ambroxide 11 13
CH3 12
50 4 5
60
3 6
2
14
ppm
1.9
1.8
O CH3
9
16
1.7
1.6
7
H3C 15CH3
4.0
1 10
7 1 11
8
F2
1.5
1.4
1.3
1.2
1.1
1.0
0.9
0.8
ppm
Answers for Student Exercise 7.8C 11
5
11’
12 9
ppm
4.0
3.9
ppm
2.0
8 1.8
51 4’ 3 8’ 9’
4 1.6
1.4
HMBC 600 MHZ HMQC 600 MHz 16 1513 14 5’ 3’ 7 1.2
1.0
0.8
ppm
13
15
4 20
8 14,16 12
ppm
6
34
15
(-)-ambroxide 11
F1
13
CH3 12
36 4 5
38
3 6
2
9
7
14
40
1 10
H3C 15CH3
2
O CH3
16
9 3
8
42
5 ppm
7
58 60
1
62 64
11
ppm
10
80 82 4.0
3.9
ppm
2.0
1.8
F2
1.6
1.4
1.2
1.0
0.8
ppm
Answers for Student Exercise 7.8D
6
INADEQUATE MHz INADEQUATE150.9 600 MHz
11 1
10
539
7
2
1416 12 8 4
15
6
13
Hz (-)-ambroxide 11 13
-7000
CH3 12
4 5
-6000 -5000
2-13 6-14 or 15
3 7
6
O 1 10 2 CH3 9
3-4 9-8
16
14
H3C 15CH3
-7000 -6000
5-4
8
-5000
6-15 or 14
-4000
-4000
5-6 7-8
-3000
3-2
-3000
1-12
-2000
-2000
11-12 7-6 7-2
-1000
-1000
1-2
F1
0
0
10-8
1000
1000
2000
2000 10-9
3000
3000
4000
4000
5000
5000 10-1
6000
6000
7000
7000
80
75
70
65
60
55
50
F2
45
40
35
30
25
20
15
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.1
% of Base Peak
MASS 68
55
100 41
112 84
50
97
40
50
60
70
IR
m/z O
90
100
110
1 2 3 4
50
Cycloheptanone C7H12O Mol. Wt.: 112
11
856 941
2000 Wavenumber (cm-1)
1161
3000
1342 1454
4000
1701
2858 2927
%Transmittance
100
80
1000
4
NMR 300 MHz HHNMR 2 3
2.7
2.6
2.5
2.4
2.3
2.2
2.1
2.0
1.9
1.8
1.7
1.5 ppm
1.6
1313
C/DEPT NMR 75.5 MHz C/DEPT
2
4
3
1
200
180
160
140
120
100
80
60
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.2
MASS % of Base Peak
124
100 94
50
53
50
60
95
81
66
70
80
m/z
IR
100
110
120
OH
100
3
50
4
2
5
1
687 768 837 945 1041 1149
11
1284
3000
m-Methoxyphenol C 7H 8 O 2 Mol. Wt.: 124
1493 1601
2839 2947 3005
4000
7
OCH3
6
3398
%Transmittance
90
2000 Wavenumber (cm-1)
1000
H NMR NMR 300 MHz H 6
5
7
2 4
2150
2140
Hz
1960
1950
Hz
1920 Hz
1930
OH
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
ppm
13 13
C/DEPT NMR 75.5 MHz C/DEPT
4 1
5
3 2
7
3 1 190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.3
MASS % of Base Peak
55 M-1 83
100 39 41
M
50
53
40
45
65
50
55
IR
m/z
60
84
66
65
70
75
80
85
50 741
2000 Wavenumber (cm-1)
1014
11
1138 1227 1319
3000
1454
4000
2229 2291
2877 2939 2978
3332
%Transmittance
100
1000
H H NMR NMR 300 MHz
5 1
4 1280
4.0
1260 Hz
3.5
OH
660 Hz
680
3.0
2.5
2.0
ppm
1.5
13 13C/DEPT
C/DEPT NMR 75.5 MHz
3
HO
4
H 2C
C
C
1
2
3
CH2 5 CH3
2-Pentyn-ol C5 H 8 O Mol. Wt.: 84
CDCl3
5 4
1 78.0 77.5 77.0 76.5
2
95
90
85
80
75
70
65
ppm
60
55
50
45
40
35
30
25
20
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.4
MASS % of Base Peak
75
CI Reagent gas methane
100 49 61
50
77 99 97
m/z
IR
146 148 146
100
113
100
112 M 114
50
x 30
111
110 75 77
50
150
148 150 152
115
100
150
m/z
Cl Cl 1 CH 3 Cl CH2 2 CH2
90 80
1,2,3-Trichloropropane C3H5Cl3 Mol. Wt.: 146
70
H NMR NMR 300 MHz
663 717
1 1H
2000 Wavenumber (cm-1)
910
3000
1219 1288
4000
1435
2962 3016
%Transmittance
100
1000
1+3
2
4.35
4.30
4.25
4.20
4.15
4.10
4.05
4.00
3.95
3.90
3.85
ppm
3.80
13 13C/DEPT
C/DEPT NMR 75.5 MHz
1+3 2
75
70
65
60
55
50
45
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.5
% of Base Peak
MASS
m/z 126 (M) 127 (M+1) 128 (M+2)
100 50
%M 100.0 8.2 4.9
111
126
39 43
40
83
57
49
50
60
70
80 m/z
IR
90
100
110
120
130
50
11
590
2000 Wavenumber (cm-1)
725
856 933 1061
1273
3000
1415
4000
1662
3089
%Transmittance
100
1000
H H NMR NMR 300 MHz 3
1
2300
2280 Hz
4
7.5
7.0
6.5
6.0
5.5
6
2
5.0
2120 Hz
2140
5
4.5
13 13 C/DEPT
C/DEPT NMR 75.5 MHz
4.0 2
3.5
3.0
2.5
ppm
3
1
S
4
O 5 6 CH3
1
5
3
2
Ethanone, 1-(2-thienyl)2-Acetylthiophene C6H6OS Mol. Wt.: 126
6
4
190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.6
% of Base Peak
MASS
x 10
105
100
186 184
50
77
51
50
IR
100
150
m/z
100
80 70
2
3
2260
2250
2240
2230
2220
13
7.0
6.5
6.0
1000
6
4
2210
5.5
5.0
C/DEPT NMR 75.5 MHz
1590
1580
1570
Hz
640
630
620
Hz
Hz
2200
5
7.5
594 694 764
H NMR 300 MHz
2000 Wavenumber (cm-1)
964
1
3000
1211
4000
1450 1496
2985 3032
%Transmittance
90
4.5
H3C 6
5
4.0
3.5
3.0
2.5
ppm
Br
1 2 3 4
(1-Bromoethyl)benzene C8H9Br Mol. Wt.: 184
4 3
2
6
5
1 140
130
120
110
100
90
80
70
60
50
40
30 ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.7
MASS % of Base Peak
109 124
100
81 53
50
63
50
75
60
70
80
IR
90
m/z
100
110
120
50
513
733 825
2000 Wavenumber (cm-1)
1034
11
1234
3000
1512 1612 1701
4000
1859
2835 2951
3348
%Transmittance
100
1000
H H NMR NMR 300 MHz 2
5
3
OH
7.0
6.5
6.0
5.5
5.0
4.5
4.0
ppm
3.5
OH
13 13
C/DEPT C/DEPT NMR 75.5 MHz
4 3 2 1
OCH3 5
3 1
p-Methoxyphenol C 7H 8 O 2 Mol. Wt.: 124
2
5
4
150
140
130
120
110
100
90
80
70
60
50
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.8
MASS % of Base Peak
128
100 64
130
50
92 73
50
60
70
80
IR
90
m/z
100
110
120
130
50
2000 Wavenumber (cm-1) OH
1 1H
H NMR NMR 300 MHz 6
3
1
4 6
5
1000
Cl
2 3
5
679 748
3000
1030
4000
1200 1338 1454 1481 1585
3039 3074
3464 3521
%Transmittance
100
OH
4
o-Chlorophenol C6H5ClO Mol. Wt.: 128
7.4
7.2
7.0
6.8
6.6
6.4
6.2
6.0
5.8
5.6
5.4
ppm
13 13
C/DEPT C/DEPT NMR 75.5 MHz
5
4
3
1
155
6
2
150
145
140
135
130
125
120
115
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.9 x 20
55 87
100
115 196 194
73 135
0
50
100
137
165
150
m/z
IR
163
1203
50
1365 1435
% of Base Peak
MASS
50
3000
2000 Wavenumber (cm-1)
1 1H
H NMR NMR 300 MHz
748
4000
1736
2954
%Transmittance
100
1000
O 6
6 Br
5
4
3
1
2
O
Methyl 5-bromo valerate C6H11BrO2 Mol. Wt.: 194
5
2 4
3.6
3.4
3.2
3.0
2.8
2.6
2.4
2.2
2.0
3
1.8
1.6
ppm
13 13
C/DEPT C/DEPT NMR 75.5 MHz
5 2
4
3
6 1
33.0
32.5
170 160 150 140 130 120 110 100
32.0
90
ppm
80
70
60
50
40
30
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.10
MASS % of Base Peak
54
100
67
84 93
50
111
50
60
70
80
IR
m/z
90
100
126
110
120
7
1 1H
H NMR NMR 300 MHz
6
2000 4 OH 5 1 Wavenumber (cm-1) 2
849
3000
1045
8
1331
4000
1466
2873 2931 2958
3344
%Transmittance
100
1000
3
8
3-Octyn-1-ol C8H14O Mol. Wt.: 126
1
2
6 7
5
OH
3.5
3.0
2.5
2.0
1.5
ppm
1.0
13 13C/DEPT
C/DEPT NMR 75.5 MHz
6
1
2 84
82
80
85
5
8
ppm
78
4
7
3 80
75
70
65
60
55
50
45
40
35
30
25
20
ppm
CHAPTER 8 ASSIGNED PROBLEMS
% of Base Peak
MASS
Problem 8.11 162
100
164
63 98
50
126
73
50
60
70
80
90
100 110 m/z
IR
120
128
130
140
150
160
50
1 1H
H NMR NMR 300 MHz
2000 Wavenumber (cm-1)
3
1000
OH
6
1
2
6
5
Cl
3
5
OH
4
7.4
7.2
7.0
555
3000
725 814
4000
1188 1277 1404 1477 1585
3097
3521
%Transmittance
100
6.8
6.6
Cl 2,4-Dichlorophenol C6H4Cl2O Mol. Wt.: 162 6.4 6.2 6.0
5.8
5.6
5.2 ppm
5.4
13 13C/DEPT
C/DEPT NMR 75.5 MHz
3
5
6
1
155
150
145
140
135
130
4
2
125
120
115
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.12 % of Base Peak
MASS
123
100
95 75
50
50
63
70
80
90 m/z
100
110
120
1157 1265 1358
60
1597 1685
50
IR
138
130
140
50
1
3000
2000 Wavenumber (cm-1)
H NMR 300 MHz 2
3
567
4000
841 960
3005 3074
3356
%Transmittance
100
1000 19
F NMR 282.4 MHz
1
H Coupled
1
H Decoupled
6 2400
2390
2380
Hz
2140
Hz
2130
ppm
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 13
-104.5 ppm
-104.4 5
C/DEPT NMR 75.5 MHz
6
COCH3
1 2 3 4
2
5
4
F 4-Fluoroacetophenone C8H7FO Mol. Wt.: 138
3
130 128 126 124 122 120 118
6 ppm
1 190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.13
MASS % of Base Peak
96
100 50
70
50
50
55
60
65
75 77
70 m/z
IR
75
80
85
90
95
F
100
2 3 4
95
2000 Wavenumber (cm-1)
756
3000
1234
4000
1504 1604 1697
Fluorobenzene C 6H 5 F Mol. Wt.: 96
3062
3749
%Transmittance
1
1000
11H
19
NMR 300 MHz H NMR
F NMR 282.4 MHz 1
H Coupled
2
3
4
7.4
7.3
7.2
7.1
ppm
-80.1
-80.3 ppm
-80.2
13 13
C/DEPT C/DEPT NMR 75.5 MHz
3
2 4
130
128
126
124
122
120
118
116 ppm
1 165
160
155
150
145
140
135
130
125
120
115 ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.14
MASS % of Base Peak
82
100 50
138
54
95
67
50
60
70
80
90 m/z
IR
123
100
110
120
130
140
50
6
1750
1740 Hz
Hz
640
570
1000
89
7
4
525
H NMR NMR 300 MHz
2000 Wavenumber (cm-1)
903
1 1H
1246
3000
1381
4000
1670
2870 2958
%Transmittance
100
560 Hz
300
3.5
3.0
Hz
290
2
6.0
5.5
5.0
4.5
4.0
2.5
13 13
C/DEPT C/DEPT NMR 75.5 MHz
2.0
ppm
1.5
7
CH3 3 4 9
2 5
H 3C H3 C
1 6
O
89
8
Isophorone C9H14O Mol. Wt.: 138
2 1 200
6 4
7
3 180
160
5 140
120
100
80
60
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.15
MASS % of Base Peak
54
68
50
81 79
50
60
70
93
80
90
IR
95
m/z
107
100
109
149 147 119
110
121
120
130
140
150
100 %Transmittance
90 80
H H NMR NMR 300 MHz Br
4
756
2000 Wavenumber (cm-1) 2
11
4
1250
3000
1435
4000
2245
2970
70
3
1000
1
2
3
N 4-Bromobutanoyl nitrile C4H6BrN Mol. Wt.: 147
3.6
3.5
3.4
3.3
3.2
3.1
3.0
2.9
2.8
2.7
2.6
2.5
2.4
2.3
ppm
2.2
13 13
C/DEPT C/DEPT NMR 75.5 MHz
3
2
4 1 120
110
100
90
80
70
60
50
40
30
20
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.16
MASS % of Base Peak
106
100 137
50 77
50
60
70
80
IR
m/z
90
100
110
120
130
140
90 80
1 1H
H NMR NMR 300 MHz
2000 Wavenumber (cm-1)
1000
6
3 2
OH 5
7.5
825
3000
1049
1442 1512 1620
4000
2931
3194
3348
%Transmittance
100
7.0
6.5
4
3
6.0
5.5
5.0
5
ppm
2
4.5
4.0
3.5
3.0
2.5
2.0
1.5 ppm
OH
13 13
C/DEPT C/DEPT NMR 75.5 MHz
6
5 1
OH
2 3
2
3
4
NH2
4
1 140
130
6
5
p-Aminophenylethanol C8H11NO Mol. Wt.: 137
120
110
100
90
80
70
60
50
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.17
MASS % of Base Peak
119
100 50
91
64 76
50
60
70
80 m/z
IR
90
100
110
120
90 80 70
H NMR NMR 300 MHz 2
671 787
1 1H
1342
3000
1481 1589
4000
2245
3309
%Transmittance
100
2000 Wavenumber (cm-1)
1000
3
OH
7.6
7.5
7.4
7.3
7.2
7.1
7.0
6.9
6.8
6.7
6.6
6.5
6.4
6.3
ppm
6.2
13 13
C/DEPT C/DEPT NMR 75.5 MHz 2 5
N
C
1
3 4
OH
p-Cyanophenol C7H5NO Mol. Wt.: 119
2
3
4
165
160
5
155
150
145
140
135
130
125
120
1 115
110
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.18
MASS % of Base Peak
163
100 178
50 91
77
50
135
100
IR
150
m/z
%Transmittance
100
50
2000 Wavenumber (cm-1)
748
11
1149 1203
3000
1458
2870 2962
3572
4000
1000
H H NMR NMR 300 MHz
3
6
2100 Hz
2150
950 Hz
1000
4
450
OH
7.0
6.5
6.0
5.5
5.0
Hz
400
5
4.5
4.0
3.5
13 13C/DEPT
C/DEPT NMR 75.5 MHz
2.5
1.5 ppm
2.0
6
OH 1
3.0
2
5 6
3 4
2,6-Diisopropyl phenol C12H18O Mol. Wt.: 178
3
6 5
4 1 150
2 140
130
120
110
100
90
80
70
60
50
40
30
20 ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.19
MASS % of Base Peak
106 78
100
121
51
50
50
60
70
80 m/z
IR
90
100
110
120
50
2
1000
4 7
5
2720
9.0
702
H NMR NMR 300 MHz
957
1 1H
2000 Wavenumber (cm-1) 3
1273
3000
1419
1689
4000
3047
3363
%Transmittance
100
2700 Hz
8.5
2580 Hz
2600
8.0
7.5
7.0
2440
6.5
6.0
2420 Hz
5.5
13 13C/DEPT
2180 Hz
2200
5.0
4.5
4.0
3.5
ppm
3.0
3
C/DEPT NMR 75.5 MHz
4
2
5
1
N
7 6
C
CH3
O
5 6
4
2
3
2-Acetylpyridine C7H7NO Mol. Wt.: 121
7
1
190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.20
MASS % of Base Peak
108
123
100 53
50
40
80
50
60
70
80
IR
90
m/z
100
110
120
50
2000 Wavenumber (cm-1)
1000
7
5
4
7.0
2060 3
6.5
Hz
Hz 1820
2020
633 741
H NMR NMR 300 MHz
1095
1 1H
1404
3000
1651
4000
2947
3109
%Transmittance
100
Hz
2
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
ppm
13 13
C/DEPT C/DEPT NMR 75.5 MHz 3 4
1
N
4
2
H3C5
3
2 7 6
CH3
O
1-Methyl-2-acetylpyrrole C7H9NO Mol. Wt.: 123
1
5
7
6 180
160
140
120
100
80
60
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.21
% of Base Peak
MASS
100
159
100
85
57
50
CI Reagent gas methane
x 20
43
103
158
50 50
100
m/z
IR
187
150
150
m/z
50
2000 Wavenumber (cm-1)
11
1034 1149
3000
1319
4000
1651 1720
2962
%Transmittance
100
1000
H H NMR NMR 300 MHz 7 1 3 5 6
3.5
3.0
2.5
2.0
1.5
ppm
1.0
13 13C/DEPT
C/DEPT NMR 75.5 MHz 7 1 2
3
4
O
6
5
7
O O Isobutylacetoacetate C8H14O3 Mol. Wt.: 158
2
200
5
3
6
7
1
4
180
160
140
120
100
80
60
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.22
MASS % of Base Peak
119
100 50
91
64 76
50
60
70
80
IR
90
m/z
100
110
120
100
80 70
11
H NMR 600 300 MHz 42 5
671 787
3000
1342
4000
1481 1589
2245
3309
%Transmittance
90
2000 Wavenumber (cm-1) OH
1000
3 4
6
2 1
5
7
C
6
OH
N
m-Cyanophenol C7H5NO Mol. Wt.: 119
7.4
7.3
7.2
7.1
7.0
6.9
6.8
6.7
6.6
6.5
6.4
6.3
ppm
6.2
13 13 C/DEPT
NMR 600 75.5MHz MHz C/DEPT NMR
5
6
4
2
3
1
7 155
150
145
140
135
130
125
120
115
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.23
MASS % of Base Peak
x 20 183
185
100 155
75
50
100
157
150 m/z
IR
224
200 198
264 262 260
226
200
250
50
H NMR NMR 300 MHz
6
3
2
617
1 1H
810
2000 Wavenumber (cm-1)
995 1068
3000
1223
1396 1485 1585 1685
4000
2962 3059 3089
3356
%Transmittance
100
1000
8
5
7
7.9
7.8
7.7
7.6
ppm
3.6
3.4
13 13C/DEPT
C/DEPT NMR 75.5 MHz
3.2
3.0 6
5
7
2.8
2.6
ppm
2.4
8
COCH2CH2CH2Cl 1 2 3 4
3
2
5 1
Br 4’Bromo-4-chlorobutyrophenone C10H10BrClO Mol. Wt.: 260
6
7
8
4
190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.24 % of Base Peak
MASS
100
100
CI Reagent gas methane
55
50
147 69
74 83
50
128
175
50
100
150
150
m/z
187
200
m/z
IR
50
H NMR NMR 300 MHz
930
1 1H
1238 1277 1419 1466
3000
1709
4000
2669
2978 3039
%Transmittance
100
2000 Wavenumber (cm-1)
1000
4
2x OH
6
x64
3 2
12
11
ppm
2.6
2.4
2.2
2.0
1.8
1.6
1.2 ppm
1.4
13 13C/DEPT
C/DEPT NMR 75.5 MHz O HO 1
O
3
CH2 C 5 CH CH2 OH 2
CH3
4
6
15
2-Methyl glutaric Acid C6H10O4 Mol. Wt.: 146
180 170 160 150 140 130 120 110 100
90
80
70
60
50
2
4 3
40
30
6
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.25 91 66
100
93
92
CI Reagent gas methane
50
100
51
% of Base Peak
MASS
50
50
60
m/z
IR
70
80
80
90
90
m/z
90 80
2000 Wavenumber (cm-1)
H NMR 300 MHz
725 802
1065
1
3000
1342
4000
1720
2962 3055
%Transmittance
100
1000
3
2 1
2050
7.0 13
6.5
Hz
2040
6.0
5.5
1080 Hz
1090
5.0
4.5
Hz
615 610 605
4.0
3.5
3.0
2.5
2.0
ppm
C/DEPT NMR 75.5 MHz
3
2
1
1
Bicyclo[2,2,1] hepta-2-5-diene C7 H 8 Mol. Wt.: 92
140
130
120
110
100
3
2
90
80
70
60
50
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.26
% of Base Peak
MASS
M 156
100 M+2
63
158
50 98
50
60
70
80
121
90
100 110 m/z
IR
120
130
140
150
160
6
1041
H NMR 600 MHz
1234
1473
3000
802
933
50
4000 1
586
2900
%Transmittance
100
2000 Wavenumber (cm-1)
1000
3
7
4
6.85
6.80
6.75
6.70
6.65
ppm
6.00 5.95
ppm
1313
C/DEPT MHz C/DEPTNMR NMR600 150.9 MHz 3 4
2
O 7
5 1
Cl
6
O
5-chloro-1,3-benzodioxole C7H5ClO2 Mol. Wt.: 156
1 155
150
4
7
5
2 145
36
140
135
130
125
120
115
110
105 ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.27A
% of Base Peak
MASS 55
42
100 84
50
114
70
40
50
60
70
IR
m/z
80
90
100
110
50
O 2
1000
1 O
1
6
2 6
3 4
571
H H NMR NMR 300 MHz
2000 Wavenumber (cm-1)
856
11
1057 1165
3000
1442
4000
1728
2931
%Transmittance
100
4
3 5
5
ε-Caprolactone C6H10O2 Mol. Wt.: 114
4.0
3.5
3.0
2.5
2.0
ppm
1.5
13 13 C/DEPT
C/DEPT NMR 75.5 MHz
43
6
2
5
1
170
160
150
140
130
120
110
100
90
80
70
60
50
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.27B
ppm 4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.5
ppm
1.5
COSY 300 MHz
4 1
O
2.0 2
2.5
2.0 O
1
F1
2.5
6
3 4
3
4
5
6
2
5
ε-Caprolactone C6H10O2 Mol. Wt.: 114
3.0
2
5 3
3.0
3.5
3.5
4.0
4.0 6
F2 ppm
6
2
5
HETCOR 75.5MHz MHz HETCO 300
4 3
1.5
1.5
2.0
2.0
2.5
2.5
3.0
3.0
3.5
3.5
4.0
4.0
4.5
4.5 ppm
F1
65
60
55
50
45
F2
40
35
30
25
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.28A
MASS % of Base Peak
CI Reagent gas methane 55
x 10
69
100
82
137
120 118
90
50
5
139
92
50
100
m/z
IR
130
140
m/z
150
50
H NMR 600 MHz 1
2000 Wavenumber (cm-1)
648 725
1
3000
1057
4000
1458
2862 2939
3332
%Transmittance
100
1000
6 HO 1
3
2
4
5 6
Cl
2
5
1-Hexanol-6-chloro C6H13ClO Mol. Wt.: 136
4 3
OH
3.6
3.4
3.2
3.0
2.8
2.6
2.4
2.2
2.0
1.8
1.4 ppm
1.6
1313 C/DEPT
MHz C/DEPTNMR NMR600 150.9 MHz
1
5
6
60
55
50
45
40
35
2
4
30
3
25
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.28B
3.5
ppm
3.0
2.5
1.5
ppm
1.5
1.5
2.0
2.0 HO 1
F1
2.0
2
3
4
5 6
Cl
1-Hexanol-6-chloro C6H13ClO Mol. Wt.: 136
2.5
2.5
3.0
3.0
3.5
3.5
1
6
OH
ppm
F2
5
HMQC 600 MHz
2 4 3
25 30
COSY 600 MHz
3
25 4
OH
30
35
35
40
5
F1
40
2
45
ppm
45
50
32
50
55
6
55 33
60
2.0 3.5
3.0
1.8 2.5
F2
1.6
1.4 2.0
ppm 1.5
60 1
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.29A
MASS % of Base Peak
95
100 67
45
50
69
55
110
81
50
60
70
80
IR
128 113
90
m/z
100
110
120
130
%Transmittance
100
50
2000 Wavenumber (cm-1)
11
825
1041 1126
3000
1377 1450
2924 2966
3344
4000
1000
HNMR NMR 300 MHz H
1 7
Hz
1540
Hz
1140
5
480 Hz
500
4.5
3
Hz
440
2
5.0
4
4.0
3.5
3.0
8
2.5
OH
2.0
ppm
1.5
13 13 C/DEPT
C/DEPT NMR 75.5 MHz
7
OH 5
8
5
4
3
2
1
120
110
100
90
80
3
2
6-Methyl-5-hepten-2-ol C8H16O Mol. Wt.: 128
6
130
6
4
1
8 7
70
60
50
40
30
20 ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.29B
ppm 5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0 ppm
1.0
COSY 300 MHz
1.0 1
1.5
3
2.0
2.0
OH 4
2.5
2.5
F1 3.0
3.0
3.5
3.5
4.0
4.0
4.5
4.5
5.0
5.0
1.5
7 8
2
F2 2
5
3
ppm
84 1
HETCOR300 75.5 MHz HETCO MHz
7
1.0 7
OH
1.5 5
F1
6
4
3
2
2.0
8
2.5
6-Methyl-5-hepten-2-ol C8H16O Mol. Wt.: 128
1
3.0 3.5
OH
4.0 4.5 5.0 5.5 120
100
80
60
F2
40
20
5
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.30A
MASS
CI Reagent gas methane 223 225
100 69
100
0
143
50
100
177
159
179 50 194
150
m/z
230
240 250 m/z
IR
263 265
50
251 253
% of Base Peak
88
260
%Transmittance
100
50
6
1000
8
2
5
3.5
1034
H NMR NMR 300 600 MHz MHz
4.0
1188
2000 Wavenumber (cm-1)
11 H
7
1458
3000
1736
2870 2939
4000
3.0
2.5
3
2.0
4
ppm
1.5
13 13 C/DEPT
NMR 75.5 600 MHz C/DEPT NMR MHz
Br
6
5
4
3
2
1
O
7
8
2,6,5 7
O
1
4 3 8
Ethyl 6-Bromohexanoate C8H15BrO2 Mol. Wt.: 222
170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.30B
ppm
4.0
3.5
3.0
2.5
2.0
1.5
1.0
1.0
F1
ppm
COSY 300 MHz
1.0
1.5
1.5
2.0
2.0
2.5
8 4 3 5 2
2.5 1 1
3.0
3.0 6
3.5
3.5
4.0
4.0
F2 2 6 5 4 3
7
8
7
HETCOR HETCO75.5 300MHz MHz
ppm 1.0 Br
6
5
4
3
2
1
O
7
1.0
8
8
O 1.5 Ethyl 6-Bromohexanoate C8H15BrO2 Mol. Wt.: 222 2.0
1.5
2.0
F1 2.5
2.5
3.0
3.0
4 3 5 2
6
3.5
3.5
4.0
4.0 60
55
50
45
40
35
F2
30
25
20
15
ppm
7
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.31A
MASS % of Base Peak
134
100 41 94
50
65
40
50
77
60
119
91 105
70
80
IR
m/z
90
100
110
120
130
50
2000 Wavenumber (cm-1)
690 752
1
3000
1242
4000
1496 1601
2866 2916 3032 3066
%Transmittance
100
1000
H NMR 600 MHz 5
2
3 4
3680
Hz 3300
3660
Hz 3220
3280
Hz
3200
6
7.4
7.2
7.0
6.8
6.6
6.4
6.2
2760
2740
Hz
7
6.0
5.8
5.6
5.4
5.2
5.0
ppm
4.8
13 13
C/DEPT NMR NMR 150.9 600 MHz C/DEPT MHz 5
6
7
OCH2CH=CH2 1 2
3 4 6
1
160
150
140
130
3
2 4
7
120
5
Allylphenyl ether C9H10O Mol. Wt.: 134
110
100
90
80
70
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.31B
ppm 7.5
7.0
6.5
6.0
5.5
5.0
4.5
ppm
4.5
4.5
5.0
5.0
5.5
5.5
6.0
6.0
6.5
6.5
7.0
7.0
COSY 600 MHz
F1
3
4
2
F2
6
ppm 5
6
7
OCH2CH=CH2
70
HMQC 600 MHz
5
7
5
70
1 2
80
80
3
90
90
4
Allylphenyl ether C9H10O Mol. Wt.: 134
100
100
F1 110
110
diastereotopic
2
120
120
130
130
7
3 6
140
140
150
150 1
7.5
7.0
6.5
6.0
F2
5.5
5.0
4.5
ppm
4
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.32A
% of Base Peak
MASS x 20
95
100 50
110 109
67
55
70
80
90
IR
100 m/z
110
120
130
1365
60
1712
50
139 136
121
154
140
150
50
H NMR 600 MHz
2000 Wavenumber (cm-1) 3
829
1
3000
1057
4000
1227
2877 2951
3317
%Transmittance
100
1000
8 9 10
OH
2400
2
Hz
1350 Hz 1150
Hz 1050
Hz
950 Hz
4.0
3.5
3.0
Hz
750
In the above insets each tick mark is 10 Hz 3
6
2.5
550 Hz
5 4
2.0
500 Hz
5 6
3
ppm
1.5
13 13
C/DEPT NMR NMR 150.9 600 MHz C/DEPT MHz 10
9
H 3C
CH3 7
6
2
1 4
5
8
CH3
3 OH
4
Borneol C10H18O Mol. Wt.: 154
2
3
5
6
9 10
25
20
8
1 7
75
70
65
60
55
50
45
40
35
30
15 ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.32B
ppm
4.0
3.5
3.0
2.5
7 2.0
1.5
1.0
ppm
COSY 600 MHz 9.10,8
1.0
3
1.0
5
1.5
1.5
2.0
2.0
F1
10
2.5
6
3.0 5
3.5
8
CH3
3.0
2
1 4
4
2.5
CH3 7
5 6 3
9
H 3C
OH
6
3 OH
3.5
Borneol C10H18O Mol. Wt.: 154
4.0
4.0
F2
2
HMQC 600 MHz
ppm 8
ppm 20
10 9
20
6 5
15 30
30 20
40
F1
diastereotopic
25 0.90
0.85
3
40
ppm
50
50
60
60
70
70
4
7 1
2
4.0
3.5
3.0
2.5
F2
2.0
1.5
1.0
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.33A
MASS % of Base Peak
85
100 50
57
70
50
60
70
IR
114
m/z
80
90
100
110
656
1180
1774
4000 1
972
50
1358 1466
2885 2970
%Transmittance
100
3000
H NMR 600 MHz
1000
6 2
3
6
4
1
2
O
O
5
4
2000 Wavenumber (cm-1)
3
3 5
5
γ-Caprolactone C6H10O2 Mol. Wt.: 114
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
13 13
C/DEPT NMR NMR 150.9 600 MHz C/DEPT MHz
2
5
3
4
1
180
6
29
160
140
120
100
80
28
60
ppm
40
20
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.33B
ppm 4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
COSY 600 MHz
ppm
1.0
1.0
1.5
1.5
6
5 3
2.0
2.0 3
F1 2.5
2
2.5 2
3
6
4
3.0
1
3.0
O
O
5
γ-Caprolactone C6H10O2 Mol. Wt.: 114
3.5
3.5
4.0
4.0 4
F2
HMQC 600 MHz
ppm 10
10
20
20
30
30
6
diastereotopic
40
40
ppm
F1 50
3 5 2
28
60
50 60
30 2.5
2.0
1.5 ppm
70
70
80
80
4.5
4.0
3.5
3.0
2.5
F2
2.0
1.5
1.0
ppm
4
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.34A
MASS % of Base Peak
41 69
100
81
55
95
50
123
109
60
70
80
90
IR
m/z
100
110
120
130
140
1057
50
156
1381 1450
40
138
150
160
50
4000 1
3000 HO
H NMR 600 MHz
2000 9 10 Wavenumber (cm-1) CH3 CH3
1
6
2
3 4
5
833
2924
3332
%Transmittance
100
1000
9
7
8 10
CH3 8
Citronellol C10H20O Mol. Wt.: 156
6
1
5.0
4.5
3
5 OH
4.0
3.5
3.0
2.5
2.0
2
4
1.5
ppm
1.0
13 13
C/DEPT NMR NMR 150.9 600 MHz C/DEPT MHz
9
6
24
1
3
8
10
7
130
5
26
120
110
25
100
ppm
90
80
70
60
50
40
30
20 ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.34B
ppm 5.5
F1
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
1.0
1.0
1.5
1.5
2.0
2.0
2.5
2.5
3.0
3.0
3.5
3.5
4.0
4.0
4.5
4.5
5.0
5.0
F2
COSY 600 MHz 10 4 2
3 8 9
OH 5
1
6
HMQC 600 MHz
ppm HO
20 CH3 2
10
9
10
1
6
3
8
20
CH3
40
95 3 4 2
60
1
7
CH3
40 4 5 Citronellol C10H20O Mol. 60 Wt.: 156
8
ppm
F1 80
80 20
100
100
30 40
120
120
5.5
5.0
4.5
4.0
3.5
3.0
F2
2.5
2.0
7
ppm
2.0 1.5 1.0 1.5
1.0
6
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.35A
MASS % of Base Peak
95 81
100
41 108
69
55
50
152 137
50
60
70
80
90 100 m/z
IR
9
130
140
10CH3
2954
O
Camphor C10H16O Mol. Wt.: 152
1743
3000
1041
1
748
3
1450
6
50
1273
4 2
4000
2000 Wavenumber (cm-1)
1000
H NMR 600 MHz
2.3
8 9
4
3
2.4
150
8
5
%Transmittance
120
H3C 7 CH3
100
1
110
3 5
2.2
2.1
2.0
1.9
6 1.8
1.7
5
6 1.6
1.5
1.4
10
1.3
1.2
1.1
6
5
9
30
25
1.0
ppm
0.9
13 13
C/DEPT NMR NMR 150.9 600 MHz C/DEPT MHz
4 3 2
220
1
ppm
10
8
7
55
50
45
40
35
20
15
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.35B
ppm
F1
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
0.8
0.6
ppm
0.6
0.6
0.8
0.8
1.0
1.0
1.2
1.2
1.4
1.4
1.6
1.6
COSY 600 MHz
10 9 8 5 6 6
1.8
1.8
2.0
2.0
2.2
2.2
2.4
2.4
5
3
4
F2
3
HMQC 600 MHz
ppm 10
10
10
20
20
8 9
9
30
8
30
H3C 7 CH3
F1
4
5
3 2
40
6
40
1 10CH3
4
O
Camphor C10H16O Mol. Wt.: 152
50
5 6
3 7
50 1
2.4
2.2
2.0
1.8
1.6
F2
1.4
1.2
1.0
0.8
0.6
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.35C
INADEQUATE INADAQUATE150.9 150.9MHz MHz 2
1
3
Hz 9
-20000
8
-20000
H3C 7 CH3
-15000
4
5
-15000
3 2
6
-10000
1
-10000
10CH3
-5000
O
-5000
Camphor C10H16O Mol. Wt.: 152
F1 0
0
5000
5000
10000 220
200
180
160
140
120
100
F2
80
60
5
9 8
40
10000 ppm
20
Hz
1
7 43
6
10
-25000
-25000
-24000
-24000
-23000
-23000
-22000
-22000
F1 -21000
-21000
-20000
-20000
-19000
-19000
-18000
-18000
-17000
-17000 ppm
65
60
55
50
45
40
35
F2
30
25
20
15
10
5
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.36A
% of Base Peak
MASS
x 30
43 70
100 55
50 40
50
130
115
60
70
80
IR
m/z
90
100
110
120
130
1041
2962 1242
1743
50 4000
1
1373 1466
2877
%Transmittance
100
3000
2000 Wavenumber (cm-1) 1
H NMR 600 MHz
2350 Hz
2300 Hz
1000 Hz
850
Hz
1000 7 is doublet
6 is triplet
Hz
700
Hz
550
In the above insets each tick mark is 10 Hz
3
4
3.5
3.0
2.5
2.0
5
5 ppm
1.5
13 13
C/DEPT NMR NMR 150.9 600 MHz C/DEPT MHz
O 3
H3C 2 O
4
5
1
6
CH3
3
7 CH3
2
5 4
2-Methylbuty acetate C7H14O2 Mol. Wt.: 130
170 160 150 140 130 120 110 100
90
80
70
60
50
40
7 6 1
30
20
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.36B
ppm 4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
COSY 600 MHz 6
1.0
1.0
1.5
1.5
5 5
7
4
2.0
2.0
2.5
2.5
3.0
3.0
3.5
3.5
4.0
4.0
1
F1
3
F2
HMQC 600 MHz
ppm 10
10 ppm 10
6
20
20
6 7 1 5
15
30
30
7 0.95
40
0.90
4
ppm
0.85
40
F1 O
50
50
3 4
H3C 2 O
5
1
60
6
CH3
60
7 CH3
2-Methylbuty acetate C7H14O2 Mol. Wt.: 130
70
4.5
4.0
3.5
3.0
2.5
F2
2.0
1.5
70
1.0
ppm
3
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.37A
MASS
m/z 151 (M-1) 152 (M) 153 (M+1) 154 (M+2)
% of Base Peak
111
100
%M 37.5 100.0 12.7 5.2
152
50 83
69
50
60
70
80
90
IR
m/z
100
110
120
130
140
150
1234
1419
1651
3000
2000 Wavenumber (cm-1)
H NMR 600 MHz
725
957
50
4000 1
1057
3008 3093
%Transmittance
100
1000
7 and 8 are diastereotopic 78
Hz
4680
3
1
2
7.5
7.0
4260 Hz 1520
Hz
4560
Hz 740
720 Hz
Hz
600
6
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
ppm
1.5
13 13
C/DEPT NMR NMR 150.9 600 MHz C/DEPT MHz O S
4
1 2
1 5
3
3
C 5
6
7 8
cyclopropyl(thiophen-2-yl)methanone C8H8OS Mol. Wt.: 152
2
7 8 6
4 180
160
140
120
100
80
60
40
20
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.37B
ppm
8
7
6
5
4
3
2
1
ppm
1
1
2
2
COSY 600 MHz 87
6
F1
3
3
4
4
5
5
6
6
7
7
8
8
F2
2 1 3
HMQC 600 MHz
ppm
20
20
O S
40
C
4
5
1 2
60
3
6
7
40
8
60
cyclopropyl(thiophen-2-yl)methanone C8H8OS Mol. Wt.: 152
F1
78
6
80
80
100
100
120
120 2 3 1
8
7
6
5
4
F2
3
2
1
ppm
CHAPTER 8 ASSIGNED PROBLEMS
IR
164
121
70
80
90
100
m/z
110
120
130
149
136
103
91
77
50 60
140
150
160
3
6
3940
3920
2000 Wavenumber (cm-1)
7
Hz
3880
663 764
3000
1265 1412 1473 1550 1612
2962
50
H NMR 600 MHz
949
2870
3201
%Transmittance
100
4000 1
Problem 8.38A
100 65
% of Base Peak
MASS
1000
5
3860 Hz
9 10
8
Hz
3720
Hz
1280
320
Hz
300
OH
9 13
8
7
6
5
4
C/DEPT NMR 150.9 MHz
2
5
171.5
3
10
150
140
130
120
CH3
9
9
β-Thujaplicin C10H12O2 Mol. Wt.: 164
537
171.0 ppm
160
OH
4
H 3C 8
1
4
170
ppm
1
1
6
6
2
O 7
2
3
110
100
90
80
70
10
8
60
50
40
30
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.38B
ppm
1 2
7
6
ppm 6.8
5
6.6
6.4
4
3
6.2
2
1
ppm
ppm
9 10
1
6.2
O
5
2
7
8
6.4
1 2
6
7
3
3
36
6.6
F1
COSY 600 MHz
3
5
4
4
4
H 3C 8 10
5
5
6
6
7
7
CH3 9
β-Thujaplicin C10H12O2 Mol. Wt.: 164
F2
HMQC 600 MHz
ppm 20
20 9 10 ppm
40
40 7 3 5
125
60
8
60
130
F1 80
80
135
6 140
100
6.8
6.6
6.4
100
ppm
6.2
120
120
140
140 7
6
5
4
F2
OH
3
2
1
ppm
7 3 5 6
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.38C
INADEQUATE 600 MHz INADEQUATE 150.9 MHz 4
9 10
8
Hz -20000
-20000
-15000
-15000
-10000
-10000
-5000
-5000
F1
0
0
5000
5000
10000
10000
15000
15000
20000
20000 160 2 1
140
120 4
100
80
F2
60
6
5
40 3 7
20
ppm
Hz 0
0
5000
5000
F1 10000
10000
15000
15000
O 7
1 2
6
OH
20000
20000 5
175
170
165
160
155
3 4
H C 8 CH3 150 3 10 145 140 135 9
F2 β-Thujaplicin
C10H12O2 Mol. Wt.: 164
130
125
120
115
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.39A
% of Base Peak
MASS
123
100
83 55
41
50
151 69
95
232 230
110
50
100
4000
3000
150
m/z
200
IR 1034
1219 1365 1442 1473
80 70
1751
1
90 2954
%Transmittance
100
2000 Wavenumber (cm-1)
1000
10
H NMR 600 MHz 8
2800
Hz
1350
1300
1250
1200
1150
1100
1050
4
3
4.5
4.0
3.5
3.0
C/DEPT NMR 150.9 MHz
H3 C
7
5
900
5
6
2.0
Hz
850
6
ppm
1.5
CH3 4
5 6
950
8
9 13
2.5
1000
9
1
2
3
Br
CH3 O 3-Bromocamphor C10H15BrO Mol. Wt.: 230 10
8
2
20.0
200
180
19.9
160
9
19.8
140
ppm
120
3
1
100
80
60
6
4
5
10
7
40
20
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.39B ppm 5.0
F1
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
1.0
1.0
1.5
1.5
2.0
2.0
2.5
2.5
3.0
3.0
3.5
3.5
4.0
4.0
4.5
4.5
F2
COSY 600 MHz
9
10
8 6 6 5 5 4
3
HMQC 600 MHz
ppm 8
9
10
H3 C
7
4
5
20 6
1
3
2
CH3 O 3-Bromocamphor C10H15BrO Mol. Wt.: 230
F1
20
89 5
30
6
Br
10
30
10
10
CH3
40
40
7 50
4
50
3 1 60
60 5.0
4.5
4.0
3.5
3.0
F2
2.5
2.0
1.5
1.0
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.39C
INADEQUATE 150.9 INADEQUATE 600MHz MHz 13
2 Hz
-20000
-20000
-15000
-15000
-10000
-10000
F1 -5000
-5000
0
0
5000
5000
200
1
180 3
160 4
140
120
7
100 6
F2
80
60
40
ppm
20 10
5
Hz
-25000
-25000
-24000
-24000
-23000
-23000
-22000
-22000 8
9
F1
H3 C
-21000
7
4
5
-20000 1
6
CH3
2
-21000 3
Br
CH3 O 3-Bromocamphor C10H15BrO Mol. Wt.: 230
-19000
10
-18000 -17000 60
55
50
45
40
35
F2
30
25
20
15
10
5
-20000 -19000 -18000 -17000 ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.40A
% of Base Peak
MASS
FM (found) = 154.1351 154
108
100
81 71
139
111
93
55
50
136
50
60
70
80
90
m/z
IR
100
110
120
130
140
150
841 1080 987
4000 1
1219
1373 1466
50 2970
%Transmittance
100
3000
2000 Wavenumber (cm-1)
H NMR 600 MHz
1000
8,9
10
4,6 3,7 3,7
4,6 2
2.1
2.0
1.9
1.8
1.7
1.6
1.5
1.4
1.3
1.2
1.0 ppm
1.1
13 13
C/DEPT MHz C/DEPT NMR NMR 150.9 600 MHz 6
10
CH3
7 4 3
5 2
1
O CH3 8
9 CH3
1
75
Cineole C10H18O Mol. Wt.: 154
5
70
4,6
65
60
55
50
8,9 10
2
45
40
35
3,77
30
25
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.40B
ppm 2.2
2.0
1.8
1.6
1.4
1.2
1.0
ppm
1.0
1.0
1.2
1.2
1.4
1.4
1.6
1.6
1.8
1.8
2.0
2.0
COSY 600 MHz 10
8,9
2 3,7
4,6
F1
1
4
5
4,6
3,7
6
F2
HMQC 600 MHz
ppm
22
22 3,7 7 10
24 6 5
26 4
3
24
CH3 1 O 2
26 CH3
10
8
F1 28
9 CH3
28
Cineole C10H18O Mol. Wt.: 154
30
8,9
30 4,6
32
32 2
34
34 2.2
2.0
1.8
1.6
F2
1.4
1.2
1.0
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.41A
MASS % of Base Peak
82
CI Reagent gas methane
67
100
155 54
FM (found) = 155.0711 by CI
100
50 110
50
183
100
m/z
IR
50 160
195
170 180 m/z
190
903
1219
1790
4000 1
1450
50
1859
2862 2947
%Transmittance
100
3000
H NMR 600 MHz
3
2000 Wavenumber (cm-1) O
4
2
1000
4
2 1
O
3
O 1,2-cyclohexanedicarb oxylic acid anhydride C8H10O3 Mol. Wt.: 154
3.3 3.2 3.1 3.0 2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4
ppm
13 13
C/DEPT NMR NMR 150.9 600 MHz C/DEPT MHz
2 3
4
1
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.41B
ppm
3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2
1.5
ppm
COSY 600 MHz
4
1.5
3
2.0
2.0
2.5
2.5
3.0
3.0
F1
F2
2
HMQC 600 MHz
ppm 4 3
25
25
3
30
4
O 2
30
1
O
F1 35
O 1,2-cyclohexanedicarb oxylic acid anhydride C8H10O3 Mol. Wt.: 154
35
40
40
45
45 ppm
3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2
F2
2
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.42A
MASS % of Base Peak
104
100 121
50
131
91
77
164
65
50
146
60
70
80
90
100 110 m/z
IR
130
140
150
160
5 6
100
1
8
OH
10
1720
9
50
OCH3
6 7
4400
4350
1000
10
5
Hz
2750
2700
Hz 2000
1950
Hz
1650
1
7.0
6.5
748
2000 Wavenumber (cm-1)
H NMR 600 MHz 8
972
3000
1-methoxy-2-indanol C10H12O2 Mol. Wt.: 164
1088
4000
1350 1466
2831 2939
3402
%Transmittance
3 2
4 7
1
120
6.0
5.5
5.0
1600 Hz
2
3
4.5
4.0
3.5
OH
3
3.0
ppm
13 13
C/DEPT NMR NMR 150.9 600 MHz C/DEPT MHz
9
4
6
8
7
5
2
1
3 10
140
130
120
110
100
90
80
70
60
50
40
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.42B
ppm 7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
ppm
COSY 600 MHz 3
5
3.0
3.0
6 4
3.5
7
9
1
8
4.0
3
3 2
3.5 OH
F1
4.5
1-methoxy-2-indanol C10H12O2 Mol. Wt.: 164
5.0
10
4.0
10
OCH3
4.5
OH
2 1
5.0
5.5
5.5
6.0
6.0
6.5
6.5
7.0
7.0
F2
5 7 6 8
HMQC 600 MHz
ppm 3
40 ppm
40 58
126
60
7
10
60
128
6
130 7.4
80
7.3
7.2
ppm
2
80 1
F1 100
100
120
120
7.5
7.0
6.5
6.0
5.5
5.0
F2
4.5
4.0
3.5
3.0
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.42C 8
7
6
5
10 1 2
ppm
7.5
7.4
HMBC 600 MHz
7.3
7.2
7.1 ppm
4.5
3
4.0
3.5
OH
3.0
40
3
ppm ppm 3
40 5
50
50
6 4 7
F160
9 8
1
3 2
10 OH
60
10
OCH3 1-methoxy-2-indanol C10H12O2 Mol. Wt.: 164
70
70
80
80
90
90
2
1
F1 ppm
ppm
125
125
130
130
135
135
140
140
145
145 ppm
7.5
7.4
7.3
7.2
7.1 ppm
F2
4.5
4.0
3.5
3.0
5
6
94
8 7
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.43A
% of Base Peak
MASS
x 30
43
100
131
85
109
95
182
185 200
50 50
100
IR
150
m/z
200
100
HO
3000
H NMR 600 MHz 6
7
2000 Wavenumber (cm-1)
10
8
1000
11
Ethyl 3-hydroxy-3,6dimethylhept-6-enoate C11H20O3 Mol. Wt.: 200
8
9
1260
1240
Hz
780
740 Hz
760
4
2
7
OH
4.5
887
O4000
1034
10
1188
9
1373 1458
1
O
1 C
1728
5
70 2978
H3C 3 11 4
2
80
3518
%Transmittance
90
4.0
5
3.5
3.0
2.5
2.0
ppm
1.5
13 13
C/DEPT MHz C/DEPT NMR NMR 150.9 600 MHz
7
9
2
4
5
8
3 1
170
6
160
150
11
140
130
120
110
100
90
80
70
60
50
40
30
10
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.40A
ppm 5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.5
F1
ppm
1.5
2.0
2.0
2.5
2.5
3.0
3.0 6
3.5
3.5
4.0
COSY 600 MHz 11 10 4
8
5 2
OH
4.0 9
4.5
4.5 7
F2
HMQC 600 MHz
ppm 10
20
20
8
11
40
40
60
60
H3C 3 11 4
F1 100
1 C
2 5
O
9
10
O
7
80
7
120
8
Ethyl 3-hydroxy-3,6dimethylhept-6-enoate C11H20O3 Mol. Wt.: 200
140
9
100
6
120
160
140
6
160 1
5.0
4.5
4.0
3.5
3.0
F2
2
3
HO
80
5 4
2.5
2.0
1.5
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.43C
HMBC 600 MHz 8
9
7
OH
2
5
10
11
4
ppm 10
20
8 11
30
5 4
40
2
50 9
60 70
3
F180 F1 HO
90
H3C 3 11 4
100
1 C
2 5
O
9
10
O
7
6
110
7
8
Ethyl 3-hydroxy-3,6dimethylhept-6-enoate C11H20O3 Mol. Wt.: 200
120 130 140
6
150 160 170
1
5.0
4.5
4.0
3.5
F2
3.0
2.5
2.0
1.5
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.44A
MASS % of Base Peak
121
100 136
50
93
65
178
149
50
100
IR
150
m/z
50
H NMR 600 MHz
2000 Wavenumber (cm-1)
841
1
3000
1173 1211 1281
4000
1597 1658
2962
3325
%Transmittance
100
1000
9
3 7
2
8
6 OH
8.0 7.8 7.6 7.4 7.2 7.0 6.8 ppm
3.0
2.5
2.0
ppm
1.5
13 13
C/DEPT MHz C/DEPT NMR NMR 150.9 600 MHz
6
O 5
8 7
9
1 2 3 4
2 5
200
4
180
160
3 1
140
120
OH 4'-Hydroxy valerphenone C11H14O2 Mol. Wt.: 178
100
80
60
6
40
8 7
9
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.44B
ppm
8
7
6
5
4
3
2
1
1
ppm
COSY 600 MHz 9
1 6
O
2
5
8
8 7
7
2
9
1 2
3
6
3
3
F1
4
4
4
OH 4'-Hydroxy valerphenone C11H14O2 Mol. Wt.: 178
5
5
6
6 OH
7
7
8
8
F2
3 2
HMQC 600 MHz
ppm 9
20
20
8 7
40
40
60
60
F1 80
80
100
100
6
3
120
120 2
8
7
6
5
F2
4
3
2
1
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.44C
HMBC 600 MHz
3
2
7
6
8
9
OH
ppm
8.0
7.5
7.0
ppm
3.0
2.5
2.0
1.5
1.0
15
ppm ppm
9
15 6
O 5
20
8 7
9
20
1
F1
2
8 3
25
25
4
30
7
OH 4'-Hydroxy valerphenone C11H14O2 Mol. Wt.: 178
30
35
35 6
ppm
ppm
120
120
130
130
3
1 2
140
140
150
150
160
160
170
170
180
180
190
190
200
200
210
210 ppm
8.0
7.5
7.0
ppm
F2
3.0
2.5
2.0
1.5
1.0
4
5
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.45A
MASS % of Base Peak
68
100 108 53
50
79
0
50
153 151
125
93
100 m/z
IR
168
150
50
7 3
887 933
H NMR 600 MHz
1242
2000 Wavenumber (cm-1) 5,4 7 4
1412 1442
1
1705
3000
2669
2893 2962 3078
%Transmittance
100
1000
5 10
1 2900
Hz
2850
1600
1550
x64
Hz
1200
1150
1100
Hz
1050
9
OH
ppm
12
4.5
4.0
3.5
3.0
2.5
2.0
1.5
7
5 10 4 1
ppm
9 C/DEPT MHz C/DEPT NMR 150.9 600 MHz H2CNMR
13 13
H
3 1 7 8
HO
4
2 6
5
CH3
10
O 2-((1R,2S)-1-methyl-2-(prop-1-en-2yl)cyclobutyl)acetic acid C10H16O2 Mol. Wt.: 168 8
9
3
6
2
180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.45B
5.0
ppm
4.5
4.0
3.5
3.0
2.5
2.0
1.5
COSY 600 MHz
ppm
10
1.5
1.5
2.0
2.0
2.5
2.5
54 5,4 7
1
7 3
F1 3.0
3.0
3.5
3.5
4.0
4.0
4.5
4.5 9
5.0
5.0
F2
HMQC 600 MHz
ppm 20
9
H2C
3
40
20
H 4
2
1 7 8
HO 60
40
5
6
3
CH3
60
10
O 2-((1R,2S)-1-methyl-2-(prop-1-en-2yl)cyclobutyl)acetic acid ppm 80 C10H16O2 Mol. Wt.: 168
F1
100
20
120
30
140
80 1 10
100 120 140
40
160
160 50
180
180 3.0
5.0
4.5
4 1 10 5 7
4.0
3.5
2.5
3.0
F2
2.0
2.5
1.5
2.0
ppm
1.5
ppm
9
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.45C
HMBC 600 MHz 9
1 3
5.0
ppm
4.8
ppm
7
2.6
7 2.4
2.2
5,4
2.0
4 1.8
10
5 1.6
1.4
1.2
ppm
4 20
1 25 9
H2C 30
10 H 3
4
5
2
1 7 8
HO 35
5
6
CH3
10
O F1 2-((1R,2 S)-1-methyl-2-(prop-1-en-2yl)cyclobutyl)acetic acid C10H16O2 40 Mol. Wt.: 168
7 6
45
50
3
9
ppm
2
150
8 5.0
4.8
ppm
2.6
2.4
F2
2.2
2.0
1.8
1.6
1.4
1.2
ppm
CHAPTER 8 ASSIGNED PROBLEMS % of Base Peak
100 50 53
IR
91
77
122
65
50
60
70
80
90
100
110 m/z
120
151 148
133
130
140
166
150
160
787
1365 1466
%Transmittance
100
50
2916
1049
3332
4000 1
Problem 8.46A
105
MASS
3000
H NMR 600 MHz
2000 Wavenumber (cm-1)
1000
10 4
2180
2160 Hz
1440
9
1420
1400
1380
5
9
1360
1340
1320
1300
1280
1
1260
1240
1220 Hz
8
7 3
11
5.0 13
4.5
4.0
4
OH
3.5
3.0
2.5
2.0
1.5
ppm
1.0
C/DEPT NMR 150.9 MHz 10 11
CH2CH2OH 2 1
3 8
6
9
7 4
5
3
130
120
1
Nopol C11H18O Mol. Wt.: 166
2
140
11
110
100
90
80
5 10
9
4 7
8
6
70
60
50
40
30
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.46B
ppm 5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
COSY 600 MHz
ppm
8
1.0
1.0
1.5
1.5
2.0
2.0
4 7 5 10
2.5
2.5
4 9
F1 3.0
3.0
3.5
3.5
4.0 2 4.5
4.0
5.0
5.0
5.5
5.5
1 OH
11
4.5
F2
3
HMQC 600 MHz
ppm 10 11
20
8 7
20
CH2CH2OH 2 1
40
3 8
6
9
40
7
6
4
1
5
Nopol C11H18O Mol. Wt.: 166
60
F1
ppm 30
80
11
60
4 9
80
6 10 5
100
35
100 40
120
2.5
5.5 2 OH
5.0
4.5
4.0
3.5
2.4
3.0
F2
2.3
2.2
2.5
2.0
2.1
1.5
ppm
1.0
120 ppm
3
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.46C INADEQUATE MHz INADEQUATE 150.9600 MHz
2
3
1
11
Hz -15000
-15000
-10000
-10000 10 11
-5000
-5000
CH2CH2OH 2
F1
1
0
6
9
5000
0
3 8
7 4
5000
5
Nopol C11H18O Mol. Wt.: 166
10000
10000
15000
15000 140
1
130
120
5
110 10
100
6
90
F2
80
70
9 4
60 7
50
40
30
20
ppm
8
Hz -16000
-16000
-14000
-14000
-12000
-12000
-10000
-10000
-8000
-8000
-6000
-6000
F1 -4000
-4000
-2000
-2000
0
0
2000
2000
4000
4000 45
40
35
F2
30
25
20
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.47A
% of Base Peak
MASS
105
CI Reagent gas methane
100
277
100 77
50
136 154
50
FM (found) = 277.1083 by CI
100
150
IR
50 200
m/z
305
250
m/z
317
300
2877 2939
1
3000
H NMR 600 MHz 3
2
1281
1712 1751
4000
2000 Wavenumber (cm-1)
6
1000
9
12
10
4
4800
4700
4600
717
50
1072
3456
%Transmittance
100
7
10
OH
4500 Hz 3300
3200 O
3100
3000 Hz
1500
11
1400
Hz
1300
8 12
O 13 9
O 10
CO
12 8
6
O C O 5 1
7
O O
CH2OH
11
2200 Hz
2250
1750
1700 Hz
3.0
2.5
2 HOH 2C 4
3
5-(Benzoyloxy)hexahydro-4(hydroxymethyl) C15H16O5 Mol. Wt.: 276
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.47B
ppm 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5
ppm
COSY 600 MHZ 7
O O 13 9
3
10 6
O C O 5
41
3
12 8 7
11
CH2OH
4
11
2 4
3
5
5
F1 5-(Benzoyloxy)hexahydro-4(hydroxymethyl) C15H16O5 Mol. Wt.: 276
6
9 6
6 O C
7
O O
O
7 3
4
HOH2C
8
2
8
COSY 600 MHZ
ppm
7
2.5
2.5
3.0
3.0
3.5
3.5
10 12
10 12 8
11
F1 4.0
4.0
4.5
4.5
5.0
5.0
5.5
5.5 5.5
5.0
4.5
4.0
3.5
F2
3.0
2.5
ppm
9 6
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.47C 13
C/DEPT NMR 150.9 MHz
2 3
1
13 180
170
160 3
2
9
129 ppm
130
5
4
150
140
77.5
130
4
6
11
8 1012
7
ppm
77.0
120
6
110
100
90
80
70
40 ppm
50
HMQC 600 MHz
11
9
60
7
ppm O
40
O 13 9 10
50
C O 5
60
1
O
12
O 7
13
O
7
OH HOH2C
CH2OH
11
11 13
2
70 4
C
8 6
O
12 8 10
O
3
6
F1805-(Benzoyloxy)hexahydro-4(hydroxymethyl) C15H16O5 Mol. Wt.: 276
12 8
90
ppm
100
35
12
10
9
10
12 10 8
110 40
120 3.0
2.9
2.8
2.7
2.6
2.5
2.4
3
ppm
130
2 4 8.0
7.5
7.0
6.5
6.0
5.5
5.0
F2
4.5
4.0
3.5
3.0
2.5
ppm
CHAPTER 8 ASSIGNED PROBLEMS Problem 8.47D
HMBC 600 MHz
2 4
ppm
8.2
8.0
7.8
3
7.6
40
6
7.4 ppm
11
9
5.0
4.5
4.0
12 8
3.5
3.0
10 7 OH
2.5
ppm
12 10 8
O O 13 9 10
50
6
O C
5 O
60
1
12 8 7
7
CH2OH
11
11
2 4
70
3
5-(Benzoyloxy)hexahydro-4(hydroxymethyl) C15H16O5 Mol. Wt.: 276
6
80
9
F1 ppm
3 2
1
130
4 140
150
160
5 170
13 180 8.2
8.0
7.8
7.6
7.4 ppm
5.0
F2
4.5
4.0
3.5
3.0
2.5
ppm
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