Isomerism Ans
February 19, 2019 | Author: HarshitShukla | Category: N/A
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ORGANIC CHEMISTRY
Answers for Isomeris DPP ( Conceptual Improvement of Isomerism ) Q.1(a) (f) (k) (p) Q.2(a) (f) Q.3
Identical (b) Position (g) Functional (l) Chain (q) Metamers (b) Functional (g) A-Q, B-Q, C-R, D-S
Position (c) Chain Functional Ring chain Identical Functional
1. 5. 8. 11. 13. 17. 21.
Position isomers Identical Functional Ring chain Position isomers Chain Identical
2. 6. 9. 12. 14. 18. 22.
1. 8. Q.15
C B D
2. 9.
D B
Answers of DPP No. – 1 Position (d) Functional (e) Position (h) Position (i) Position (j) Functional (m) Functional (n) Functional (o) (r) Chain (c) Metamers (d) Metamers (e) (h) Metamers
Answers of DPP No. – 2 Metamers 3. Positional Functional 7. Functional Non-identical 10. Non-identical Non-identical / homologous Chain isomers 15. Position Position 19. Position 20. Functional
3. 10.
Answers of DPP No. – 3 4. B 5. C Q.11 D Q.12 C
B C
Q.16.
1°
2°
2°
2°
(a) (1°,2°,3°) CH3 — CH2 — CH2 — CH2
2°
1°
CH2 — CH3 (b)
2°
3°
3°
4-ethyl-3-methyloctane
2°
(c) (1°,2°,3°, 4°)
2°
3°
1°
(5) DBE = 1
3°
2° 3° 3°
1°
A C
C C
2°
7. Q.14
CH3
(1°,2°,3°)
2°
CH3
CH
1° 3 1° 1,2,7-trimethylcyclopentadecane
1°
1° 4° 2°
1°
3°
(d) (1°,2°,3°, 4°)
2° 2°
2° 3°
CH3
1° 1,1,2,5-tetramethylcyclopentane
Q.17
Metamers
2°
1°
CH3 3° 1° CH3 4° CH3
16. Identical
2°
2° 2°
Chain
1°
2°
2°
CH3 — CH2 — CH — CH — CH3
1°
2°
Functional
4.
6. Q.13 2°
2°
Functional
CH2 = CH — CH2 — CH3,
CH3 1°
CH3 — HC = CH — CH2,
,
,
CH3 — C = CH2 CH3
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1
OH O Q.18
DBE = 1 (5)C3H6O
CH3 — C — CH3 ,
,
CH3 — CH2—C H
Q.19
,
O
CH2 = CH — O — CH3 CH2 = CH — CH2 — OH, (5) DBE = 1 CH3—CH2—CH2—HC=CH2, CH3—CH2—HC=CH — CH3,
CH3 — CH2 — CH = CH2 , CH3
CH3—CH=C—CH3 ,
,
CH2=CH—CH—CH3 ,
CH3 Q.20
CH3 — CH2 — C ≡ CH, CH3 — C ≡ C — CH3,
(9) DBE = 2 C4H6 CH3 — CH = C = CH2,
,
,
(4)
,
,
O
O Q.21
,
CH3
C — CH2 — OH,
CH2=CH —CH = CH2,
,
O
CH3 — C
,
O
H — C — O — CH3 ,
OH
O—H
H
,
Answers of DPP No. – 4 Q.1(a) Position (b) Position (c) Position (d) Position (e) Chain (f) Position (g) Position (h) Position (i) Position (j) Chain (k) Position Q.2(a) 7 (b) 3 (c) 4 (d) 2 (e) 4 Q.3 (a) π = 2, σ = 30 (b) π = 5 σ = 17 (c) π = 3 σ = 34 (d) π = 4 σ = 27 (e) π = 4 σ =3 (f) π = 2 σ = 5 (g) π = s2 σ = 7
Et Et Q.4
A
Q.5
C
Q.6
C
Q.7
D
Q.8
H CH3
CH3 CH3
Br Q.9
CH3–CH2–CH2–Br
H
H
H
H
H Q.10
CH3 — CH — CH3
Cl Q.11
Cl
H
H
,
H
H
H
H
(anti)
(b) 1, 2
H C
Q.13
Q.15
a>c>b
A
H H
Cl
H (a) (gauche)
Q.12
CH3
CH3
CH3
H
Cl Q.14
0.75 D = 0.3 X µgauche
µgauche =
7.5 = 2.5 D. 3 CH3
Et H Q.16
CH3—CH2—CH—CH2—CH3 (a) CH3
C2H5
H (b) CH3—CH 2—CH—CH 2—CH 2—CH 3
H
CH3 CH3
CH3
H
H
C2H5 H
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2
+ N(Me)3
O–H O C—H
H
O
H
Q.17
O C
H
H
H
T↑
Q.20
Q.19
CH3 O
H
H
H
H
H
µ↑
CH3 Q.21
N H
H
H
CH3 CH3
H
CH3
Q.18
(a) gauche
(b) anti
Q.22
CH3
H
H
CH3
H
(a)
CH3
Et H
CH3
H
(b)
(c)
CH3
H
CH3
H
CH3
CH3
CH3
Ph
Ph
H
CH3
H
CH3 (d)
(e)
H
H
CH3
CH3 CH3
Ph Q.23
(a) i > ii > iii
(b) i > ii > iii
Q.1 Q.5
(a) 120° (b) < 109°28 E
1
(c) 0°
(c) 3 > 2 > 1 > 4 (d) i > ii > iii (e) i > ii Answers of DPP No. – 5 (d) 60° Q.2 C Q.3 B
Q.4
D
Keq = 18 x
100-x
100 − x = 18 x
Q.6
18 × = 100 – x 19 × = 100 X = 100/19 C Q.7 D
H
O C
H
Q.8
C
H O
Q.13
Q.14
H
H
Q.9
Q.10
B
+1
+1
+1
E
C/A
B/D/F
Anti
H
B
All Gauche All eclipsed
Q.11
A, B, D Q.12
+1
B
+1
B
E
Highest in energy
Lowest in energy
F Q.15
F x
Keq = 1.5
100-x
100 − x = 1.5 x 1.5 × = 100 – x 25 × = 100 X= Q.16
100 ×10 25
= 40% C
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3
Q.1 Q.4
A – P, R; B – Q, S; C – P, R; D – Q, R Xanti = 3/4
Answers of DPP No. – 6 Q.2 (IV) > (III) > (I) > (II)
OH Q.5
Q.3
B
OH HO
(a)
and
HO OH
HO
(b)
and
OH
OH
(c)
and
(d)
and
(e)
and
(f)
and
(g)
and
(h)
and
Cl Cl Q.6
(a)
Cl Q.8
c>d>b>a
Cl Cl
Cl
Cl (b) Cl
Cl Cl
Q.9
(a)
(b)
Trans Q.1
Q.7
Cl
Cl
Cis
Cis
Answers of DPP No. – 7 (1) Z (2) Z (3) E (4) Z (5) Z (6) E (7) E (8) Z (9) Z (10) E (11) Z (14) E (15) Z (16) E (17) E (18) E (19) Z (20) E (21) Z (22) E (23) E (24) Z
Trans (12) Z (13) E
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4
Z
Z (25) Z
(26) Z
Z
Z
Q.2
(1) (A) X
(B) X
(C) √
(D) X
(2) (A) X
(B) √
(C) √
(D) X
(3) (A) Cis (H) Trans
(B) Trans (I) Cis
(4) (A) X
(B) X
1
3
3
Q.2 Q.4
Q.5 Q.1 Q.6 Q.8
A D (A) √ (N) √ B
Q.9
(28) E
(E) √
(C) Cis (J) X
(C) √
(F) √
(D) Cis (K) Trans
3
2
(F) Cis
(G) Trans
Answers of DPP No. – 8 2 3–1 (3–1)/2 3–1 (3–1)/2 3 (6) 2 (7) 2 +2 =6 (8) 2 + 2 =6 (9) 2 1 1 1 1 1 1 4 (12) 2 (13) 2 (14) 2 (15) 2 (16) 2 (17) 2 (18) 2 1 2 1 3 (21) 2 (22) 2 (23) 2 = 4 (24) 2 (25) 2 (26) 2 (27) 2 1 (33) 2
Answers of DPP No. – 9 2 3 1 1 Q.4 (A) 2 (B) 2 (C) 2 (D) 2 (E) 2 (F) 2
C Q.3 (A), (B) (C) X (D) √
D (E) √
(F) X
(G) √
Q.10
B
B
Q.12
(A) = Keq < 1
Q.11
(E) Trans (L) Cis
(D) √
Q.2 Q.7 (B) √
Compound
(29) Z
Z
(2) 2 (3) 2 (4) 2 (5) 2 (1) 2 2–1 2/2–1 1 (10) 2 + 2 =2+1=3 (11) 2 3–1 (3–1)/2 3 =6 (20) 2 = 8 (19) 2 +2 2 2 2 2 (28) 2 (29) 2 (30) 2 (31) 4 (32) 2 Trans Q.3 Trans 3–1 (3–1)/2 =6 (A) 2 + 2 1 (B) 2 = 2 1 (C) 2 = 2 2 (D) 2 = 4 1 (E) 2 = 2 B, C Q.6 B
Q.1
(27) E
Z
(H) √
(I) √
(J) X
(B) Keq = 1
Answers of DPP No. – 10 P.O.S.
(K) √
Q.5
A,B,C
(L) √
(M) √
(C) Keq > 1
(D) Keq = 1
C.O.S.
Optically active
X
X
1.
CH3 H
CH3
√
H
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5
2.
H
CH3
CH3
H
X
X
√
√
X
X
√
X
X
√
X
X
√
√
X
X
X
√
√
X
X
X
X
√
X
X
√
H
3.
H CH3 CH3 H
H 4.
5.
CH3
CH3
H
H Cl
Cl 6.
H
Cl
Cl
H
Br
7.
H
Cl Cl H
Cl H
8.
Cl H
H Cl
Cl 9.
H Cl
10. H
Cl
C=C=C
H Cl
C=C=C
Cl Br
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6
11. H
Cl 12.
H Cl
13.
14.
H
C=C=C=C
√
X
X
√
X
X
√
√
X
X
X
√
√
√
X
√
√
X
√
X
X
√
X
X
Cl
C
C
H Cl
Cl
H C
C H
Cl
H Cl
H Cl
H
15.
CH 3 CH3 H H Cl
16. Cl
H
17.
H 18.
C Cl
CH3
CH3
H
C
H
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7
19.
CH3
CH3
H
C
X
X
√
√
X
X
X
X
√
X
√
X
√
√
X
√
X
X
√
X
X
X
X
√
X
X
√
√
X
X
Cl
20.
21.
Cl
22.
I
I
Cl
23.
24. O = C = O 25.
26.
O=C=O H
H
O=C=O
H
27.
N=N=N H
H
H C
28.
H
H
No. of POS = 4C2 = 6
H
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8
H C
29.
Cl
H
No. of POS = 3
X
√
X
X
√
√
X
H C=C
CH3
No. of POS = 2
CH3
CH3 31.
X
H
H 30.
√
H C=C
H
No. of POS = 1
CH3
Answers of DPP No. – 11 Q.1
(i) 2 (ii) 3 (iii) 4 (iv) 10
Q.3
(d) 3 > 1 > 2 > 4 (a) R (b) R (c) S (n) R (o) S (p) S
Q.4
(a) R (b) R (n) T (o) S (v) R, S
Q.2
(a) 1 > 3 > 2 > 4
(b) 2 > 1 > 3 > 4
(e) 3 > 1 > 2 > 4 (f) 4 > 2 > 3 > 1 (d) S (e) R (f) S (g) R (h) S (i) S (q) R, R (r) R, R (s) S, R
(c) S (d) S (e) R (p) S (q) R,R (w) R, S
(f) S (g) R (r) S,R (x) R, S
(h) S (i) S (s) S, R (y) R, R, R
(c) 2 > 1 > 4 > 3
(g) 4 > 3 > 2 > 1 (j) S (k) S (l) R (m) S (t) R, S (u) R, S (j) S (k) S (t) R, S (z) R
(l) R (m) S (u) R, S
Answers of DPP No. – 12 Q.1 Q.3 Q.6 Q.7 Q.14
A → Q; B → Q; C → R,S; D → Q; Q.2 A → T,P,S; B → T, P; C → S; D → Q; B Q.4 Q.5 D A-B = Enantiomer, C-D = Enantiomer, A-C, A-D = distereomers, B-C & B-D = disteromers A Q.8 8 Q.9 5 Q.10 Q.11 C Q.12 Q.13 (a) 4 (b) 4 (c) 7
Q.1 Q.3 Q.10 Q.14
A → S,P; B → Q; C → S,P; D → S,R; A Q.4 C Q.5 A Q.6 Q.11 A, B, D Q.12 (a) diastereomers (b) distereomers (e) enantiomers (f) distereomers No-sym. Present (i) optical isomers = 27 = 128. (ii) optically active = 2n = 27 = 128 (iii) meso = 0
Answers of DPP No. – 13
Q.15
(iv) Q.1
enantiopair
A → Q, R;
A → T; B → S,R; C → P; D → T; Q.7 A Q.8 C Q.9 Q.13 4 (c) distereomers (d) distereomers Q.2 A
D
2n 128 = = 64. 2 2 Answers of DPP No. – 14
B → S, R, T; C → Q, R, T; D → P, Q;
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Q.2 Q.3 Q.7 Q.8
A → P, R; B Q.4 α = 125° (A) chiral (H) achiral
B → S; D Q.5
C → P, R, S; D → Q; B Q.6 (A) X (B) X (C) √
(B) achiral (I) chiral
(C) achiral (J) chiral H N: *
(a) – 12.5°
(b) + 8.6°
(E) chiral (L) chiral
(F) achiral (M) achiral
(G) chiral
(v) achiral
(vi) achiral
(vii) chiral
H
* *
Q.9
(D) achiral (K) chiral
(D) √
N
O
(c)
O COOH
Q.10
(i) achiral (viii) chiral
(ii) achiral (ix) achiral
(iii) chiral
(iv) chiral
Answers of DPP No. – 16 1.
Diastereomer
2.
Identical (a & b); Diasteromer (a & b ; b & c)
3.
Diastereomer
4.
Diastereomer
5.
Identical
6.
Identical
7.
Identical
8.
Consitutional Isomer 9.
Diastereomer
10.
Enantiomer
11.
Enantiomer
12.
Diastereomer
Constitutional isomer 14.
15.
Constitutional isomer
13.
Consitutional isomer
Answers of DPP No. – 17 1.
Constitutional isomer 2.
Constitutional isomer 3.
Constitutional isomer 4.
Enantiomer
5.
Enantiomer
6.
Enantiomer
7.
Diastereomer
8.
Consitutional Isomer
9.
Identical
10.
Constitutional isomer
11.
Diastereomer
12.
Enantiomer
13.
Constitutional isomer
14.
Identical
15.
Diastereomer
Answers of DPP No. – 18 1.
Enantiomer
2.
Identical
3.
5.
Diastereomer
6.
Constitutional isomer
7.
Enantiomer (b & c); Diasteromer (a & b ; b & c)
10.
Constitutional isomer
11.
Constitutional isomer
12.
Constitutional isomer
13.
Constitutional isomer
14.
Identical
15.
Constitutional isomer
16.
Constitutional isomer
8.
Identical
4.
Diastereomer 9.
Diastereomer Identical
Answers of DPP No. – 19 1.
Constitutional isomer
2.
Constitutional isomer
3.
Constitutional isomer
4.
Constitutional isomer
5.
Constitutional isomer
6.
Constitutional isomer
7.
Other
8.
Constitutional isomer
9.
Other
10.
Other
11.
Constitutional isomer
12.
Constitutional isomer
13.
Constitutional isomer
14.
Constitutional isomer
15.
Enantiomer
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10
Answers of DPP No. – 20 C2
C : The C2 axis lies along the Intersection of the 2 vertical σ-planes.
1. N
2.
C2v C2 H
H C 3.
C2 D2d : 3 C2 axis with the 2σ planes intersecting the principle (vertical) C2 axis.
C C H
H
C2 D6h : There are 3 pairs of vertical σ planes (not shown) and of C2 axis
C6
4.
intersecting the C6 axis. The C atoms lie in the horizontal σ-plane. 5.
6.
P.O.S. (σ) ; C3
C2
7.
P.O.S.(σ) ; C2 ; C3 ; S4 ; S2
Answers of DPP No. – 21 1.
P.O.S. (σ) ; C2
2.
P.O.S. (σ) ; C2 ; C3 ; S4 ; S2
4.
P.O.S. (σ) ; C2
5.
P.O.S. (σ) ; C2
7.
C2
9.
C2
8.
C2
10.
6.
3.
P.O.S. (σ) ; C2
P.O.S. (σ) ; C2 ; S2
P.O.S. (σ) ; C2 ; S2
Answers of DPP No. – 22 S.NO. 1. 2. 3. 4. 5.
MESO 3 -
ACTIVE ISOMERS 2 4 8 16
TOTAL ISOMERS 5 4 2 8 16
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11
6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 15.
2 1 1 1 2 -
8 8 4 2 2 4 2 8 32 8
10 8 4 3 2 3 4 3 10 32 8
Answers of DPP No. – 23 S.NO. 1. 2. 3. 4. 5. 6. 7. 8.
MESO 1 1 -
ACTIVE ISOMERS 2 4 2 16 32 4
TOTAL ISOMERS 3 4 3 16 2 32 3 4
Answers of DPP No. – 24 S.NO. 1. 2. 3. 4. 5. 6. 7. 8. 9.
MESO 1 1 1 8
ACTIVE ISOMERS 2 16 16 16 2 2 2 4 128
TOTAL ISOMERS 3 16 16 16 3 2 3 4 136
Answers of DPP No. – 25 S.NO. 1. 2. 3. 4. 5. 6.
MESO 1 1
ACTIVE ISOMERS 16 2 8 8 2
TOTAL ISOMERS 2 16 3 8 8 3
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7. 8. 9. 10. 11.
8
4 4 2 2 128
4 4 2 2 136
Answers of DPP No. – 26
1. 4. 7. 10. 13. 16.
Optically active:- OA Chiral molecule:- CM Achiral molecule:- AM Optically inactive:- OI No. of chiral cente:- CC AM, Ol, CC = 1 2. OA, CM, CC = 0 3. OA, CM, CC = 1 OA, CM, CC = 1 5. OA, CM, CC = 0 6. AM, Ol, CC = 2 OA, CM, CC = 2 8. OA, CM, CC = 5 9. AM, Ol, CC = 2 AM, Ol, CC = 4 11. OA, CM, CC = 2 12. OA, CM, CC = 2 OA, CM, CC = 3 14. OA, CM, CC = 2 15. AM, Ol, CC = 2 AM, Ol, CC = 2
Answers of DPP No. – 27
1. 4. 7. 10. 13. 16.
Optically active:- OA Chiral molecule:- CM Achiral molecule:- AM Optically inactive:- OI No. of chiral cente:- CC AM, Ol, CC = 0 2. AM, Ol, CC = 0 3. AM, Ol, CC = 0 AM, Ol, CC = 2 5. AM, Ol, CC = 3 6. AM, Ol, CC = 0 OA, CM, CC = 0 8. AM, Ol, CC = 0 9. AM, Ol, CC = 0 AM, Ol, CC = 4 11. OA, CM, CC = 2 12. OA, CM, CC = 2 AM, Ol, CC = 2 14. AM, Ol, CC = 2 15. CM, OA, CC = 2 AM, Ol, CC = 2
Answers of DPP No. – 28
1. 4. 7. 10. 13. 16.
Optically active:- OA Chiral molecule:- CM Achiral molecule:- AM Optically inactive:- OI No. of chiral cente:- CC AM, Ol, CC = 0 2. OA, CM, CC = 0 3. OA, CM, CC = 1 OA, CM, CC = 2 5. OI, AM, CC = 0 6. AM, Ol, CC = 0 OA, CM, CC = 3 8. OA, CM, CC = 2 9. AM, Ol, CC = 0 AM, Ol, CC = 0 11. AM, Ol, CC = 2 12. OA, CM, CC = 0 AM, Ol, CC = 0 14. CM, OA, CC = 0 15. AM, Ol, CC = 0 CM, OA, CC = 0 17. CM, OA, CC = 2
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