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September 11, 2017 | Author: rachel | Category: Redox, Organic Chemistry, Chemistry, Physical Sciences, Science
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Chapter Thirteen Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Easy 1. What is the IUPAC name for the following compound? CH3

CH3

CH3CHCHCHCHCH3 OH

A) B) C) D) E)

CH3

4-isopropyl-3,4-dimethyl-2-butanol 2,3,4-trimethyl-4-pentanol 1,1,2,3-tetramethyl-4-pentanol 3,4,5-trimethyl-2-hexanol 3,4,5,5-tetramethyl-2-pentanol Ans: D

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Easy 2. A) B) C) D) E)

What is the IUPAC name for isobutyl alcohol? 2-methyl-1-propanol 2-methyl-1-butanol 1-methyl-1-propanol 1,1-dimethyl-1-ethanol 3-methyl-1-propanol Ans: A

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Easy

3. What is the IUPAC name for the following compound? CH2CH3

CH3CH2CCH2CH3 OH

A) B) C) D) E)

1,1,1-triethylmethanol 1,1-diethyl-1-propanol 2-ethyl-3-pentanol 3-ethyl-3-pentanol t-heptanol Ans: D

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 4. A) B) C) D) E)

What is the IUPAC name for t-butyl alcohol? 1-butanol 2-methyl-1-propanol 2-methyl-2-propanol 2-butanol 1,1-dimethyl-1-ethanol Ans: C

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 5. What is the IUPAC name for the following compound? OH

A) B) C) D) E)

1-isopropyl-4-cyclopentanol 3-isopropyl-1-cyclopentanol 1-isopropyl-3-cyclopentanol 1-isopropyl-4-hydroxycyclopentane None of these Ans: B

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium

6. What is the correct structure for 1-chloro-3-ethyl-2-pentanol? CH2CH3

CH2CH3

CH3CH2CCH2CH2Cl OH

A) B) C) D) E)

CH3CHCHCH2CH2Cl OH

I

II

CH3CH2CHCH2CHCl CH3CH2CHCHCH2Cl III

I II III IV None of these Ans: D

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 7. What is the IUPAC name for the following compound? Br

HO

A) B) C) D) E)

2-methyl-5-bromocyclohexanol 3-bromo-2-methylcyclohexanol 1-bromo-4-methylcyclohexanol 4-bromo-6-methylcyclohexanol 4-bromo-2-methylcyclohexanol Ans: E

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard

CH2CH3

CH2CH3

OH

IV

OH

8. What is the IUPAC name for the following compound? CH2CH2OH

CH3CH2C=CCH2CH3 CH3

A) B) C) D) E)

3-methyl-4-ethyl-3-hexen-6-ol 4-ethyl-3-methyl-3,6-hexenol 3-ethyl-4-methyl-3-hexen-1-ol 3-methyl-4-(2-hydroxyethyl)-3-hexene 3-(2-hydroxyethyl)- 3-methyl-3-hexene Ans: C

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 9. What is the IUPAC name for the following compound? OH

A) B) C) D) E)

4-penten-2-methyl-2-ol 4-methyl-1-penten-2-ol 2-methyl-4-penten-2-ol 4-methyl-1-penten-4-ol 4-hydroxy-4-methyl-1-pentene Ans: C

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 10. What is the IUPAC name for the following compound? CH3 H HO

C C CC H

2 CH 3

A) B) C) D) E)

(R)-3-hexyn-2-ol (S)-3-hexyn-2-ol (R)-2-hexyn-4-ol (S)-2-hexyn-4-ol (S)-2-hydroxy-3-hexyne Ans: B

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 11. What is the correct structure for 2,2-dibromo-1-methylcyclohexanol? OH Br

Br

Br

Br

CH3CCH2CH2CH2CHOH

CH3CH2CH2CH2CCH(CH3)OH I

Br

Br

II

OH

III

OH

Br

Br

Br

Br

IV

A) B) C) D) E)

CH3

V

I II III IV V Ans: D

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 12. What is the correct structure for (E)-5,5-dimethyl-3-hepten-1-ol? OH HO

I

III

II OH

HO OH

A) B) C) D) E)

I II III IV V Ans: E

IV

V

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 13. What is the IUPAC name for the following compound?

OH

Ans: 7-ethyl-8-methyl-4-nonanol Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 14. What is the IUPAC name for the following compound?

HO

Ans: (R)-3-ethyl-2-methyl-3-heptanol Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 15. What is the IUPAC name for the following compound? Br

OH

Ans: (1R,2S)-2-bromo-1-methylcyclopentanol Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard

16. What is the IUPAC name for the following compound? OH

Ans: 7-cyclohexyl-2,8-dimethyl-3-decanol Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 17. Provide the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol? Ans: OH

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 18. Provide the structure for 5-chloro-2-propyl-1-heptanol. Cl Ans:

OH

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 19. Provide the structure for 6-sec-butyl-7,7-dimethyl-4-decanol. Ans:

OH

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard

20. What is the IUPAC name for the following compound? OH

Ans: 4-isobutyl-2-methyl-3-octanol Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 21. What is the IUPAC name for the following compound? HO

H C

CH3(CH2)4

C C H

Ans: (S)-1-octyn-3-ol Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 22. What is the IUPAC name for the following compound? HO

Ans: 4,5,6-tripropyl-4-decanol Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 23. What is the IUPAC name for the following compound? HO

Ans: 3-ethyl-3-cyclohexen-1-ol

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Easy 24. What is the correct structure for 2-methylphenol? HO

A) B) C) D) E)

OH

OH

I

II

OH

OH

III

IV

V

I II III IV V Ans: A

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 25. What is the correct structure for 2-bromo-5-isopropylphenol? OH

Br

OH

OH

OH

Br

IV

V

Br

Br

Br

I

A) B) C) D) E)

I II III IV V Ans: B

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium

II

III

OH

26. What is the IUPAC name for the following compound? OH Br

Br

A) B) C) D) E)

3,4-dibromophenol 2,4-dibromophenol 2,5-dibromophenol 3,6-dibromophenol 2,6-dibromophenol Ans: C

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 27. What is the IUPAC name for the following compound? OH

Ans: 2-sec-butyl-5-ethylphenol Topic: Nomenclature of alcohols Section: 13.5 Difficulty Level: Medium 284. What is the IUPAC name for the following compound? HOCH2CH2CH2OH A) 1,2-butanediol B) isopropanol C) 1-propanol D) 1,3-propanediol E) 1,2-ethanediol Ans: D Topic: Nomenclature of alcohols Section: 13.5 Difficulty Level: Hard

295. What is the IUPAC name for the following compound? OH

OH

A) B) C) D) E)

cis-1,2-cyclopentanediol meso-1,2-cyclopentanediol (1R,2R)-1,2-cyclopentanediol (1R,2S)-1,2-cyclopentanediol (1S,2S)-1,2-cyclopentanediol Ans: E

Topic: Nomenclature of alcohols Section: 13.5 Difficulty Level: Hard 3026. What is the IUPAC name for the following compound?

OH

OH

Ans: 3,5-dimethyl-2,4-heptanediol Topic: Nomenclature of alcohols Section: 13.5 Difficulty Level: Hard 3127. Provide the structure for (2R, 3S)- 2-bromo-1,3-pentanediol. Ans:

OH

OH Br

Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Hard

3228. Explain why cyclohexanol has a pKa of 18 and phenol has a pKa of 10. Use structural drawings to explain your reasoning. Ans: The conjugate base of phenol is resonance stabilized. The negative charge on oxygen is delocalized over the aromatic ring. This makes the conjugate base more stable and thus a weaker base, making phenol a stronger acid. O

O

O

O

The conjugate base of cyclohexanol has no resonance stabilization and the negative charge on oxygen is localized, making it a stronger base, and cyclohexanol a weaker acid O

Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium 3329. Rank the following alcohols in decreasing order of acidity.

Br

I

Ans: II>I>III Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium

OH

OH

OH

F

II

I

III

340. Which one of the following alcohols is most acidic? O

OH

O

OH

OH

III

II

I

Ans: I Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium 351. Rank the following alcohols in decreasing order of acidity. Explain your answer. F

F

OH

OH

OH F

F

III

II

I

Ans: I>III>II The negative charge on the conjugate base of compound I is stabilized by three electron withdrawing fluorine atoms via inductive effect, making it the weakest base and the alcohol strongest acid. The negative charge on the conjugate base of compound II is not stabilized, as it does not have any electronegative atoms on the carbon chain, making it a stronger base and the alcohol weakest acid. The negative charge on the conjugate base of compound III is less stabilized than I, because it has only one fluorine atom connected. Thus making it a stronger acid than II, but a weaker acid than I.

Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium 362. Rank the following alcohols in decreasing order of acidity. O2 N

OH

I

Ans: I>III>II Topic: Acidity of alcohols and phenols

OH

II

NC

OH

III

Section: 13.2 Difficulty Level: Medium 373. Predict the product(s) for the following reaction. OH

Na

ONa

Ans:

+

1 H2 2

Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium 38. Predict the product(s) for the following reaction. OH

Li

Ans:

O Li

+

1 H2 2

Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium 394. Predict the product for the following reaction. OH

1. NaH 2. CH3CH2Br

Ans:

Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium

O

3540. Provide the reagents necessary to carry out the following conversion. CH3CH2CH2CHCH3 CH3CH2CH2CH2CH2OH Br

Ans:

1. 2. 3. 4.

(CH3)3COK BH3 •THF H2O2/NaOH/H2O

Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium 4136. Predict the product(s) for the following reaction. 1. BH3 THF 2. H2O2/NaOH/H2O

CH2OH OH

OH

+ enantiomer I

A) B) C) D) E)

I II III IV None of these Ans: B

Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium

OH

+ enantiomer II

III

IV

4237. Predict the product for the following reaction.

1. Hg(OAc)2, H2O 2. NaBH4 CH2OH

OH

OH

II

I

A) B) C) D) E)

OH

III

IV

I II III IV None of these Ans: C

Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium 3843. Provide the reagents necessary to carry out the following conversion. (E)-3-methyl-3-hexene

3-methyl-3-hexanol

Ans: H3O+ OR 1. Hg(OAc)2, H2O 2. NaBH4 Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium 3944. Predict the major product for the following reaction. H3O+

Ans:

OH

Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium 450. Predict the product for the following reaction.

1. Hg(OAc)2, H2O 2. NaBD4

OH OH

I

A) B) C) D) E)

OH

OH

D

III

II

D

D

OH

IV

V

I II III IV V Ans: C

Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium 461. Provide the reagents necessary to carry out the following conversion. Br

Ans: NaOH Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Hard

OH

472. Provide the reagents necessary to carry out the following conversion. OH Cl

A) B) C) D) E)

NaOH/H2O 1. NaOCH3, 2. H3O+ 1. (CH3)3COK, 2. BH3, •THF, 3. H2O2/NaOH/H2O 1. (CH3)3COK, 2. H3O+ B&D Ans: D

Topic: Oxidation states Section: 13.4 Difficulty Level: Easy 483. What is the oxidation state of the carbon atoms I and II in the following reactioncompound? O

II

H

I

A) B) C) D) E)

I. +1, II. +2 I. +2, II. +2 I. +1, II. +3 I. +3, II. +2 I. +2, II. +1 Ans: E

Topic: Oxidation states Section: 13.4 Difficulty Level: Easy

O

494. What is the oxidation state of the carbon atoms I and II in the following reaction? O

CH3CH I

A) B) C) D) E)

O

CH3COH II

I. +1, II. +2 I. +2, II. +2 I. +1, II. +3 I. +3, II. +2 I. +2, II. +1 Ans: C

Topic: Oxidation states Section: 13.4 Difficulty Level: Medium 450. For the following conversion, identify if the starting material has been oxidized, reduced or neither. Explain your answer. OH

O

Ans: Oxidized. The carbon atom bonded to OH in the starting compound has a zero oxidation state and the carbonyl carbon atom in the product has an oxidation state of +2. Topic: Oxidation states Section: 13.4 Difficulty Level: Medium 5146. For the following conversion, identify if the starting material has been oxidized, reduced or neither. Cl

Cl

Ans: Oxidized. Topic: Oxidation states Section: 13.4

Difficulty Level: Medium 4752. For the following conversion, identify if the starting material has been oxidized, reduced or neither. Explain your answer. OH

O

Ans: Neither. The oxidation state of the carbon atoms is not changed. Topic: Oxidation states Section: 13.4 Difficulty Level: Hard 4853. For the following conversion, identify if the starting material has been oxidized, reduced or neither. O H

O

A) B) C) D)

reduced oxidized neither A& B Ans: B

Topic: Oxidation states Section: 13.4 Difficulty Level: Hard 54. For the following conversion, identify if the starting material has been oxidized, reduced or neither. OH

O

A) B) C) D)

reduced oxidized neither A& B Ans: C

Topic: Preparation of Alcohols via Reduction Section: 13.4

O

O

Difficulty Level: Easy 4955. Predict the product for the following reaction. O

CH3CCH2CH2CH3

NaBH4/CH3OH

OH

Ans:

CH3CHCH2CH2CH3 Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Medium 560. Predict the product for the following reaction. O

H

NaBH4/CH3OH

O

OH

A) B) C) D)

I II III IV Ans: A

I

OH

OH

OH

II

Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Medium

III

OH

IV

571. Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH4 followed by water? O

O O H

I

II

O

O

III

H

A) B) C) D) E)

I II III IV V Ans: A

IV

V

Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Hard 582. Provide the reagents necessary to carry out the following conversion. OH HC

CCH2CH2CH3

CH3CHCH2CH2CH3

+

Ans: 1. H3O / HgSO4 2. NaBH4/CH3OH OR 1. H2/Ni2B (OR Na, NH3) 2. H3O+ Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Hard

593. Predict the product for the following reaction. O

H

H2.Pd

O

OH

A) B) C) D)

I II III IV Ans: C

OH

II

I

Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Hard 5460. Predict the product for the following reaction. O COCH3

NaBH4 / H2O

O

O

Ans:

OH

OH

COCH3

H HO

Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Hard

III

OH

IV

5561. Predict the product for the following reaction. O COCH3

1. LiAlH4 excess 2. H2O O

CH2OH

Ans:

H HO

Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Hard 5662. Predict the product for the following reaction. H2O / H2SO4 HgSO4

Ans: OH

Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Medium

NaBH4/CH3OH

5763. Provide the reactant (A) for the following reaction 1. LiAlH4 5-methyl-3-heptanol A 2. H2O O

O O H

I

II O

O

III

H

IV

A) B) C) D) E)

V

I II III IV V Ans: A

Topic: Preparation of Diols Section: 13.5 Difficulty Level: Easy 5864. Provide the reagents necessary to carry out the following conversion. A) B) C) D) E)

cyclohexene KMnO4, NaOHcold KMnO4, H3O+, 75oC H2SO4, heat 1. mCPBA 2. H3O+ none of these Ans: A

Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium

cis-1,2-cyclohexanediol

5965. Predict the product(s) for the following reaction sequence. H2/Ni2B 1. OsO4 3-hexyne 2. NaHSO3 H

H

HO

A) B) C) D) E)

HO

OH

HO

I

HO

H

H

H

II

OH

H

III

I II III Both I & II None of these Ans: BA

Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium 660. Provide the reagents necessary to carry out the following conversion. A) B) C) D) E)

cyclohexene KMnO4, NaOH KMnO4, H3O+, 75oC H2SO4, heat 1. mCPBA 2. H3O+ none of these Ans: D

trans-1,2-cyclohexanediol

Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium 671. Provide the structure(s) of the each product (A-D)(s) in the following reaction sequence. CH3CH2ONa A B

Br2 h

mCPBA

Ans:

C

NaOH/H2O

D CH3

CH3 Br

OH

O

OH

A

B

C

+ enantiomer

+ enantiomer D

H

Topic: Preparation of Diols Section: 13.5 Difficulty Level: Hard 682. Predict the product for the following reaction. O

O

excess H

OH

NaBH4/CH3OH

OH

O

O

OH

OH

H

II

I OH

III OH

OH

OH

OH

IV

A) B) C) D) E)

I II III IV V Ans: C

Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium

V

693. Predict the product(s) for the following reaction. O

H3O+

OH

OH

H O

OH

A) B) C) D) E)

OH

OH

II

I

IV

III

I II III IV none of these Ans: C

Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium 7064. Provide the reagent(s) necessary to carry out the following conversion. OH

OH

Ans: 1. mCPBA 2. H3O+ OR NaOH/H2O Topic: Preparation of Diols Section: 13.5 Difficulty Level: Hard 6571. Provide the reagent(s) necessary to carry out the following conversion. OH OH

Ans:

1. 2. 3. 4.

O3 (CH3)2S excess NaBH4/CH3OH

Topic: Preparation of Diols Section: 13.5 Difficulty Level: Hard 6672. Predict the product(s) for the following reaction. O

O

1. excess LiAlH4 2. H2O

O

Ans:

OH OH

OH

Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Easy 6773. Predict the product for the following reaction sequence. O

1. CH3CH2MgBr 2. H2O

Ans:

HO

Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium

6874. Predict the product for the following reaction sequence. O

1.

Mg/ether

H

Br

2. H2O

Ans:

OH

Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium 6975. Provide the reagent(s) necessary to carry out the following conversion. O

O

Ans: 1. excess CH3MgBr/ether 2. H2O Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium

OH

760. Predict the product for the following reaction. O

1. CH3CH2CH2MgBr/ether 2. H2O

OH

OH

HO

OH

I

A) B) C) D) E)

III

II

I II III IV None of these Ans: A

Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium 771. Predict the product for the following reaction. O

Br

1.

Mg/ether

H

H

2. H2O

Ans:

OH

Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium

IV

78. Using Grignard reaction, show how you could prepare the following alcohol. OH

Ans:

MgBr

1.

O C H

H

2. H2O

Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium 79. Using Grignard reaction, show how you could prepare the following alcohol.

OH

Ans: 1. MgBr 2. H2O

O

OR 1.

MgBr

O

2. H2O

Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard

80. Using Grignard reaction, show how you could prepare the following alcohol.

HO

Ans: MgBr

1. O

2. H2O

OR 1.

O

MgBr

2. H2O

OR

1. O

MgBr

2. H2O

Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard 7281. Provide the reagent(s) necessary to carry out the following conversion. HO

Ans: 1. HBr 2. Mg/ether O

3. H 4. H2O

H

Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard

7382. Provide the reagent(s) necessary to prepare 1-isopropylcyclopentanol using a Grignard reaction. O

Ans:

MgBr

1. 2. H2O

Topic: Preparation of alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium 7483. Predict the product for the following reaction. O

OCH3

excess 1. CH3CH2CH2MgBr 2. H2O

Ans:

OH

Topic: Preparation of alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard 84. Predict the product for the following reaction. O

O

excess 1. CH3CH2MgBr 2. H2O

Ans: OH

OH

Topic: Preparation of alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard

85. Predict the product for the following reaction. excess 1. CH3CH2MgBr

O

O

2. H2O

O

Ans: OH

Topic: Preparation of alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard 86. Predict the product for the following reaction and provide a curved arrow mechanism for the formation of the product. excess 1. CH3CH2MgBr

O

O

2. H2O

O

Ans: OH

Mechanism O

O

O

CH3CH2MgBr O

O

O

CH3CH2MgBr

O

O

+ CH3OMgBr O

O

CH3CH2MgBr O

+ CH3OMgBr

O O

H

H HO

+ OH

Topic: Protection of alcohols Section: 13.7 Difficulty Level: Hard

7587. Provide the reagent(s) necessary to carry out the following conversion. OH HO

Br

HO

Ans: 1. (CH3)3SiCl / (CH3CH2)3N 2. Mg/ether O

3. 4. H2O 5. TBAF Topic: Protection of alcohols Section: 13.7 Difficulty Level: Hard 88. Provide the reagent(s) necessary to carry out the following conversion. OH

O

HO

HO

Ans: 1. CH3)3SiCl / (CH3CH2)3N 2. MgBr

3. H2O 4. TBAF Topic: Protection of alcohols Section: 13.7 Difficulty Level: Medium

7689. Predict the structure of each product(A-D)s) for the following reaction sequence. OH O

1. Br

(CH3)3SiCl

A

Mg/ ether

(CH3CH2)3N

B

2. H2O

C

Ans: OSi(CH3)3

OSi(CH3)3

MgBr

Br

A

B

OH

OSi(CH3)3

HO

HO

D

C

Topic: Protection of alcohols Section: 13.7 Difficulty Level: Medium 7790. Predict the product(s) for the following reaction sequence. 1.

OH

(CH3)3SiCl Br

A) B) C) D) E)

2,4-heptanediol 1,4-heptanediol 2,5-octanediol 1,5-octanediol none of these Ans: B

Topic: Protection of alcohols Section: 13.7 Difficulty Level: Medium

(CH3CH2)3N

Mg/ ether

H

O H

2. H2O

TBAF

TBAF

D

7891. Provide the reagents necessary to carry out the following conversion. HO

HO

Ans:

1. 2. 3. 4.

(CH3)3SiCl / (CH3CH2)3N NaNH2 CH3CH2CH2Br TBAF

Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Easy 7992. Which of the following could be used to synthesize 1-bromopentane? A) B) C) D) E)

CH3CH2CH2CH=CH2 + CH3CH2CH2CH2CH2OH CH3CH2CH2CH2CH2OH CH3CH2CH2CH2CH2OH CH3CH2CH2CH=CH2 + Ans: B

HBr  + PBr3  + NaBr  + Br2  Br2 

Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Easy 8093. Provide the reagents necessary to convert 3-methyl-2-butanol to 2-bromo-3methylbutane. A) conc. HBr B) Br2 C) NaBr, H2SO4 D) PBr3 E) HBr, peroxide Ans: D Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium

8194. Predict the product for the following reaction. OH

PBr3

Br

Ans:

Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Hard 8295. Predict the major product for the following reaction and provide a curved arrow mechanism for the formation of the product. OH

HBr

Ans: Br

Mechanism OH

H

Br

OH2

+ Br H

Br Br

Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Hard

+ H2O

8396. Predict the major product for the following reaction.

OH

HCl

Ans: Cl

Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 8497. Predict the product for the following reaction. SOCl2/pyridine OH

Ans:

Cl

Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium

8598. Predict the major product for the following reaction. H OH

CH3 H

1. TsCl /pyridine 2. NaI

H

H I

CH3

I

A) B) C) D) E)

H

II

H

I

H

OTs

H

Ts

CH3

CH3

CH3

III

H

IV

H

I II III IV both I and III Ans: C

Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 8699. Predict the product when cis-3-methylcyclopentanol is treated with TsCl/pyridine, followed by sodium bromide. A) trans-1-bromo-3-methylcyclopentane B) cis-1-bromo-3-methylcyclopentane C) 1-methylcyclopentene D) 2-mMethylcyclopentene E) 3-mMethylcyclopentene Ans: A Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 87100 The reaction between 2-methyl-2-pentanol and sulfuric acid to yield 2-methyl-2-pentene . goes via a(n) _____. A) B) C) D) E)

SN1 mechanism SN2 mechanism E1 mechanism E2 mechanism None of these. Ans: C

Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 88101 Explain why the following reaction will not produce an alcohol as product. . Cl

OH

NaOH not produced

Ans: The tertiary halide is too sterically hindered for an SN2 reaction with hydroxide as nucleophile. Instead, the hydroxide ion is a strong base and will react with the alkyl chloride to form alkene via an E2 mechanism. Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 89102 Predict the major product for the following reaction. . OH

1. TsCl/pyridine 2. CH3CH2ONa

Ans:

Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium

90103 Predict the major product for the following reaction. OH . H2SO4 

Ans:

Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 91104 Provide the reagent(s) necessary to convert cyclohexanol to cyclohexane. . . Ans: 1. H2SO4, heat 2. H2/Pd OR OR 1. TsCl/pyridine 2. CH3CH2ONa 3. H2/Pd 4.

Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium

92105 Provide a stepwise curved arrow mechanism for the following reaction. HO . CH2CH3 CH2CH3

CH2CH3 CH2CH3

H2SO4  O

Ans: HO

CH2CH3 CH2CH3

H

O

S

O

H2O

H

CH2CH3 O CH2CH3

O

O

+

S

O

H

O

H

O H3CH2C

H3CH2C CH2CH3

H

O

CH2CH3

O

CH2CH3

CH2CH3

+ H2O CH2CH3

+ H2SO4 CH2CH3

Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Hard

S O

93106 Predict the product and provide a stepwise curved arrow mechanism for the following . reaction. OH OH

H2SO4 heat

Ans: O

Mechanism O OH

H

O

S

O

H OH2

OH

O

O OH

+

O

S

O

H

O O H

O OH

+ H2O

Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Easy

H

O

S

O O

H

O

+ H2SO4

94107 Predict the product for the following reaction. PCC . 2-hexanol CH2Cl2 O A) CH3COH O

B)

CH3CH2CH2CH2COH O

C)

CH3(CH2)3CCH3

D)

O

CH3CH2CH2CH2CH2COH O

E)

CH3CH2CH2CH2CH2CH

Ans: C Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium 95108 Provide the reagents necessary to carry out the following conversion. O OH .

A) B) C) D) E)

KMnO4/NaOH/H2O Na2Cr2CrOO73/H2SO4/H2O H2, Pt Br2, CCl4 None of these Ans: B

Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Easy

96109 Predict the product for the following reaction. OH . Na2Cr2O7/H2SO4/H2O

Ans:

O

Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Easy 97110 Predict the product for the following reaction. OH . PCC CH2Cl2 H

Ans: O

Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Easy 98111 Provide the reagents necessary to carry out the following conversion. . O

OH

A) B) C) D) E)

KMnO4/NaOH/H2O Na2Cr2O7CrO3/H2SO4/H2O PCC/CH2Cl2 Br2, CCl4 None of these Ans: C

Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium

H

99112 Provide the reagents necessary to carry out the following conversion. . O

OH

A) B) C) D) E)

OH

KMnO4/NaOH/H2O Na2Cr2O7CrO3/H2SO4/H2O PCC/CH2Cl2 Br2, CCl4 None of these Ans: B

Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium 11300 Predict the product for the following reaction. . OH

excess PCC/CH2Cl2

Ans:

CH2OH OH

CH O

Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium 11401 Predict the product for the following reaction. .

OH

PCC CH2Cl2

Ans: No reaction. Tertiary alcohols do not undergo oxidation reactions.

Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium 11502 Predict the product for the following reaction. PCC . cis-4-methylcyclohexanol

CH2Cl2

Ans:

O

. Topic: Oxidation of Phenols Section: 13.12 Difficulty Level: Medium 116. Predict the product for the following reaction. OH

Na2Cr2O7/H2SO4/H2O

Ans:

O

O

.

Topic: Synthesis Section: 13.13 Difficulty Level: Medium

11703 Provide the structure for the final product (D), in the following reaction sequence. O . CH3CH2CHOH

PBr3

A

Mg ether

H3C

H

B

C

H2O

D

CH3 OH

Ans:

Topic: Synthesis Section: 13.13 Difficulty Level: Medium 118. Provide the structure for each product (A-C) in the following reaction sequence. 1. O CH3CH2CHOH

PBr3

A

Mg ether

CH3

B

H3C

H

C 2. H2O OH

Ans: Br

A

Topic: Synthesis Section: 13.13 Difficulty Level: Hard

MgBr

B

C

11904 Provide the structure for the final product (E), in the following reaction sequence. O . PBr3

OH

Mg

A

B

ether

H

H

H2O

C

D

PCC

OH

O H

OH

II

I

A) B) C) D) E)

E

CH2Cl2

III

V

IV O

O

I II III IV V Ans: C

Topic: Synthesis Section: 13.13 Difficulty Level: Hard 120. Provide the structure for each product (A-D) in the following reaction sequence. 1. PBr3

OH

Mg

A

ether

B

O

H

H

2. H2O

PCC

C

D

CH2Cl2

Ans:

A

Topic: Synthesis Section: 13.13 Difficulty Level: Medium

O

OH

Br

MgBr

B

C

D

10512 Provide the structure for product (A), in the following reaction sequence. 1. OH

PBr3

Mg

D2O

A

ether

A) B) C) D) E)

CH3CH2CH2CH3 CH3CH2CHDCH3 CH3CH2CHODCH3 CH3CH2CH2CH2OD CH3CH2CH2CH2D Ans: B

Topic: Synthesis Section: 13.13 Difficulty Level: Medium 10612 Provide the reagents necessary to carry out the following conversion. O 2. OH

Ans:

1. 2.

PBr3 Mg/ether O H

3. 4. 5.

H2O PCC/CH2Cl2

Topic: Synthesis Section: 13.13 Difficulty Level: Hard

10712 Provide a stepwise synthesis for the following. 3.

Cl

Ans: Cl2

OH

CH3CH2ONa

H3O+

PCC

h

CH2Cl2

O

OH

H2SO4

1. CH3MgBr 2. H2O

heat

Topic: Synthesis Section: 13.13 Difficulty Level: Hard 10812 Provide the product for the following reaction sequence: MgBr 4. OH

PCC CH2Cl2

I

O

IV

A) B) C) D) E)

I II III IV V Ans: C

H2O

K2Cr2O7/H2SO4/H2O

H2O

ether

ether

O

OH

MgBr

HO

III

II

V

Topic: Synthesis Section: 13.13 Difficulty Level: MediumHard 10912 Predict the product, for the following reaction sequence, O 5. 3,4-dimethyl-1-hexanol

SOCl2

Mg/ether

pyridine

1.

H

CrO3/ H2SO4/H2O

2. H3O+ O

OH

III

II

I

OH

IV

A) B) C) D) E)

6,7-dimethyl-3-nonanolI 6,7-dimethyl-3-nonanoneII 6,7-dimethyl-3-nonanalIII 3,4-dimethyl-7-nonanolIV 3,4-dimethyl-7-nonanoneV Ans: B

Topic: Synthesis Section: 13.13 Difficulty Level: Hard

O

OH

H

V

O

11012 Provide a stepwise synthesis for the following. 6. O

Ans:

Cl OH

CH3CH2ONa

Br2 h

1. BH3 THF

PCC

2. H2O2/NaOH/H2O

CH2Cl2

O

Topic: Synthesis Section: 13.13 Difficulty Level: Hard 11112 Provide the reagents necessary to carry out the following conversion. O 7. O

Ans:

1. 2. 3. 4.

Cl2/h CCONa KMnO4/NaOH/H2O excess PCC/CH2Cl2

5.

Topic: Synthesis Section: 13.13 Difficulty Level: Hard

11212 Provide the reagents necessary to carry out the following conversion. O HO 8. HO

HO

Ans:

1. 2. 3.

(CH3)3SiCl/ (CH3CH2)3N CH3MgBr H3O+

4.

Topic: Synthesis Section: 13.13 Difficulty Level: Medium 11312 Provide the reagents necessary to carry out the following conversion. O 9. Br

Ans: 1. NaOH 2. Na2Cr2O7/H2SO4/H2O 3. Topic: Synthesis Section: 13.13 Difficulty Level: Hard

OH

11413 Provide a stepwise synthesis to carry out the following conversion. 0.

Ans: Br

Br2

1. BH3 THF

CH3CH2ONa

h

OH

2. H2O2/NaOH/H2O

PCC O

CH2Cl2

CH3

1. CH3MgBr 2. H2O

H2SO4

OH

heat

H2/Pd

Br

Br2

CH3CH2ONa

h

2. H2O2/NaOH/H2O

PCC CH2Cl2

H2/Pd

Topic: Synthesis Section: 13.13 Difficulty Level: Hard

1. BH3

O

1. CH3MgBr 2. H2O

CH3 OH

H2SO4 heat

OH

131. Provide a stepwise synthesis to carry out the following conversion. O OH OH

Ans: OH

PBr3

Br

Mg/ether

MgBr

O

1. O H

H

OH

2. H2O

CrO3/H2SO4/H2O

OH

Topic: Spectroscopy Section: 13 & 15.6 Difficulty Level: Medium 132. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

OH

I

A) B) C) D) E)

I II III IV V Ans: A

Topic: Spectroscopy Section: 13 & 15.6 Difficulty Level: Medium

OH

II

OH C N

III

O HO

C

IV

N

133. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

OH OH

I

A) B) C) D) E)

I II III IV V Ans: E

Topic: Spectroscopy Section: 13, 16.11 & 16.12 Difficulty Level: Hard

II

OH

O

O

OH

III

IV

OH

V

134. Which of the following compounds is consistent with the following proton decoupled 13 C NMR spectrum?

80

70

60

50

40 PPM OH

OH

30

20

OH

HO

I

A) B) C) D) E)

I II III IV none of these Ans: B

Topic: Spectroscopy Section: 13, 16.11 & 16.12 Difficulty Level: Hard

II

III

IV

10

0

135. Which of the following compounds is consistent with the following proton decoupled 13 C NMR spectrum?

70

60

50

40 PPM

30

20

10

OH

OH HO

I

A) B) C) D) E)

I II III IV none of these Ans: A

Topic: Spectroscopy Section: 13, 16.11 & 16.12 Difficulty Level: Hard

II

III

IV OH

0

136. A compound with a molecular formula C9H12O has the following 1HNMR spectrum. Which of the following structures is consistent with this spectrum?

3 2

2

2

2

1 exchanges with D2O

7

6

O

I

A) B) C) D) E)

I II III IV V Ans: C

Topic: Spectroscopy Section: 13, 16.11 & 16.12 Difficulty Level: Hard

5

4 PPM

3

1

OH

OH

II

2

III OH

IV

0 OH

V

137. A compound with a molecular formula C6H14O displays the following 1HNMR and 13 CNMR spectra. Propose astructure for this compound.

9

3 2

90

80

70

Ans:

OH

60

50

PPM

40

1

30

20

10

0

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