(a) Interpretation: The synthesis of in enantiomerically pure form from enantiomerically pure is to be stated. Concept introduction: When an allylic alcohol is reacted with enantiomeric tartrate esters, and ( − ) DET , in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET , used. The epoxide formed undergoes stereospecific ring opening reactions.

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Answer 1

Question

Chapter 11, Problem 11.62AP

Interpretation Introduction

(a)

Interpretation:

The synthesis of in enantiomerically pure form from enantiomerically pure is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Interpretation Introduction

(b)

Interpretation:

The synthesis of (2R, 3S)-3-methoxybutan-2-one in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Interpretation Introduction

(c)

Interpretation:

The synthesis of (2R, 3S)-2-ethoxy-3-methoxybutane in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Interpretation Introduction

(d)

Interpretation:

The synthesis of (2S, 3R)-2-ethoxy-3-methoxybutane in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

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6. Consider the following exothermic reaction below. 2Cu2+(aq) +41 (aq)2Cul(s) + 12(aq) a. If Cul is added, there will be a shift left/shift right/no shift (circle one). b. If Cu2+ is added, there will be a shift left/shift right/no shift (circle one). c. If a solution of AgNO3 is added, there will be a shift left/shift right/no shift (circle one). d. If the solvent hexane (C6H14) is added, there will be a shift left/shift right/no shift (circle one). Hint: one of the reaction species is more soluble in hexane than in water. e. If the reaction is cooled, there will be a shift left/shift right/no shift (circle one). f. Which of the changes above will change the equilibrium constant, K?

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Answer 2

Question

Chapter 11, Problem 11.62AP

Interpretation Introduction

(a)

Interpretation:

The synthesis of in enantiomerically pure form from enantiomerically pure is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Interpretation Introduction

(b)

Interpretation:

The synthesis of (2R, 3S)-3-methoxybutan-2-one in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Interpretation Introduction

(c)

Interpretation:

The synthesis of (2R, 3S)-2-ethoxy-3-methoxybutane in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Interpretation Introduction

(d)

Interpretation:

The synthesis of (2S, 3R)-2-ethoxy-3-methoxybutane in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

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Answer 3

Question

Chapter 11, Problem 11.62AP

Interpretation Introduction

(a)

Interpretation:

The synthesis of in enantiomerically pure form from enantiomerically pure is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Interpretation Introduction

(b)

Interpretation:

The synthesis of (2R, 3S)-3-methoxybutan-2-one in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Interpretation Introduction

(c)

Interpretation:

The synthesis of (2R, 3S)-2-ethoxy-3-methoxybutane in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Interpretation Introduction

(d)

Interpretation:

The synthesis of (2S, 3R)-2-ethoxy-3-methoxybutane in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

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Answer 4

Question

Chapter 11, Problem 11.62AP

Interpretation Introduction

(a)

Interpretation:

The synthesis of in enantiomerically pure form from enantiomerically pure is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Interpretation Introduction

(b)

Interpretation:

The synthesis of (2R, 3S)-3-methoxybutan-2-one in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Interpretation Introduction

(c)

Interpretation:

The synthesis of (2R, 3S)-2-ethoxy-3-methoxybutane in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Interpretation Introduction

(d)

Interpretation:

The synthesis of (2S, 3R)-2-ethoxy-3-methoxybutane in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

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Answer 5

Chapter 11, Problem 11.62AP

Interpretation Introduction

(a)

Interpretation:

The synthesis of in enantiomerically pure form from enantiomerically pure is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Interpretation Introduction

(b)

Interpretation:

The synthesis of (2R, 3S)-3-methoxybutan-2-one in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Interpretation Introduction

(c)

Interpretation:

The synthesis of (2R, 3S)-2-ethoxy-3-methoxybutane in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Interpretation Introduction

(d)

Interpretation:

The synthesis of (2S, 3R)-2-ethoxy-3-methoxybutane in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Answer 6

Chapter 11, Problem 11.62AP

Interpretation Introduction

(a)

Interpretation:

The synthesis of in enantiomerically pure form from enantiomerically pure is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Answer 7

Chapter 11, Problem 11.62AP

Interpretation Introduction

(a)

Interpretation:

The synthesis of in enantiomerically pure form from enantiomerically pure is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The synthesis of (2R, 3S)-3-methoxybutan-2-one in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The synthesis of (2R, 3S)-3-methoxybutan-2-one in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The synthesis of (2R, 3S)-2-ethoxy-3-methoxybutane in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The synthesis of (2R, 3S)-2-ethoxy-3-methoxybutane in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Answer 12

Interpretation Introduction

(d)

Interpretation:

The synthesis of (2S, 3R)-2-ethoxy-3-methoxybutane in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Answer 13

Interpretation Introduction

(d)

Interpretation:

The synthesis of (2S, 3R)-2-ethoxy-3-methoxybutane in enantiomerically pure form from enantiomerically pure (2R, 3R)-2, 3-dimethyloxirane is to be stated.

Concept introduction:

When an allylic alcohol is reacted with enantiomeric tartrate esters, (+)DET and (−)DET, in presence of titanium (IV) isopropoxide catalyst and tert-butylhydroperoxide, two enantiomeric epoxides are formed. This reaction is known as Sharpless asymmetric epoxidation reaction. The epoxide is formed at the double bond present in the allylic alcohol. The stereochemistry of the enantiomeric epoxide products depends upon the stereochemistry of the tartrate ester, DET, used. The epoxide formed undergoes stereospecific ring opening reactions.

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 11 - Prob. 11.1P Ch. 11 - Prob. 11.2P Ch. 11 - Prob. 11.3P Ch. 11 - Prob. 11.4P Ch. 11 - Prob. 11.5P Ch. 11 - Prob. 11.6P Ch. 11 - Prob. 11.7P Ch. 11 - Prob. 11.8P Ch. 11 - Prob. 11.9P Ch. 11 - Prob. 11.10P

Solution Summary: The author explains that enantiomeric epoxides are formed at the double bond present in the allylic alcohol and undergo stereospecific ring opening reactions.

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Chapter 11 Solutions