(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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I have a question about this problem involving mechanisms and drawing curved arrows for acids and bases. I know we need to identify the nucleophile and electrophile, but are there different types of reactions? For instance, what about Grignard reagents and other types that I might not be familiar with? Can you help me with this? I want to identify the names of the mechanisms for problems 1-14, such as Gilman reagents and others. Are they all the same? Also, could you rewrite it so I can better understand? The handwriting is pretty cluttered. Additionally, I need to label the nucleophile and electrophile, but my main concern is whether those reactions differ, like the "Brønsted-Lowry acid-base mechanism, Lewis acid-base mechanism, acid-catalyzed mechanisms, acid-catalyzed reactions, base-catalyzed reactions, nucleophilic substitution mechanisms (SN1 and SN2), elimination reactions (E1 and E2), organometallic mechanisms, and so forth."

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