(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

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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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11:43 Q1. (a) (c) (d) (b) Two stereoisomers of but-2-ene are formed when 2-bromobutane reacts with ethanolic potassium hydroxide. (i) Explain what is meant by the term stereoisomers. Library Name and outline a mechanism for the reaction of 2-bromo-2-methylpropane with ethanolic potassium hydroxide to form the alkene 2-methylpropene, (CH3)2C=CH₂ Name of mechanism Mechanism (ii) Draw the structures and give the names of the two stereoisomers of but-2-ene. Stereoisomer 1 Name (iii) Name this type of stereoisomerism. Select Name Stereoisomer 2 When 2-bromo-2-methylpropane reacts with aqueous potassium hydroxide, 2-methylpropan-2-ol is formed as shown by the following equation. CH3 H₂C-C-CH3 + KOH Br Page 2 of 14 CH3 H3C-C-CH3 + KBr ОН State the role of the hydroxide ions in this reaction. Write an equation for the reaction that occurs when CH3CH₂CH₂CH₂Br reacts with an excess of ammonia. Name the organic product of this reaction. Equation Name of product 9,284 Photos, 1,166 Videos For You…

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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 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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