(a) Interpretation: The product obtained when 3-phenylprop-2-en-1-ol reacts with ( − ) -DET in presence of t e r t − butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

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Answer 1

Question

Chapter 11, Problem 11.41P

Interpretation Introduction

(a)

Interpretation:

The product obtained when 3-phenylprop-2-en-1-ol reacts with (−)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

Interpretation Introduction

(b)

Interpretation:

The product obtained when 2-methylbut-2-en-1-ol reacts with (+)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

Interpretation Introduction

(c)

Interpretation:

The product obtained when undec-2, 5, 9-trien-1-ol reacts with (−)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

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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."

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Answer 2

Question

Chapter 11, Problem 11.41P

Interpretation Introduction

(a)

Interpretation:

The product obtained when 3-phenylprop-2-en-1-ol reacts with (−)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

Interpretation Introduction

(b)

Interpretation:

The product obtained when 2-methylbut-2-en-1-ol reacts with (+)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

Interpretation Introduction

(c)

Interpretation:

The product obtained when undec-2, 5, 9-trien-1-ol reacts with (−)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

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Answer 3

Question

Chapter 11, Problem 11.41P

Interpretation Introduction

(a)

Interpretation:

The product obtained when 3-phenylprop-2-en-1-ol reacts with (−)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

Interpretation Introduction

(b)

Interpretation:

The product obtained when 2-methylbut-2-en-1-ol reacts with (+)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

Interpretation Introduction

(c)

Interpretation:

The product obtained when undec-2, 5, 9-trien-1-ol reacts with (−)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

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Answer 4

Question

Chapter 11, Problem 11.41P

Interpretation Introduction

(a)

Interpretation:

The product obtained when 3-phenylprop-2-en-1-ol reacts with (−)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

Interpretation Introduction

(b)

Interpretation:

The product obtained when 2-methylbut-2-en-1-ol reacts with (+)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

Interpretation Introduction

(c)

Interpretation:

The product obtained when undec-2, 5, 9-trien-1-ol reacts with (−)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

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Answer 5

Chapter 11, Problem 11.41P

Interpretation Introduction

(a)

Interpretation:

The product obtained when 3-phenylprop-2-en-1-ol reacts with (−)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

Interpretation Introduction

(b)

Interpretation:

The product obtained when 2-methylbut-2-en-1-ol reacts with (+)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

Interpretation Introduction

(c)

Interpretation:

The product obtained when undec-2, 5, 9-trien-1-ol reacts with (−)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

Answer 6

Chapter 11, Problem 11.41P

Interpretation Introduction

(a)

Interpretation:

The product obtained when 3-phenylprop-2-en-1-ol reacts with (−)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

Answer 7

Chapter 11, Problem 11.41P

Interpretation Introduction

(a)

Interpretation:

The product obtained when 3-phenylprop-2-en-1-ol reacts with (−)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The product obtained when 2-methylbut-2-en-1-ol reacts with (+)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The product obtained when 2-methylbut-2-en-1-ol reacts with (+)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The product obtained when undec-2, 5, 9-trien-1-ol reacts with (−)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The product obtained when undec-2, 5, 9-trien-1-ol reacts with (−)-DET in presence of tert− butyl hydroperoxide is to be stated. Also, the stereochemistry of the product 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 reation. 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.

Answer 12

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Answer 13

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Answer 14

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Answer 15

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 the enantiomer product is obtained when 3-phenylprop-2-en-1-ol reacts with (-) -DET

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Chapter 11 Solutions