(a) Interpretation: The reason as to why the catalytic hydrogenation reaction of ( − ) -3-methyl-1-pentene results in the optically inactive product is to be stated. Concept introduction: A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called asymmetric or stereogenic centers. The chiral atom sometimes results in the formation of enantiomers which are the non-superimposable mirror images of each other.

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Answer 1

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Chapter 6, Problem 6.47AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why the catalytic hydrogenation reaction of (−)-3-methyl-1-pentene results in the optically inactive product is to be stated.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called asymmetric or stereogenic centers. The chiral atom sometimes results in the formation of enantiomers which are the non-superimposable mirror images of each other.

Interpretation Introduction

(b)

Interpretation:

The absolute configuration of (+)-3-methylhexane is to be stated when catalytic hydrogenation of (S)-(+)-3-methyl-1-hexene gives (−)-3-methylhexane.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers. The chiral atom sometimes results in the formation of enantiomers which are the non-superimposable mirror images of each other.

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A difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired conguration.a. Label this stereogenic center as R or S.b. A well known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship.c. Suggest a reagent to convert A to the single stereoisomer X.

A difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired configuration. a. Label this stereogenic center as R or S. b. A well-known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship. d. Suggest a reagent to convert A to the single stereoisomer X.

1-Chloro-1,2-diphenylethane can undergo E2 elimination to give either cis- or trans-1,2-diphenylethylene (stilbene). Draw Newman projections of the reactive conformations leading to both possible products, and suggest a reason why the trans alkene is the major product.

Answer 2

Question

Chapter 6, Problem 6.47AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why the catalytic hydrogenation reaction of (−)-3-methyl-1-pentene results in the optically inactive product is to be stated.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called asymmetric or stereogenic centers. The chiral atom sometimes results in the formation of enantiomers which are the non-superimposable mirror images of each other.

Interpretation Introduction

(b)

Interpretation:

The absolute configuration of (+)-3-methylhexane is to be stated when catalytic hydrogenation of (S)-(+)-3-methyl-1-hexene gives (−)-3-methylhexane.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers. The chiral atom sometimes results in the formation of enantiomers which are the non-superimposable mirror images of each other.

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Answer 3

Question

Chapter 6, Problem 6.47AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why the catalytic hydrogenation reaction of (−)-3-methyl-1-pentene results in the optically inactive product is to be stated.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called asymmetric or stereogenic centers. The chiral atom sometimes results in the formation of enantiomers which are the non-superimposable mirror images of each other.

Interpretation Introduction

(b)

Interpretation:

The absolute configuration of (+)-3-methylhexane is to be stated when catalytic hydrogenation of (S)-(+)-3-methyl-1-hexene gives (−)-3-methylhexane.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers. The chiral atom sometimes results in the formation of enantiomers which are the non-superimposable mirror images of each other.

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Answer 4

Question

Chapter 6, Problem 6.47AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why the catalytic hydrogenation reaction of (−)-3-methyl-1-pentene results in the optically inactive product is to be stated.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called asymmetric or stereogenic centers. The chiral atom sometimes results in the formation of enantiomers which are the non-superimposable mirror images of each other.

Interpretation Introduction

(b)

Interpretation:

The absolute configuration of (+)-3-methylhexane is to be stated when catalytic hydrogenation of (S)-(+)-3-methyl-1-hexene gives (−)-3-methylhexane.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers. The chiral atom sometimes results in the formation of enantiomers which are the non-superimposable mirror images of each other.

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Answer 5

Chapter 6, Problem 6.47AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why the catalytic hydrogenation reaction of (−)-3-methyl-1-pentene results in the optically inactive product is to be stated.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called asymmetric or stereogenic centers. The chiral atom sometimes results in the formation of enantiomers which are the non-superimposable mirror images of each other.

Interpretation Introduction

(b)

Interpretation:

The absolute configuration of (+)-3-methylhexane is to be stated when catalytic hydrogenation of (S)-(+)-3-methyl-1-hexene gives (−)-3-methylhexane.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers. The chiral atom sometimes results in the formation of enantiomers which are the non-superimposable mirror images of each other.

Answer 6

Chapter 6, Problem 6.47AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why the catalytic hydrogenation reaction of (−)-3-methyl-1-pentene results in the optically inactive product is to be stated.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called asymmetric or stereogenic centers. The chiral atom sometimes results in the formation of enantiomers which are the non-superimposable mirror images of each other.

Answer 7

Chapter 6, Problem 6.47AP

Interpretation Introduction

(a)

Interpretation:

The reason as to why the catalytic hydrogenation reaction of (−)-3-methyl-1-pentene results in the optically inactive product is to be stated.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called asymmetric or stereogenic centers. The chiral atom sometimes results in the formation of enantiomers which are the non-superimposable mirror images of each other.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The absolute configuration of (+)-3-methylhexane is to be stated when catalytic hydrogenation of (S)-(+)-3-methyl-1-hexene gives (−)-3-methylhexane.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers. The chiral atom sometimes results in the formation of enantiomers which are the non-superimposable mirror images of each other.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The absolute configuration of (+)-3-methylhexane is to be stated when catalytic hydrogenation of (S)-(+)-3-methyl-1-hexene gives (−)-3-methylhexane.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers. The chiral atom sometimes results in the formation of enantiomers which are the non-superimposable mirror images of each other.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 6 - Prob. 6.1P Ch. 6 - Prob. 6.2P Ch. 6 - Prob. 6.3P Ch. 6 - Prob. 6.4P Ch. 6 - Prob. 6.5P Ch. 6 - Prob. 6.6P Ch. 6 - Prob. 6.7P Ch. 6 - Prob. 6.8P Ch. 6 - Prob. 6.9P Ch. 6 - Prob. 6.10P

Solution Summary: The author explains the catalytic hydrogenation reaction of (-)-3-methyl-1-pentene produces an optically inactive product.

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