(a) Interpretation: The major product of the given reaction is to be predicted. Concept introduction: Lithium dialkylcuprates, R 2 CuLi , are the most common organocuprates. They are also referred to as Gillman reagents. Lithium dialkylcuprate is a source of nucleophile R - , which adds to the β- carbon of α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH 4 + from NH 4 Cl . Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

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Answer 1

Question

Chapter 17, Problem 17.28P

Interpretation Introduction

(a)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuprates. They are also referred to as Gillman reagents. Lithium dialkylcuprate is a source of nucleophile R-, which adds to the β- carbon of α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuprates. They are also referred to as Gillman reagents. Lithium dialkylcuperate is a source of the nucleophile R-, which adds to the β- carbon of a α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

Interpretation Introduction

(c)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuperates. They are also referred to as Gillman reagents. This Lithium dialkylcuperate is a source of the nucleophile R-, which adds to the β- carbon of an α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

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Answer 2

Question

Chapter 17, Problem 17.28P

Interpretation Introduction

(a)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuprates. They are also referred to as Gillman reagents. Lithium dialkylcuprate is a source of nucleophile R-, which adds to the β- carbon of α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuprates. They are also referred to as Gillman reagents. Lithium dialkylcuperate is a source of the nucleophile R-, which adds to the β- carbon of a α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

Interpretation Introduction

(c)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuperates. They are also referred to as Gillman reagents. This Lithium dialkylcuperate is a source of the nucleophile R-, which adds to the β- carbon of an α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

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Answer 3

Question

Chapter 17, Problem 17.28P

Interpretation Introduction

(a)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuprates. They are also referred to as Gillman reagents. Lithium dialkylcuprate is a source of nucleophile R-, which adds to the β- carbon of α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuprates. They are also referred to as Gillman reagents. Lithium dialkylcuperate is a source of the nucleophile R-, which adds to the β- carbon of a α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

Interpretation Introduction

(c)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuperates. They are also referred to as Gillman reagents. This Lithium dialkylcuperate is a source of the nucleophile R-, which adds to the β- carbon of an α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

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Answer 4

Question

Chapter 17, Problem 17.28P

Interpretation Introduction

(a)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuprates. They are also referred to as Gillman reagents. Lithium dialkylcuprate is a source of nucleophile R-, which adds to the β- carbon of α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuprates. They are also referred to as Gillman reagents. Lithium dialkylcuperate is a source of the nucleophile R-, which adds to the β- carbon of a α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

Interpretation Introduction

(c)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuperates. They are also referred to as Gillman reagents. This Lithium dialkylcuperate is a source of the nucleophile R-, which adds to the β- carbon of an α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

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Answer 5

Chapter 17, Problem 17.28P

Interpretation Introduction

(a)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuprates. They are also referred to as Gillman reagents. Lithium dialkylcuprate is a source of nucleophile R-, which adds to the β- carbon of α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuprates. They are also referred to as Gillman reagents. Lithium dialkylcuperate is a source of the nucleophile R-, which adds to the β- carbon of a α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

Interpretation Introduction

(c)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuperates. They are also referred to as Gillman reagents. This Lithium dialkylcuperate is a source of the nucleophile R-, which adds to the β- carbon of an α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

Answer 6

Chapter 17, Problem 17.28P

Interpretation Introduction

(a)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuprates. They are also referred to as Gillman reagents. Lithium dialkylcuprate is a source of nucleophile R-, which adds to the β- carbon of α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

Answer 7

Chapter 17, Problem 17.28P

Interpretation Introduction

(a)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuprates. They are also referred to as Gillman reagents. Lithium dialkylcuprate is a source of nucleophile R-, which adds to the β- carbon of α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuprates. They are also referred to as Gillman reagents. Lithium dialkylcuperate is a source of the nucleophile R-, which adds to the β- carbon of a α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuprates. They are also referred to as Gillman reagents. Lithium dialkylcuperate is a source of the nucleophile R-, which adds to the β- carbon of a α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuperates. They are also referred to as Gillman reagents. This Lithium dialkylcuperate is a source of the nucleophile R-, which adds to the β- carbon of an α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

Lithium dialkylcuprates, R2CuLi, are the most common organocuperates. They are also referred to as Gillman reagents. This Lithium dialkylcuperate is a source of the nucleophile R-, which adds to the β- carbon of an α,β- unsaturated carbonyl via conjugate addition. The resulting enolate anion is then protonated by NH4+ from NH4Cl. Lithium dialkylcuprates do not tend to undergo direct addition to a polar π bond.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 17 - Prob. 17.1P Ch. 17 - Prob. 17.2P Ch. 17 - Prob. 17.3P Ch. 17 - Prob. 17.4P Ch. 17 - Prob. 17.5P Ch. 17 - Prob. 17.6P Ch. 17 - Prob. 17.7P Ch. 17 - Prob. 17.8P Ch. 17 - Prob. 17.9P Ch. 17 - Prob. 17.10P

Solution Summary: The author explains that Lithium dialkylcuprates, a source of nucleophile, attack the - carbon of the unsaturated carbonyl.

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Chapter 17 Solutions