(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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Part VII. Below are the 'HNMR, 13 C-NMR, COSY 2D- NMR, and HSQC 2D-NMR (similar with HETCOR but axes are reversed) spectra of an organic compound with molecular formula C6H1003 - Assign chemical shift values to the H and c atoms of the compound. Find the structure. Show complete solutions. Predicted 1H NMR Spectrum 4.7 4.6 4.5 4.4 4.3 4.2 4.1 4.0 3.9 3.8 3.7 3.6 3.5 3.4 3.3 3.2 3.1 3.0 2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 f1 (ppm) Predicted 13C NMR Spectrum 100 f1 (ppm) 30 220 210 200 190 180 170 160 150 140 130 120 110 90 80 70 -26 60 50 40 46 30 20 115 10 1.0 0.9 0.8 0 -10

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