(a) Interpretation: The major product of the reaction is to be predicted. Concept introduction: Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyllithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R - nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Question

11 1 Which one of the following compounds would show a proton NMR signal at the highest chemical shift? (7pts) cl @amitabh CI CI d) Cl CICI

Answer 1

Question

Chapter 17, Problem 17.29P

Interpretation Introduction

(a)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyllithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(c)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

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11 1 Which one of the following compounds would show a proton NMR signal at the highest chemical shift? (7pts) cl @amitabh CI CI d) Cl CICI

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H2SO4 (cat.), H₂O 100 °C NH₂

Answer 2

Question

Chapter 17, Problem 17.29P

Interpretation Introduction

(a)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyllithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(c)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

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Answer 3

Question

Chapter 17, Problem 17.29P

Interpretation Introduction

(a)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyllithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(c)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

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Answer 4

Question

Chapter 17, Problem 17.29P

Interpretation Introduction

(a)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyllithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(c)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

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Answer 5

Chapter 17, Problem 17.29P

Interpretation Introduction

(a)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyllithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(c)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Answer 6

Chapter 17, Problem 17.29P

Interpretation Introduction

(a)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyllithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Answer 7

Chapter 17, Problem 17.29P

Interpretation Introduction

(a)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyllithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Answer 12

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Answer 23

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 Grignard reagents and alkyl lithium undergo direct addition to,-unsaturated carbonyls.

Chapter 17 Solutions