Organic Chemistry: Principles And Mechanisms (second Edition)
Organic Chemistry: Principles And Mechanisms (second Edition)
2nd Edition
ISBN: 9780393630749
Author: KARTY, Joel
Publisher: W. W. Norton & Company
Question
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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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Chapter 17 Solutions

Organic Chemistry: Principles And Mechanisms (second Edition)

Ch. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - Prob. 17.14PCh. 17 - Prob. 17.15PCh. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - Prob. 17.18PCh. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Prob. 17.22PCh. 17 - Prob. 17.23PCh. 17 - Prob. 17.24PCh. 17 - Prob. 17.25PCh. 17 - Prob. 17.26PCh. 17 - Prob. 17.27PCh. 17 - Prob. 17.28PCh. 17 - Prob. 17.29PCh. 17 - Prob. 17.30PCh. 17 - Prob. 17.31PCh. 17 - Prob. 17.32PCh. 17 - Prob. 17.33PCh. 17 - Prob. 17.34PCh. 17 - Prob. 17.35PCh. 17 - Prob. 17.36PCh. 17 - Prob. 17.37PCh. 17 - Prob. 17.38PCh. 17 - Prob. 17.39PCh. 17 - Prob. 17.40PCh. 17 - Prob. 17.41PCh. 17 - Prob. 17.42PCh. 17 - Prob. 17.43PCh. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - Prob. 17.46PCh. 17 - Prob. 17.47PCh. 17 - Prob. 17.48PCh. 17 - Prob. 17.49PCh. 17 - Prob. 17.50PCh. 17 - Prob. 17.51PCh. 17 - Prob. 17.52PCh. 17 - Prob. 17.53PCh. 17 - Prob. 17.54PCh. 17 - Prob. 17.55PCh. 17 - Prob. 17.56PCh. 17 - Prob. 17.57PCh. 17 - Prob. 17.58PCh. 17 - Prob. 17.59PCh. 17 - Prob. 17.60PCh. 17 - Prob. 17.61PCh. 17 - Prob. 17.62PCh. 17 - Prob. 17.63PCh. 17 - Prob. 17.64PCh. 17 - Prob. 17.65PCh. 17 - Prob. 17.66PCh. 17 - Prob. 17.67PCh. 17 - Prob. 17.68PCh. 17 - Prob. 17.69PCh. 17 - Prob. 17.70PCh. 17 - Prob. 17.71PCh. 17 - Prob. 17.72PCh. 17 - Prob. 17.73PCh. 17 - Prob. 17.74PCh. 17 - Prob. 17.75PCh. 17 - Prob. 17.76PCh. 17 - Prob. 17.77PCh. 17 - Prob. 17.78PCh. 17 - Prob. 17.79PCh. 17 - Prob. 17.80PCh. 17 - Prob. 17.81PCh. 17 - Prob. 17.82PCh. 17 - Prob. 17.83PCh. 17 - Prob. 17.84PCh. 17 - Prob. 17.1YTCh. 17 - Prob. 17.2YTCh. 17 - Prob. 17.3YTCh. 17 - Prob. 17.4YTCh. 17 - Prob. 17.5YTCh. 17 - Prob. 17.6YTCh. 17 - Prob. 17.7YTCh. 17 - Prob. 17.8YTCh. 17 - Prob. 17.9YTCh. 17 - Prob. 17.10YTCh. 17 - Prob. 17.11YTCh. 17 - Prob. 17.12YTCh. 17 - Prob. 17.13YTCh. 17 - Prob. 17.14YT
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