EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
2nd Edition
ISBN: 9780393630817
Author: KARTY
Publisher: W.W.NORTON+CO. (CC)
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Chapter 21, Problem 21.89P
Interpretation Introduction

(a)

Interpretation:

How the given synthesis can be carried out is to be suggested.

Concept introduction:

β-Keto esters can be synthesized in a reaction known as Claisen condensation. The α-hydrogen in an carbonyl compound is relatively acidic because of the presence of an adjacent electron withdrawing group. A strong bulky, non-nuclophilic base extracts this proton, resulting in the formation of a carbon nucleophile. The nucleophile attacks and adds to the electrophilic carbon of a carbonyl compound such as an ester to form a tetrahedral intermediate. The elimination of the original alkoxide (acyl) group from this intermediate followed by proton transfers completes the reaction, giving an α-keto ester.

Interpretation Introduction

(a)

Interpretation:

How the given synthesis can be carried out is to be suggested.

Concept introduction:

β-Keto esters can be synthesized in a reaction known as Claisen condensation. The α-hydrogen in an carbonyl compound is relatively acidic because of the presence of an adjacent electron withdrawing group. A strong bulky, non-nuclophilic base extracts this proton, resulting in the formation of a carbon nucleophile. The nucleophile attacks and adds to the electrophilic carbon of a carbonyl compound such as an ester to form a tetrahedral intermediate. The elimination of the original alkoxide (acyl) group from this intermediate followed by proton transfers completes the reaction, giving an α-keto ester.

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Chapter 21 Solutions

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M

Ch. 21 - Prob. 21.11PCh. 21 - Prob. 21.12PCh. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Prob. 21.15PCh. 21 - Prob. 21.16PCh. 21 - Prob. 21.17PCh. 21 - Prob. 21.18PCh. 21 - Prob. 21.19PCh. 21 - Prob. 21.20PCh. 21 - Prob. 21.21PCh. 21 - Prob. 21.22PCh. 21 - Prob. 21.23PCh. 21 - Prob. 21.24PCh. 21 - Prob. 21.25PCh. 21 - Prob. 21.26PCh. 21 - Prob. 21.27PCh. 21 - Prob. 21.28PCh. 21 - Prob. 21.29PCh. 21 - Prob. 21.30PCh. 21 - Prob. 21.31PCh. 21 - Prob. 21.32PCh. 21 - Prob. 21.33PCh. 21 - Prob. 21.34PCh. 21 - Prob. 21.35PCh. 21 - Prob. 21.36PCh. 21 - Prob. 21.37PCh. 21 - Prob. 21.38PCh. 21 - Prob. 21.39PCh. 21 - Prob. 21.40PCh. 21 - Prob. 21.41PCh. 21 - Prob. 21.42PCh. 21 - Prob. 21.43PCh. 21 - Prob. 21.44PCh. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - Prob. 21.47PCh. 21 - Prob. 21.48PCh. 21 - Prob. 21.49PCh. 21 - Prob. 21.50PCh. 21 - Prob. 21.51PCh. 21 - Prob. 21.52PCh. 21 - Prob. 21.53PCh. 21 - Prob. 21.54PCh. 21 - Prob. 21.55PCh. 21 - Prob. 21.56PCh. 21 - Prob. 21.57PCh. 21 - Prob. 21.58PCh. 21 - Prob. 21.59PCh. 21 - Prob. 21.60PCh. 21 - Prob. 21.61PCh. 21 - Prob. 21.62PCh. 21 - Prob. 21.63PCh. 21 - Prob. 21.64PCh. 21 - Prob. 21.65PCh. 21 - Prob. 21.66PCh. 21 - Prob. 21.67PCh. 21 - Prob. 21.68PCh. 21 - Prob. 21.69PCh. 21 - Prob. 21.70PCh. 21 - Prob. 21.71PCh. 21 - Prob. 21.72PCh. 21 - Prob. 21.73PCh. 21 - Prob. 21.74PCh. 21 - Prob. 21.75PCh. 21 - Prob. 21.76PCh. 21 - Prob. 21.77PCh. 21 - Prob. 21.78PCh. 21 - Prob. 21.79PCh. 21 - Prob. 21.80PCh. 21 - Prob. 21.81PCh. 21 - Prob. 21.82PCh. 21 - Prob. 21.83PCh. 21 - Prob. 21.84PCh. 21 - Prob. 21.85PCh. 21 - Prob. 21.86PCh. 21 - Prob. 21.87PCh. 21 - Prob. 21.88PCh. 21 - Prob. 21.89PCh. 21 - Prob. 21.90PCh. 21 - Prob. 21.91PCh. 21 - Prob. 21.92PCh. 21 - Prob. 21.93PCh. 21 - Prob. 21.94PCh. 21 - Prob. 21.95PCh. 21 - Prob. 21.96PCh. 21 - Prob. 21.97PCh. 21 - Prob. 21.98PCh. 21 - Prob. 21.1YTCh. 21 - Prob. 21.2YTCh. 21 - Prob. 21.3YTCh. 21 - Prob. 21.4YTCh. 21 - Prob. 21.5YTCh. 21 - Prob. 21.6YTCh. 21 - Prob. 21.7YTCh. 21 - Prob. 21.8YTCh. 21 - Prob. 21.9YTCh. 21 - Prob. 21.10YTCh. 21 - Prob. 21.11YTCh. 21 - Prob. 21.12YT
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