ORGANIC CHEMISTRY (LL)-W/ACCESS
ORGANIC CHEMISTRY (LL)-W/ACCESS
10th Edition
ISBN: 9781259717536
Author: Carey
Publisher: MCG
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Chapter 21, Problem 58DSP
Interpretation Introduction

Interpretation:

The major organic product(s) of the given reaction is to be predicted.

Concept Introduction:

Carboxylic acids in presence of the reagent NaH, THF followed by LDA yields the acid dianions in which the negative charge resides on both the oxygen atoms in the original carboxylic acid.

However, the dianion formed has carbanionic character and it can potentially act as a nucleophile to create a new carbon-carbon single bond.

The dianions formed when treated with primary or methyl halides the alkylation of acid dianions takes place.

The new carbon-carbon single bond in these reactions is formed between the carbon atom bearing the halogen atom in the given alkyl halide and the alpha carbon atom in the given carboxylic acid.

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Chapter 21 Solutions

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