ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
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Chapter 21, Problem 63DSP
Interpretation Introduction

Interpretation:

It is to be determined, if the product which is not capable of cis-trans isomerism, was obtained from dianion A or B shown in the reaction.

Concept Introduction:

Dianion can be prepared from alpha halogenated carboxylic acids by double deprotonation using strong bases such as LDA or KNH2 in ammonia.

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

A 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 carbanion in the dianion of the given carboxylic acid.

Two substituents attached on the ring can be oriented above the ring or below the ring and thus, they will exhibit cis-trans isomerism.

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Chapter 21 Solutions

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