CAREY: ORGANIC CHEMISTRY
CAREY: ORGANIC CHEMISTRY
10th Edition
ISBN: 9781260364002
Author: VALUE EDITION
Publisher: MCG CUSTOM
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Chapter 18, Problem 33P
Interpretation Introduction

Interpretation:

The missing compounds in the given following reaction are to be identified.

Concept introduction:

Ketones undergo Wolff-Kishner reduction to give alkanes. The reaction takes place in basic conditions with the loss of a ketone group.

MCPBA causes the epoxidation of alkenes. It stands for m chloroperoxybenzenzoic acid.

Lithium aluminium hydride is a strong reducing agent that causes the reduction of epoxides to alcohols.

Chromic acid is a strong oxidising agent that causes the oxidation of primary alcohols to carboxylic acids and secondary alcohols to ketones.

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Wolff–Kishner reduction (hydrazine, KOH, ethylene glycol, 130°C) of the compound shown gave compound A. Treatment of compound A with m-chloroperoxybenzoic acid (MCPBA) gave compound B, which on reduction with lithium aluminum hydride gave compound C. Oxidation of compound C with chromic acid gave compound D (C9H14O). Identify compounds A through D in this sequence.
(10pts) Compound A, C10H16, was found to be optically active. On catalytic reduction over a palladium catalyst, 2 equivalents of hydrogen were absorbed, yielding compound B, CioH2o. On ozonolysis of A, two fragments were obtained. One fragment was identified as acetic acid (CHCOOH). The other fragment, compound C, was an optically active carboxylic acid, C8H14O2. Write reactions, and draw the correct structures for A-C, explain your answer in detail.
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Chapter 18 Solutions

CAREY: ORGANIC CHEMISTRY

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