Organic Chemistry, 12e Study Guide/Student Solutions Manual
Organic Chemistry, 12e Study Guide/Student Solutions Manual
12th Edition
ISBN: 9781119077329
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 23, Problem 12PP
Interpretation Introduction

Interpretation:

The chemical conversion of cholesterol into the given compounds needs to be summarized.

Concept Introduction:

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Cholesterol is essential for human life. In the human body, it is produced as an intermediate in the biosynthesis of all steroids. It is produced at a much higher rate than is necessary for the synthesis of steroid. In a typical molecule of cholesterol, there is no internal plane of symmetry, and hence every carbon atom is different and each carbon has four different groups.

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A single unit of cholesterol consists of eight tetrahedral chirality centers. This means that there may be 256 stereoisomers of the basic structure of cholesterol, of which there is one correct structure of a single cholesterol unit.

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Reactions of steroids are greatly influenced by steric hindrance. Most steroids prefer reaction at β position, but some reagents attack at α position in case it is sterically favorable (lower steric hindrance).

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Reaction of alkenes with peroxide acids to form epoxides is called epoxidation reaction. In this reaction, the double bond of C=C is converted to an epoxide.

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A chemical reaction between compound and molecular hydrogen in the presence of a catalyst. The addition of hydrogen to double or triple bond is a hydrogenation reaction.

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Hydrogenation of alkenes or alkynes is an addition reaction, which is done in the presence of reducing agents, such as H2/Ni.

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The addition of halogen to double or triple bond is a halogenation reaction.

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