Essential Organic Chemistry (3rd Edition)
Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 20, Problem 17P

(a)

Interpretation Introduction

Interpretation:

The product formed when cholesterol reacts with hydrogen in presence of palladium-carbon has to be drawn.

(a)

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Cholesterol with hydrogen:

Essential Organic Chemistry (3rd Edition), Chapter 20, Problem 17P , additional homework tip  1

Cholesterol reacts with hydrogen in presence of palladium-carbon to reduce double bond to single bond and forms cholestanol.  Therefore, the product obtained is cholestanol which is shown in the above scheme.

(b)

Interpretation Introduction

Interpretation:

The product formed when cholesterol reacts with acetyl chloride has to be drawn

(b)

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Cholesterol with acetyl chloride:

Essential Organic Chemistry (3rd Edition), Chapter 20, Problem 17P , additional homework tip  2

Cholesterol reacts with acetyl chloride in which acetylation reaction take place at hydroxyl group and forms cholesteryl acetate.  Therefore, the product obtained is cholesteryl acetate which is shown in the above scheme.

(c)

Interpretation Introduction

Interpretation:

The product formed when cholesterol reacts with sulfuric acid followed by heating has to be drawn.

(c)

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Cholesterol with sulfuric acid:

Essential Organic Chemistry (3rd Edition), Chapter 20, Problem 17P , additional homework tip  3

Cholesterol reacts with sulfuric acid in which removal of water molecule take place and forms cholestene.  Therefore, the product obtained is cholestene which is shown in the above scheme.

(d)

Interpretation Introduction

Interpretation:

The product formed when cholesterol reacts with water in presence of acid has to be drawn.

(d)

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Cholesterol with water:

Essential Organic Chemistry (3rd Edition), Chapter 20, Problem 17P , additional homework tip  4

Cholesterol reacts with water in presence of water in which removal of water molecule take place and forms desired product.  Therefore, the product obtained is is shown in the above scheme.

(e)

Interpretation Introduction

Interpretation:

The product formed when cholesterol reacts with peroxy acid has to be drawn

(e)

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Explanation of Solution

Cholesterol with peroxy acid:

Essential Organic Chemistry (3rd Edition), Chapter 20, Problem 17P , additional homework tip  5

Cholesterol reacts with peroxy acid in presence of water in which reaction take place at double bond and forms epoxide product.  Therefore, the epoxide product obtained is shown in the above scheme.

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