Oxidation of cholesterol converts the alcohol to a ketone.

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L. G. Wade Jr

Problem 5P Chapter 18

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L. G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 5P

Oxidation of cholesterol converts the alcohol to a ketone. Under acidic or basic oxidation conditions, the C=C double bond migrates to the more stable, conjugated position. Before IR and NMR spectroscopy, chemists watched the UV spectrum of the reaction mixture to follow the oxidation. Describe how the UV spectrum of the conjugated product, cholest-4-en- 3-one, differs from that of cholesterol.

Step-by-Step Solution:
Step 1 of 3

Solution 5P

Oxidation of cholesterol transforms the alcohol functionality into a ketone. Under these oxidizing conditions, the alkene migrates to a more stable, conjugated position. We’re asked to describe how the UV-VIS spectrum of the oxidized product differs from that of the starting material (cholesterol).

The starting material only has one double bond, and it’s not in conjugation with any other unsaturated functional group. This means it’s  to  transition...

Step 2 of 3

Chapter 18, Problem 5P is Solved
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Textbook: Organic Chemistry
Edition: 8
Author: L. G. Wade Jr
ISBN: 9780321768414

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