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Organic Chemistry | 7th Edition | ISBN: 9781269406772 | Authors: Paula Yurkanis Bruice
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Explain why the hydrogen and the methyl substituent are

Chapter 28, Problem 20P

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QUESTION:

Problem 20P

Explain why the hydrogen and the methyl substituent are trans to one another after photochemical ring closure of provitamin D3 to form 7-dehydrocholesterol.

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QUESTION:

Problem 20P

Explain why the hydrogen and the methyl substituent are trans to one another after photochemical ring closure of provitamin D3 to form 7-dehydrocholesterol.

ANSWER:

Solution 20P

Step 1 of 2

The ring closure of provitamin D3 to form 7-dehydrocholesterol happens under photochemical conditions.

According to Woodward-Hoffmann rules.

The system with odd numbered -bonds undergoes conrotatory mode under photochemical conditions.

In this ring closure provitamin D3 undergoes conrotatory mode of conversion to form 7 dehydro cholestrol and the methyl and hydrogens attached to two ends of the system are in “Z”configuration.

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