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Organic Chemistry | 7th Edition | ISBN: 9781269406772 | Authors: Paula Yurkanis Bruice
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Explain why the hydrogens of the C-8 methyl group are more

Chapter 24, Problem 7P

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QUESTION:

Problem 7P

Explain why the hydrogens of the C-8 methyl group are more acidic than those of the C-7 methyl group.

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QUESTION:

Problem 7P

Explain why the hydrogens of the C-8 methyl group are more acidic than those of the C-7 methyl group.

ANSWER:

Solution 7P

2

According to Bronsted-Lowry theory an acid is a compound which can donate proton. The species generated from an acid molecule by removal of a proton is called the conjugate base of that acid.

The acidity of a specific proton in a compound can be judged from the stability of the conjugate base produced.

When a proton is abstracted from the C-8 methyl group the carbanion produced is resonance stabilized through extensive conjugation. Hence hydrogens of C-8 methyl group are acidic.

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