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The racemization process described in the previous problem

Chapter 22, Problem 22.66

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QUESTION:

The racemization process described in the previous problem also occurs in acidic conditions. Draw a mechanism for the racemization process in aqueous acid.

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QUESTION:

The racemization process described in the previous problem also occurs in acidic conditions. Draw a mechanism for the racemization process in aqueous acid.

ANSWER:

Step 1 of 5

This exercise tells us that when optically active (S)-2-methylcyclopentanone is treated with aqueous acid, the compound loses its optical activity. We are asked to explain this observation and to draw a mechanism that shows how racemization occurs.

The mechanism of the reaction as follows:

(S)-2-methylcyclopentanone under the acid condition the carbonyl oxygen is protonated.

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