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Topic: Base Hydrolysis of Ester giving racemic product  (Read 2500 times)

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Offline Penguinone

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Base Hydrolysis of Ester giving racemic product
« on: February 10, 2014, 06:54:39 PM »
Hydrolysis of enantiomerically pure (+) PhCH(Me)COOEt with NaOH in aqueous ethanol gives an extensively racemised acid product. Give a mechanism to explain why.

Attempt: See picture below.

Any help will be greatly appreciated.
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Offline orgopete

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Re: Base Hydrolysis of Ester giving racemic product
« Reply #1 on: February 11, 2014, 09:37:54 AM »
The mechanism contains one element of the answer, however it does not explain how enolization happens. There are two possible materials to enolize. Partial should give a clue as to which it is?
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