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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Penguinone on February 10, 2014, 06:54:39 PM

Title: Base Hydrolysis of Ester giving racemic product
Post by: Penguinone 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.

Title: Re: Base Hydrolysis of Ester giving racemic product
Post by: orgopete 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?