[joyb]

"When the (+) enantiomer of PhCH(Me)COOEt is hydrolysised by NaOH in aqueous  ethanol the resulting acid is extensively racemised. Explain."

Why does this occur when the stereogenic centre is not involved in ester hydrolysis? I noticed another stereogenic centre is formed in the mechanism; does this have anything to do with the question?

[Fluorspar]

Could it not be that the OH^- ions remove the hydrogen on the chiral carbon, giving tertiary carbanion that is stabilised both by the ethanol and resonance with the benzene ring?

[Dan]

http://en.wikipedia.org/wiki/Enolate

[joyb]

Enolate? I don't really understand the hint. I can't see anyway that a double bond would be formed?

[joyb]

Carboxylic acids and esters don't undergo keto-enol tautomerisation anyway do they?

[discodermolide]

1,3-diesters can readily undergo tautomerism.
In your case traces of the enol form under basic conditions, which is then re-protonated to give the other enantiomer or the same one back again. As the C=C in the enol is "flat" the proton can be attacked by either the top or the bottom face of the C=C leading to racemisation. 

[orgopete]

Given that the problem depends upon formation of an enolate we presume enolization was covered in your class, but we were not present. The question indicates how hydroxide can cause deprotonation when flanked by a benzene ring and an ester. This is a combined effect similar to acetoacetate or malonate, but not as acidic. I would consider the question unfair if enolization reactions have not been mentioned to this point.

[joyb]

Enolisation has been mentioned, only I thought it only applied to ketones and aldehydes.

[discodermolide]

As you see it also applies to esters.