Dolbier HW Solutions 397

Dolbier HW Solutions 397 - 491 ENOLS AND ENOLATES (b) At...

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At equilibrium, compound B predominates because it is more stable than A. A ketone carbonyl is more stabilized than an aldehyde, and the carbonyl in B is conjugated with the benzene ring. ( b ) The isolated product is the double hemiacetal formed between two molecules of compound A. 18.35 ( a ) The only stereogenic center in piperitone is adjacent to a carbonyl group. Base-catalyzed enol- ization causes this carbon to lose its stereochemical integrity. Both the enolate and enol of piperitone are achiral and can revert only to a racemic mixture of piperitones. ( b ) The enol formed from menthone can revert to either menthone or isomenthone. Only the stereochemistry at the a -carbon atom is affected by enolization. The other stereogenic center in menthone (the one bearing the methyl group) is not affected.
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