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Topic: Cannizaro bizzaro  (Read 2813 times)

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Offline aldoxime_amine

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Cannizaro bizzaro
« on: March 07, 2009, 08:14:41 AM »
Nice topic name, no? ;D

I want to verify answer..

Offline Vidya

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Re: Cannizaro bizzaro
« Reply #1 on: March 07, 2009, 09:57:45 AM »
So show the answer ?

Offline aldoxime_amine

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Re: Cannizaro bizzaro
« Reply #2 on: March 09, 2009, 09:55:32 AM »
The nucleophile attacks either of the carbonyls. the resulting hydride attacks the carbonyl adjacent to the one which just got attacked (*), forming the alcohol. Since the remaining carbonyls are meta to the CH2OH and COO- groups, we will consider inductive effect of the carboxylate in preference to that of the CH2OH group(*). Consequently the carbonyl attached to the "carboxylate" ring undergoes attack by the incoming nucleophile.

Please consider the star-marked points, and analyse their validity...

My assumptions:
Excess of base,
Kinetically controlled reaction.

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