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Topic: why not haloform reaction give α keto acid?  (Read 2831 times)

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Offline adianadiadi

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why not haloform reaction give α keto acid?
« on: May 01, 2011, 01:28:08 PM »
During the haloform reaction, the base hydrolysis of α,α,α-trihalocarbonyl compound gives the haloform as the final product.

But why not the halogen groups are substituted by the OH- to give a trihydroxy compound which can lose water molecule to give finally α keto acid?

Adi

Offline jake.n

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Re: why not haloform reaction give α keto acid?
« Reply #1 on: May 01, 2011, 07:52:50 PM »
Which carbon is the better electrophile?

Also, if you are looking for a route to an a-keto acid, try adding cyanide to aldehyde and hydrolyze to the secondary a-hydroxy acid, then oxidize.

Offline adianadiadi

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Re: why not haloform reaction give α keto acid?
« Reply #2 on: May 01, 2011, 08:04:50 PM »
Which carbon is the better electrophile?

Also, if you are looking for a route to an a-keto acid, try adding cyanide to aldehyde and hydrolyze to the secondary a-hydroxy acid, then oxidize.

What I feel carbon with 3 halogens must be better electrophile. And that is the question I am asking.

I think the steric factors and the better leaving ability of the CX3 is crucial in understanding.

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