November 17, 2024, 05:29:02 AM
Forum Rules: Read This Before Posting


Topic: why not haloform reaction give α keto acid?  (Read 2834 times)

0 Members and 1 Guest are viewing this topic.

Offline adianadiadi

  • Regular Member
  • ***
  • Posts: 51
  • Mole Snacks: +0/-6
    • AdiChemistry: An Online Resource of Chemistry Study Material
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

  • Regular Member
  • ***
  • Posts: 53
  • Mole Snacks: +1/-1
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

  • Regular Member
  • ***
  • Posts: 51
  • Mole Snacks: +0/-6
    • AdiChemistry: An Online Resource of Chemistry Study Material
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.

Sponsored Links