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Topic: Removing halogen atom from compound  (Read 4229 times)

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Offline Dan7620

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Removing halogen atom from compound
« on: March 05, 2007, 07:37:08 PM »
Hi guys just a quick question regarding a chemistry assignment.  I have the compound 2-chloropropanal, how would i go about removing the chlorine atom to form regular propanal?  I can remove halogen atoms from regular alkyl halides (ie elimanation reaction to form alkene or substitution to form an alcohol), but am unsure about this aldehyde.  ???  Thanks alot  :)

Offline Albert

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Re: Removing halogen atom from compound
« Reply #1 on: March 10, 2007, 04:05:04 AM »
You just have to protect the carbonyl, converting it into an imine. Then, you yield your double bond using a weak base.

The carbonyl is back once you've hydrolyzed the imine with an acid.

Finally, the hydrogenation of the double bond, which will have to be carried out at low temperature (room temperature should be enough) and in mild conditions, to avoid the reduction of the carbonyl group.

Offline Dan7620

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Re: Removing halogen atom from compound
« Reply #2 on: March 11, 2007, 01:32:22 PM »
Excellent, thanks alot!  ;D

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