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Topic: Making carboxylic acid from haloalkane  (Read 6355 times)

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Offline cold

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Making carboxylic acid from haloalkane
« on: October 11, 2016, 02:51:31 PM »
I have this question, where they ask how you can transfer a haloalkane into a carboxylic acid, but where the carbocylic acid have one more carbon than the haloalkane.

Any ideas? Been scratching my head for some time now...


Offline Babcock_Hall

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Re: Making carboxylic acid from haloalkane
« Reply #1 on: October 11, 2016, 03:17:57 PM »
Suppose I said that I was going to take a haloalkane and carbon dioxide and react them together to make a carboxylic acid.  Would that work?  Why or why not?

Offline cold

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Re: Making carboxylic acid from haloalkane
« Reply #2 on: October 11, 2016, 07:37:28 PM »
Are you talking about this?
http://www.chemguide.co.uk/organicprops/haloalkanes/grignard.html

I would say these reactions could be an answer.

If also found a different possible solution:

CH3CH2Br + CN-  :rarrow: Heath :rarrow: CH3 CH2CN + Br

Then, we oxidize the alcohol:

CH3CH2CN + 2H2:rarrow: CH3CH2COOH + NH4-

Would this work? 

Offline Babcock_Hall

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Re: Making carboxylic acid from haloalkane
« Reply #3 on: October 11, 2016, 08:43:06 PM »
Both chemical strategies look fine, except for one potential problem.  Initial hydrolysis of a nitrile should produce a carboxamide.  If you used more extreme hydrolytic conditions, you could produce the free acid from the amide.   Also your terminology is misleading.  The product between a haloalkane and cyanide is a nitrile, not an alcohol, and no oxidation is taking place.

Offline Vidya

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Re: Making carboxylic acid from haloalkane
« Reply #4 on: October 12, 2016, 09:52:42 PM »
I have this question, where they ask how you can transfer a haloalkane into a carboxylic acid, but where the carbocylic acid have one more carbon than the haloalkane.

Any ideas? Been scratching my head for some time now...
Try with Grignard reagent and CO2 as suggested by BabCock
Alkyl halide ---> Grignard reagent + CO2  followed by acidic hydrolysis.


« Last Edit: October 22, 2016, 12:56:24 PM by billnotgatez »

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