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Topic: Converting a carboxylic acid to an alkane  (Read 21139 times)

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Offline HerpDerp

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Converting a carboxylic acid to an alkane
« on: October 08, 2010, 04:05:32 PM »
Can this be done with the Birch reduction, catalytic hydrogenation or the Clemmensen reduction?

Offline ooosh

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Re: Converting a carboxylic acid to an alkane
« Reply #1 on: October 08, 2010, 09:15:56 PM »
No, you can not do it in one step,the methods you listed can not give you an alkane either . 
You may reduce the carboxylic acid to an alcohol(use LiAlH4),then halohydrocarbon,then dehalogenation to alkane.

Offline SVXX

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Re: Converting a carboxylic acid to an alkane
« Reply #2 on: October 09, 2010, 12:44:34 AM »
What about decarboxylation reactions? RCOOH can be converted to R by reacting it with NaOH and CaO. For example,

HCOOH ----> H2 + CO2
CH3COOH -----> CH4 + CO2

This method is elaborated further in http://www.chemguide.co.uk/organicprops/acids/decarbox.html . For other types of decarboxylations, check out the Wikipedia article.
Another important fact that you must know is that certain acids, such as beta-keto acids, decarboxylate simply on warming the compound. This is because of the formation of a favourable six member transition state on warming.
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