October 24, 2021, 01:48:00 AM
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Topic: What makes a ketone more acidic than an alkane??  (Read 5454 times)

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Offline saint_john

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What makes a ketone more acidic than an alkane??
« on: September 24, 2010, 01:01:37 AM »
in terms of pKa, the ketone has a much smaller pKa than a regular alkane.

Can someone please explain the difference in the acidities of a ketone and an alkane !
 
Thanks !

Offline Dan

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Offline rohit

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Re: What makes a ketone more acidic than an alkane??
« Reply #2 on: October 02, 2010, 01:09:53 AM »
the ketone contains c=o bond where c+ and 0- partial charge is there and the bond is essentially a 1 and a half bond in resonance and hence the hydrogen is loosely attached as the c adjacent to c=o is -ve  and hence removing h as h+ is easy whereas alkanes are nonpolar and no such way of removing h.thus ketones are more acidic.remember  ease of removing h as h+ is condition for acidity.

Offline james_a

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Re: What makes a ketone more acidic than an alkane??
« Reply #3 on: October 02, 2010, 03:44:06 AM »
in terms of pKa, the ketone has a much smaller pKa than a regular alkane.

Can someone please explain the difference in the acidities of a ketone and an alkane !
 
Thanks !

2 important factors - #1 - electron-withdrawing effect of ketone. #2 - stabilization of conjugate base by resonance.

http://masterorganicchemistry.wordpress.com/2010/09/22/five-key-factors-that-influence-acidity/

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