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Topic: Acidity considering the types of bonds  (Read 9446 times)

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Offline SheffieldWednesday4ever

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Acidity considering the types of bonds
« on: September 30, 2009, 06:33:01 PM »
Hey everyone,

my question is which is more stable, CH3-CH2-CH3 or CH2=CH-CH3?

I think the H in the propene is more willing to be given away because its conjugate base will be more stable as it has resonance. Thus, propane is more stable. But I'm kind of lost in this example.

Thanks for reading

Offline gfunk

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Re: Acidity considering the types of bonds
« Reply #1 on: October 01, 2009, 02:47:02 AM »
Are you asking which proton is more acidic - the alkane proton or the alkene proton?  And what do you mean by "stable"?  And are you referring to the neutral molecule or the conjugate base?
Grad Student - Organic Chemistry
University of Alberta

Offline SheffieldWednesday4ever

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Re: Acidity considering the types of bonds
« Reply #2 on: October 01, 2009, 02:01:18 PM »
Sorry,

In short, I'm asking which is a better acid.

Offline lmlh

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Re: Acidity considering the types of bonds
« Reply #3 on: October 02, 2009, 06:41:08 AM »
propaneļ¼Œthe reason as you said

Offline a student

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Re: Acidity considering the types of bonds
« Reply #4 on: October 02, 2009, 11:51:00 AM »
but I think that propen is more acidic because the more s character the C-H bond the more acidity of that hydrogen for example as you know the acidity of alkynes is more than alkenes and they are more acidic than alkanes.

Offline PiBond

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Re: Acidity considering the types of bonds
« Reply #5 on: October 04, 2009, 12:36:04 AM »
Propene is more acidic.  Losing a proton results in a carbanion that can resonate. 

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