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Topic: acidity of ethane and ethene  (Read 9045 times)

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Offline abcc

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acidity of ethane and ethene
« on: October 25, 2006, 01:58:24 AM »
which is more acidic , ethane or ethene ?? ???
and WHY?
THX

Offline Yggdrasil

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Re: acidity of ethane and ethene
« Reply #1 on: October 25, 2006, 02:46:41 AM »
Hint: The carbons in ethane are sp3 hybridized, but the carbons in ethene are sp2 hybridized.  Does this give you any insight into which is more acidic?

Offline abcc

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Re: acidity of ethane and ethene
« Reply #2 on: October 25, 2006, 05:58:03 AM »
Hint: The carbons in ethane are sp3 hybridized, but the carbons in ethene are sp2 hybridized.  Does this give you any insight into which is more acidic?
i still havn't any idea~
can you explain more  ;)
confused :'(
thxthx

Offline Dan

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Re: acidity of ethane and ethene
« Reply #3 on: October 25, 2006, 08:52:25 AM »
think about which orbital the -ve charge will reside in in each case.
My research: Google Scholar and Researchgate

Offline abcc

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Re: acidity of ethane and ethene
« Reply #4 on: October 25, 2006, 10:08:44 AM »
think about which orbital the -ve charge will reside in in each case.
ooooooo
ethane is more acidic ~
is it becoz the -ive charge ( lone pair e-) donate to the p-orbital of the another carbon ???
it is just similiar to the hyperconjuncation effect :o
thxthxthx

Offline tamim83

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Re: acidity of ethane and ethene
« Reply #5 on: October 25, 2006, 12:03:21 PM »
Um, not quite.  Think a bit harder about the hybridization

Offline Yggdrasil

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Re: acidity of ethane and ethene
« Reply #6 on: October 25, 2006, 02:20:49 PM »
Hint #2:  For a molecular orbital you can define a property called the "s-character" of the orbital (for example, sp3 has 1/4 s-character since it is composed of 1 s-orbital and 3 p-orbitals, while an sp orbital has an s-character of 1/2).  Molecular orbitals with different s-characters will have different electronegativities.  Given what you know about s and p orbitals (which one holds on to electrons more strongly?), how do you think s-character affects the electronegativity of the orbital?  Once you figure that out, it should be clear why ethene is more acidic.

Offline abcc

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Re: acidity of ethane and ethene
« Reply #7 on: October 25, 2006, 06:43:32 PM »
thxq, Big HELP ;)

Offline Dan

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Re: acidity of ethane and ethene
« Reply #8 on: October 25, 2006, 06:51:40 PM »
So what answer did you decide on?
My research: Google Scholar and Researchgate

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