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Topic: Basicity  (Read 4329 times)

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Offline orgoclear

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Basicity
« on: November 30, 2009, 11:09:05 AM »
How do you consider the basicity of the following anilines

The rest is obvious .. I just have doubts in p-methyl aniline and p-ethyl aniline

Ethyl is more electron releasing than methyl. So, should'nt p-ethyl one be more basic.. The answer is given exactly the opposite

I assume that it is due to the fact that -CH3 has more Hyperconjugative Hydrogen. But as a whole -C2H5 is more electron releasing or am i wrong

Offline stewie griffin

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Re: Basicity
« Reply #1 on: November 30, 2009, 12:57:40 PM »
To be honest I don't think I could of predicted either way with regard to the methyl and ethyl compounds.  ???

Offline movies

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Re: Basicity
« Reply #2 on: November 30, 2009, 01:16:59 PM »
I think the ethyl one should be more basic for exactly the reason you said.  I doubt the difference is very large though.  Where did you see an answer that contradicts that?

Offline orgoclear

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Re: Basicity
« Reply #3 on: December 01, 2009, 01:23:39 AM »
Where did you see an answer that contradicts that?

It was a question in one of the B.Tech entrance exams here. and the answer provided was that p-methylaniline was most basic.

Although I have searched on the web a bit which seems to indicate that I was right,
pKa of p-methylaniline = 4.85
pKa of p-ethylaniline = 5.03

I doubt the difference is very large though.

It is not too large I guess

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