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Subject:
aniline vs acetanilide
Category: Science > Chemistry Asked by: orgogirl-ga List Price: $3.50 |
Posted:
27 Jun 2006 09:06 PDT
Expires: 27 Jul 2006 09:06 PDT Question ID: 741491 |
Why is aniline basic and acetanilide neutral? |
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There is no answer at this time. |
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Subject:
Re: aniline vs acetanilide
From: atozed-ga on 29 Jun 2006 17:59 PDT |
Basicity is due to differences in chemical structure of the 2 compounds. Acetanilide has carbonyl (C=O) which delocalizes the free electrons on nitrogen. It also has phenyl ring which also "uses up" these electons as well. When you say that acetanilide is neutral, that is not strictly speaking correct. It can be protonated by a strong enough acid, hence it can be a base. Aniline only has phenyl ring. It is less basic than amines without the phenyl ring. Amides have much lower pKa or higher pKb (measure of basicity) than amines. Here is acetanilide structure: http://en.wikipedia.org/wiki/Acetanilide Here is aniline structure: http://en.wikipedia.org/wiki/Aniline |
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