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Q: aniline vs acetanilide ( No Answer,   1 Comment )
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?
There is no answer at this time.

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:
Here is aniline structure:

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