Q. 745.0( 1 Vote )
Assertion : Acetanilide is less basic than aniline.
Reason : Acetylation of aniline results in decrease of electron density on nitrogen.
Note : In the following questions a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.
A. Both assertion and reason are wrong.
B. Both assertion and reason are correct statements but reason is not correct explanation of assertion.
C. Assertion is correct statement but reason is wrong statement.
D. Both assertion and reason are correct statements and reason is correct explanation of assertion.
E. Assertion is wrong statement but reason is correct statement.
Acetanilide is formed by the acetylation of aniline under the presence of a strong base like pyridine. The lone pair of electrons on nitrogen of acetanilide interacts with oxygen atom due to resonance, resulting in less availability of the electron pair on nitrogen for reaction.
This way, activating effect of –NHCOCH3 group is less than that of amino group and acetanilide is less basic than aniline.
In case of substituted aniline, electron releasing groups increase basic strength whereas electron withdrawing groups like decrease it.
The delocalization of electrons in the Acetanilide is show in below figure;
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