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Question
Give reasons Acetylation of aniline reduces its activation effect.
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Solution
The lone pair of nitrogen will get involved in resonance with the carbonyl group. Hence it will reduce the activity of benzene ring in aniline. The resonance involved is shown below:
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\[\begin{array}{cc}
\ce{C6H5CHO}\phantom{............}\\
\phantom{........}\ce{+\phantom{......}\ce{->[dil.NaOH][\Delta]}}\phantom{...}\\
\ce{CH3CH2CHO}\phantom{............}
\end{array}\]
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(ii) 
(iii) \[\begin{array}{cc}
\phantom{}\ce{O}\\
\phantom{}||\\
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\end{array}\]
(iv) \[\begin{array}{cc}
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\phantom{}\ce{CH3}\\
\end{array}\]
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\[\ce{CH3-CH2-CHO ->[dil][alkali] Product}\]
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