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In this question, I know that aniline will not undergo FC reaction as it forms a complex with $\ce {AlCl3}$ and precipitates out. The answer given is (c) and I agree with it. However, the benzene ring with the amide substituent in (d) will be deactivated as the amide substituent will put a positive charge into resonance. So, will it give FC reaction? Should the answer be both c and d?

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  • $\begingroup$ I read that -NHCOCH3 is ortho para direction. By making the resonance structure, option d is meta directing. I am confused. $\endgroup$ – Gautam Jan 15 at 4:13
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    $\begingroup$ Related: chemistry.stackexchange.com/questions/31531/… $\endgroup$ – Tan Yong Boon Jan 15 at 10:15
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    $\begingroup$ AlCl3 reacting with an amide may be difficult compared to amine since lonepair in an amide is in conjugation with carbonyl type group as well as benzene.So FC reaction of benzamide maybe possible $\endgroup$ – Chakravarthy Kalyan Jan 15 at 16:38
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-NHCOCH3 is a slightly activating group due to the lone pair of N which shows +M effect. Hence it is Ortho para directing.

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