Answer :

(i)


• Friedel Crafts reaction takes place in the presence of AlCl3 which is acidic in nature but aniline is basic.


• This leads to aniline forming a salt.


• The acquired positive charge on the nitrogen atom makes it a strong deactivating group and hence aniline does not undergo Friedel Crafts reaction.


(ii)


• In p-Methylaniline, Aniline is substituted with an electron releasing methyl group.


• This increases the electron density on the nitrogen atom making it more available for donation. Thus, p-Methylaniline is basic in nature.


• In the case of p-Nitroaniline, Aniline is substituted with an electron withdrawing nitro group which decreases the electron density on the nitrogen atom.


• This makes the lone pair of electrons on nitrogen less available for donation, making it less basic.


• Thus, p-Methylaniline is more basic than p-Nitroaniline.


(iii)


• The lone pair of electrons on nitrogen atom of aniline shows resonancewith the aromatic ring.


• Also, as discussed above, aniline is basic in nature because it can donate these lone pair of electrons.


• Acetylation of aniline is necessary because else it will react with the catalyst used in electrophilic substitution reactions (AlCl3) which is acidic in nature to form the salt of aniline.


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