Unformatted text preview: tion 12.7. Reversing the order of introduction of the nitro and acyl groups is incorrect. It is possible to nitrate ethyl phenyl ketone but not possible to carry out a Friedel – Crafts acylation on nitrobenzene, owing to the strong deactivating in F uence of the nitro group. 22.20 Direct nitration of the prescribed starting material cumene (isopropylbenzene) is not suitable, because isopropyl is an ortho, para-directing substituent and will give the target molecule NO 2 CCH 2 CH 3 O Ethyl m-nitrophenyl ketone CCH 2 CH 3 O Ethyl phenyl ketone F CCH 2 CH 3 NH 2 NO 2 Ethyl m-nitrophenyl ketone Ethyl m-fluorophenyl ketone m-Aminophenyl ethyl ketone CCH 2 CH 3 O CCH 2 CH 3 O O I Br m-Bromoiodobenzene Br NH 2 m-Bromoaniline 1. NaNO 2 , HCl, H 2 O 2. KI I Br Br NH 2 m-Bromoiodobenzene m-Bromoaniline AMINES 613...
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- Fall '01
- Organic chemistry, Amine, Benzene, Functional group, Aniline, ethyl phenyl ketone