Dolbier HW Solutions 519

Dolbier HW Solutions 519 - tion 12.7. Reversing the order...

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22.18 The key to this problem is to recognize that the iodine substituent in m -bromoiodobenzene is derived from an arylamine by diazotization. The preparation of m -bromoaniline from benzene has been described in Problem 22.17. All that remains is to write the equation for its conversion to m -bromoiodobenzene. 22.19 The f nal step in the preparation of ethyl m - F uorophenyl ketone is shown in the text example im- mediately preceding this problem, therefore all that is necessary is to describe the preparation of m -aminophenyl ethyl ketone. Recalling that arylamines are normally prepared by reduction of nitroarenes, we see that ethyl m -nitrophenyl ketone is a pivotal synthetic intermediate. It is prepared by nitration of ethyl phenyl ketone, which is analogous to nitration of acetophenone, shown in Section 12.16. The preparation of ethyl phenyl ketone by Friedel Crafts acylation of benzene is shown in Sec-
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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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This note was uploaded on 10/03/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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