Dolbier HW Solutions 514

Dolbier HW Solutions 514 - in 90% yield. The starting...

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22.11 For each part of this problem, keep in mind that aromatic amines are derived by reduction of the corresponding aromatic nitro compound. Each synthesis should be approached from the standpoint of how best to prepare the necessary nitroaromatic compound. ( b ) The para isomer of isopropylaniline may be prepared by a procedure analogous to that used for its ortho isomer in part ( a ). After separating the ortho, para mixture by distillation, the nitro group of p -isopropyl- nitrobenzene is reduced to yield the desired p -isopropylaniline. ( c ) The target compound is the reduction product of 1-isopropyl-2,4-dinitrobenzene. This reduction is carried out in the same way as reduction of an arene that contains only a single nitro group. In this case hydrogenation over a nickel catalyst gave the desired product
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Unformatted text preview: in 90% yield. The starting dinitro compound is prepared by nitration of isopropylbenzene. 80 8 C HNO 3 , H 2 SO 4 Isopropylbenzene CH(CH 3 ) 2 1-Isopropyl-2,4-dinitrobenzene (43%) CH(CH 3 ) 2 NO 2 NO 2 reduce CH(CH 3 ) 2 NH 2 NH 2 4-Isopropyl-1,3-benzenediamine CH(CH 3 ) 2 NO 2 NO 2 1-Isopropyl-2,4-dinitrobenzene H 2 , Ni; or 1. Fe, HCl; 2. HO 2 or 1. Sn, HCl; 2. HO 2 CH(CH 3 ) 2 NH 2 CH(CH 3 ) 2 NO 2 1 (CH 3 ) 2 CHCl AlCl 3 HNO 3 H 2 SO 4 CH(CH 3 ) 2 NO 2 p-Isopropylnitro-benzene CH(CH 3 ) 2 NO 2 o-Isopropylnitro-benzene CH(CH 3 ) 2 Isopropybenzene Benzene NH 2 Ar NO 2 Ar H Ar (Ar 5 substituted aromatic ring) 608 AMINES...
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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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