Organic 2 Review Problem 183

Organic 2 Review Problem 183 - P REPARATIONS 167 pour the...

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PREPARATIONS 167 pour the pale reddish-orange solution, which may already contain some crystals of p -bromoacetanilide, into a large excess (about 60 ml.) of cold water, whereupon the p -bromoacetanilide will rapidly crystallise out. Stir these crystals thoroughly with the water to eliminate acetic acid, unchanged bromine, etc., and then filter at the pump, wash well with cold water, drain, and finally re- crystallise from rectified spirit. The p -bromoacetanilidc is obtained as colourless crystals, m.p. 167°. Yield, i-o g. /?-Nitroacetanilide, NO 5 C 6 H 4 NHCOCH 35 and p-Nitro- aniline, NO 2 C 6 H 4 NH 2 . Aniline cannot be directly nitrated with the usual nitrating mixture of nitric and sulphuric acid, because considerable charring and oxidation of the aniline occurs. The difficulty may be overcome either by using a very large excess of sulphuric acid, or (better) by protecting the reactive amino group by acetylation, since the acetylamido group, CH 3 CONH -, has the same ortho and para
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This note was uploaded on 09/19/2011 for the course CHM 2211 taught by Professor Castalleano during the Fall '06 term at University of Florida.

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