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20.2 Outline a procedure for separating a mixture

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(g) Aniline + propanoyl chloride<br />

(h) Tetraethylammonium hydroxide<br />

(i)<br />

m-Dinitrobenzene + H 2S<br />

p-Toluidine + Br 2(excess) H2O<br />

NH 3<br />

C 2H 5OH<br />

(j)<br />

Br<br />

20.31 Starting with benzene or toulene, outline a synthesis of each of the following compounds<br />

using diazonium salts as intermediates. (You need not repeat syntheses carried out in earlier of this<br />

proplem.)<br />

(a) p-Fluorotoluene<br />

(b) o-Iodotoluene<br />

(c) p-Cresol<br />

(d) m-Diachlorobenzene<br />

(e) m-(C6H4(CN)2<br />

(f) m-Iodophenol<br />

(g) m-Bromobenzenontrile<br />

(h) 1,3-Dibromo-5-nitrobenzene<br />

(i) 3,5-Dibromoaniline<br />

(j) 3,4,5-TriBromophenol<br />

(k) 3,4,5-Tribromobenzonitrile<br />

(l) 2,6-Dibromobenzoic acid<br />

(m) 1,3-Dibromo-2-iodobenzene<br />

(n) 4-Bromo-2-nitrotoluene<br />

(o) 4-Methyl-3-nitrophenol<br />

O<br />

O<br />

N<br />

Br<br />

O<br />

HN<br />

N<br />

NH 2<br />

NH 2

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