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20.2 Outline a procedure for separating a mixture

20.2 Outline a procedure for separating a mixture

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Step1<br />

H SO HNO<br />

2N 3H 2 +N2 SO3H Step2<br />

OH<br />

+<br />

+N2 SO3H NaOH<br />

H2O OH<br />

N N<br />

SO3 - Na +<br />

20.16 Butter yellow is a dye once used to color margarine. It has since been shown to be<br />

carcinogenic, and its use in food is no longer permitted. <strong>Outline</strong> a synthesis of butter yellow from<br />

benzene and N, N-dimethylaniline.<br />

N(CH3) 2<br />

Answer:<br />

N(CH 3) 2<br />

CH 3COO - Na +<br />

N N<br />

Butter yellow<br />

HNO3<br />

H 2SO 4<br />

NO 2<br />

N N<br />

Fe<br />

H 3O +<br />

N(CH3)2<br />

NH2 HNO2<br />

20.17 Azo compounds can be reduced to amines by a variety of reagents including stannous<br />

chloride (SnCl2).<br />

SnCl2 Ar N N Ar' ArNH2 + Ar'NH2 This reduction can be useful in synthesis as the following example shows:<br />

4-Ethoxyaniline<br />

SnCl 2<br />

(1) HONO,H 3O +<br />

(2)phenol,OH -<br />

NN +<br />

A(C 14H 14N 2O 2) NaOH,CH 3CH 2Br B(C16H 18N 2O 2)<br />

two molar equivalents of C (C8H11NO) acetic anhydride phenacetin(C10H13NO2) Give a structure <strong>for</strong> phenacetin and <strong>for</strong> the intermediates A,B,C. (Phenacetin, <strong>for</strong>merly used as an

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