Organic 2 Review Problem 221

Organic 2 Review Problem 221 - P REPARATIONS (CH 3 ),NCH 5...

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PREPARATIONS 205 (CH 3 ),NC«H 5 HOXO — (CH 3 ) 2 NC 6 H 4 NO : H 2 O aniline. The salts of />-nitrosodimethylaniline, such as the hydrochloride, are yellow, whereas the free base is a beautiful green crystalline compound. The colouris presumably dueto a strong contribution by the quinonoid form in which a charge separation has occurred within the molecule: 0IN-C 6 H 4 -N(CH 8 ), «-* 6-N:CeH 4 :N(CH,) t This marked difference in colour between a base and its salts is also exemplified in the case of ammouzobenzene (p. 208). Tertiary amines containing one alkyl and two aryl groups, such as mono- r.iethykliphenylaminc, CI I :i (C (i H 5 ) 2 N, are rarely encountered and arc unim- portant. They usually react with nitrous acid with the insertion of a nitroso group into only one of the two available para positions: monomethyl- diphenylamine thus gives monomethyl -mono -/>- nitroso - diphenylamine, Cl I 3 (C ,.,H ,)NC<;H 4 XO, or A'-methyl-/>-nitrosodiphenylamine. Required:
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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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