Dolbier HW Solutions 523

Dolbier HW Solutions 523 - 617 AMINES (c) The amino group...

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( c ) The amino group is at C-2 of a three-carbon chain that bears a phenyl substituent at its terminus. ( d ) Phenylephrine is named systematically as an ethanol derivative. 22.24 ( a ) There are f ve isomers of C 7 H 9 N that contain a benzene ring. ( b ) Benzylamine is the strongest base because its amine group is bonded to an sp 3 -hybridized carbon. Benzylamine is a typical alkylamine, with a K b of 2 3 10 2 5 . All the other isomers are arylamines, with K b values in the 10 2 10 range. ( c ) The formation of N -nitrosoamines on reaction with sodium nitrite and hydrochloric acid is a characteristic reaction of secondary amines. The only C 7 H 9 N isomer in this problem that is a secondary amine is N -methylaniline. ( d ) Ring nitrosation is a characteristic reaction of tertiary arylamines.
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