Dolbier HW Solutions 542

Dolbier HW Solutions 542 - 636 AMINES (d ) The key...

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( d ) The key intermediate in the reaction of an amine with nitrous acid is the corresponding dia- zonium ion. Loss of nitrogen from this diazonium ion is accompanied by a hydride shift to form a sec- ondary carbocation. Capture of isopropyl cation by water yields the major product of the reaction, 2-propanol. 22.37 Alcohols are converted to p -toluenesulfonate esters by reaction with p -toluenesulfonyl chloride. None of the bonds to the stereogenic center is affected in this reaction. Displacement of the p -toluenesulfonate leaving group by sodium azide in an S N 2 process and pro- ceeds with inversion of con f guration. Reduction of the azide yields a primary amine. A nitrogen nitrogen bond is cleaved; all the bonds to the stereogenic center remain intact. 22.38 ( a ) The overall transformation can be expressed as RBr RCH 2 NH 2 . In many cases this can be carried out via a nitrile, as RBr RCN RCH 2 NH 2 . In this case, however, the substrate is 1-bromo-2,2-dimethylpropane, an alkyl halide that reacts very slowly in nucleophilic substi-
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