The amide shown (stereochemistry not specified) is subjected to the Hofmann bromamide reaction. How many stereoisomers (configurational isomers, optical and geometrical together) does the amine product have? Give your answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 4

The compound shown is 2,3-dimethylpentanamide. Hofmann degradation loses the carbonyl carbon and gives 3-methylpentan-2-amine,

CH X_{3} CH X_{2} CH (CH X_{3}) CH (CH X_{3}) NH X_{2}

. It has two different stereocentres (C2 and C3) and no symmetry, so

2^{2} = 4

stereoisomers.