Write the structure of the carbinolamine intermediate and the enamine product formed in the reaction of each of the following:
(a) Propanal and dimethylamine, CH3NHCH3
(b) 3-Pentanone and pyrrolidine
(c) Acetophenone and
Sample Solution (a) Nucleophilic addition of dimethylamine to the carbonyl group of propanal produces a carbinolamine:
Dehydration of this carbinolamine yields the enamine:
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