Which of the following reactions give a compound containing a C=N bond as the stable, isolated product (acid catalyst, water removed)?

Aacetaldehyde with $(CH X_{3}) X_{3} N$
Bcyclohexanone with $(C X_{2} H X_{5}) X_{2} NH$
Cbenzaldehyde with $CH X_{3} NH X_{2}$
Dacetone with $C X_{6} H X_{5} NH X_{2}$

Answer: C, D

Primary amines with aldehydes or ketones give imines. Cyclohexanone with a secondary amine gives an enamine, and a tertiary amine has no N-H and cannot form a stable carbinolamine or condensation product.

Practice Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition More on Formation of acetals, imines and enamines

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Which of the following reactions give a compound containing a C=N bond as the stable, isolated product (acid catalyst, water removed)?

Answer: C, D

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