The ketone shown is allowed to react with each reagent below under suitable conditions. Select the reagent(s) that give a product containing a C=N bond.

A $NH X_{2} OH$
B $NH X_{2} NH X_{2}$
C $(CH X_{3}) X_{2} NH$
D $CH X_{3} OH / H X^{+}$

Answer: A, B

Hydroxylamine gives an oxime and hydrazine gives a hydrazone; both contain C=N. Dimethylamine is a secondary amine and would give an enamine (C=C-N), not a C=N bond. Methanol with an acid catalyst gives a ketal, which contains only C-O single bonds.

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