Cyclohexanone is treated in sequence with (i) pyrrolidine, trace acid, water removed; (ii) $CH X_{3} I$ ; (iii) $H X_{3} O X^{+}$ . The final organic product is

A2-methylcyclohexanone
B1-methylcyclohexan-1-ol
CN-methylcyclohexanamine
Dcyclohexyl methyl ether

Answer: A

The enamine carbon beta to nitrogen is nucleophilic and attacks

CH X_{3} I

in an SN2 step, giving the C-methylated iminium ion. Aqueous acid hydrolyses the iminium ion to the ketone (Stork enamine alkylation), giving 2-methylcyclohexanone.

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

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Cyclohexanone is treated in sequence with (i) pyrrolidine, trace acid, water removed; (ii) CHX3​I; (iii) HX3​OX+. The final organic product is

Answer: A

More questions on Formation of acetals, imines and enamines

Cyclohexanone is treated in sequence with (i) pyrrolidine, trace acid, water removed; (ii) $CH X_{3} I$ ; (iii) $H X_{3} O X^{+}$ . The final organic product is