Question

13. Which of the following statements correctly describes the stereochemical outcome of the reaction indicated below? NH CH3COOH, Dean-Stark trap, heat at reflux (A) A single imine without any stereogenic centers will be generated in the above reaction. (B) A single enantiomer of an optically active enamine will be generated in the above reaction. (C) A racemic mixture of enamines will be generated in the above reaction. (D) A diastereomeric mixture of enamines will be generated in the above reaction. (E) A diastereomeric mixture of a carbinolamine (also known as a hemiaminal) will be the final product isolated in this reaction.

Answer 1

SOLN 13

This is a reaction of cyclohexanone with pyrrolidine which is a secondary amine, it result in the formation of enamine. enamine carbon is sp2 hence planar it will not result in the formation of any chiral center .

since we have equatorial methyl in the cyclohexanone ring, after formation of enamine it will become new chiral center but since Me have a fixed stereochemistry , it will form single enantiomer which will be optically active

only single enantiomer (R)-1-(5-methylcyclohex-1-en-1-yl)pyrrolidine

Hence correct option is B

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