Racemic cis-1-bromo-3-methylcyclohexane reacts with $NaSH$ under conditions where only $S_{N} 2$ substitution occurs at the carbon bearing $Br$ . Which statements are correct?

AThe product is trans-3-methylcyclohexane-1-thiol.
BThe product is cis-3-methylcyclohexane-1-thiol.
CThe product mixture is optically inactive.
DThe product consists of exactly one stereoisomer.

Answer: A, C

S_{N} 2

inverts the carbon bearing

Br

, so the cis relationship becomes trans. Trans-1,3-disubstituted cyclohexane with two different groups is chiral, and since the racemic substrate gives both enantiomers in equal amounts, the product is a racemic pair of two stereoisomers, which is optically inactive.

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Racemic cis-1-bromo-3-methylcyclohexane reacts with NaSH under conditions where only SN​2 substitution occurs at the carbon bearing Br. Which statements are correct?

Answer: A, C

More questions on Stereochemical outcomes of substitution

Racemic cis-1-bromo-3-methylcyclohexane reacts with $NaSH$ under conditions where only $S_{N} 2$ substitution occurs at the carbon bearing $Br$ . Which statements are correct?