The enantiopure bromide shown reacts with NaI in acetone (short reaction time, S_N2). A structure drawn without wedges represents the racemic mixture. Which structure is the major product?

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JEE Main levelSingle correct optionDifficulty 2 of 3o3237

The enantiopure bromide shown reacts with $NaI$ in acetone (short reaction time, $S X_{N} 2$ ). A structure drawn without wedges represents the racemic mixture. Which structure is the major product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: D

The compound is (S)-2-bromohexane.

S X_{N} 2

inverts the stereocentre, giving (R)-2-iodohexane, the structure with the opposite wedge; retention, a racemate and elimination to an alkene are not the clean

S X_{N} 2

outcome.

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The enantiopure bromide shown reacts with NaI in acetone (short reaction time, SXN​2). A structure drawn without wedges represents the racemic mixture. Which structure is the major product?

Answer: D

More questions on Stereochemical outcome of substitution on drawn chiral substrates

The enantiopure bromide shown reacts with $NaI$ in acetone (short reaction time, $S X_{N} 2$ ). A structure drawn without wedges represents the racemic mixture. Which structure is the major product?