The enantiomerically pure halide shown reacts with sodium cyanide in DMSO, which favours a bimolecular substitution. Which structure is the major product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: D

The compound is (S)-2-bromobutane. SN2 proceeds with backside attack, so the configuration is inverted. Because CN outranks the ethyl group exactly as Br did, the descriptor changes from S to R, giving (R)-2-methylbutanenitrile.

Practice Organic Reaction Mechanisms IV: Elimination More on Substitution vs elimination outcome for drawn substrates

Previous questionNext question

More questions on Substitution vs elimination outcome for drawn substrates

The halide shown is used in the reactions below. Select all correct statements. JEE Main level
The halide shown is allowed to solvolyse in an ethanol-water mixture with no added strong base. Select all correct statements. JEE Main level
The compound shown is warmed with dilute aqueous sodium hydroxide. Loss of water gives which major organic product? JEE Main level
The optically active halide shown is stirred in aqueous acetone, where the substitution proceeds by an SN1 mechanism. What is the expected s... JEE Main level
The halide shown has no hydrogen on the carbon next to the carbon bearing bromine. Select all correct statements. JEE Advanced level
The halide shown (axial bromine in the reactive chair) is treated with sodium azide in DMF, a good nucleophile that is only weakly basic. Wh... JEE Advanced level