JEE MainChemistryHaloalkanes and Haloarenes
An optically active alkyl halide undergoes a nucleophilic substitution reaction. The resulting product mixture is found to be completely optically inactive. Which of the following statements correctly describes the kinetics and the intermediate or transition state of this reaction?
Options
- AThe reaction follows second-order kinetics and proceeds via a pentacoordinate transition state.
- BThe reaction follows first-order kinetics and proceeds via a pentacoordinate transition state.
- CThe reaction follows first-order kinetics and proceeds via a planar carbocation intermediate.
- DThe reaction follows second-order kinetics and proceeds via a planar carbocation intermediate.
Correct answer
C. The reaction follows first-order kinetics and proceeds via a planar carbocation intermediate.
Step-by-step solution
The loss of optical activity from a pure optically active alkyl halide indicates that racemisation has occurred. Racemisation is the characteristic stereochemical outcome of an S _ N 1 reaction. The S _ N 1 mechanism is a two-step process that follows first-order kinetics, where the rate-determining step is the formation of a planar carbocation intermediate. The nucleophile can then attack this planar carbocation from either face with roughly equal probability, leading to a racemic mixture. Answer: The reaction fol