What characteristic stereochemical outcome is observed when an optically active secondary alkyl halide undergoes an substitution reaction?
Answer and explanation
Correct answer: A. Complete inversion of configuration
- Step 1: In an mechanism, the attacking nucleophile approaches from the side directly opposite to the leaving group (backside attack).
- Step 2: This simultaneous bond-forming and bond-breaking event causes a complete inversion of spatial configuration at the asymmetric carbon center (Walden inversion).
Answer
Complete inversion of configuration.
Why not the others: Retention occurs in mechanisms; racemization occurs in reactions via planar carbocations; and meso formation requires internal symmetry planes.
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