The substitution reaction of an alkyl halide mainly occurs by the SN1 or SN2 mechanism. Whatever mechanism alkyl halides follow for the substitution reaction to occur, the polarity of the carbon-halogen bond is responsible for these substitution reactions. The rate of SN1 reactions is governed by the stability of the carbocation, whereas for SN2 reactions the steric factor is the deciding factor. If the starting material is a chiral compound, we may end up with an inverted product or a racemic mixture depending upon the type of mechanism followed by the alkyl halide. Cleavage of ethers with HI is also governed by the steric factor and the stability of the carbocation, which indicates that in organic chemistry these two major factors help us in deciding the kind of product formed.
Predict the stereochemistry of the product formed if an optically active alkyl halide undergoes a substitution reaction by the S1 mechanism.
Predict the stereochemistry of the product formed if an optically active alkyl halide undergoes a substitution reaction by the S1 mechanism.
Answer: A racemic mixture is formed (racemisation) — the planar carbocation is attacked from both faces.
Solution
S1 passes through a planar (sp) carbocation. The nucleophile attacks this flat intermediate from either face with almost equal probability, giving both enantiomers.
CBSE Class 12 Board · 2020 · Subjective