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Q.
Which alkyl halide exhibits complete racemisation in $S_N1$ reaction?
Haloalkanes and Haloarenes
Solution:
All the molecules undergoing $S _{ N } 1$ reaction shows racemisation as there is formation of 2 types of product in equal amount. Out of all these 4 alkyl halides, $C _{6} H _{5} CH _{2} Cl$ i.e benzylic chloride has the strongest tendency to undergo $S _{ N } 1$ here thus leading to formation of racemic mixture as it contains benzylic carbocation which is most stable.