JEE Main Chemistry question

A substituted aromatic bromide bearing a benzylic stereocentre (Me, Br, H on the side-chain carbon) and ring substituents (Me, F, ) is treated with PhSNa in DMF. The major product is

(A)[product with the configuration at the benzylic carbon inverted relative to the starting bromide, in place of ]Correct
(B)[product with configuration retained at the benzylic carbon]
(C)[product resulting from attack at the ring fluorine instead of the benzylic carbon]
(D)[product resulting from double substitution]

Answer: (A)

Solution

is a strong, soft nucleophile and DMF is a polar aprotic solvent — ideal conditions for a clean bimolecular nucleophilic substitution (). The leaving group here is the benzylic bromide; attacks this benzylic carbon from the face

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Question ID VK-148083