JEE Main Chemistry question

The chloro compound which shows complete stereochemical inversion (Walden inversion) during an Sɴ2 reaction is

(A)CH₃Cl (no stereocentre: three identical H's on the reacting carbon)
(B)(C₂H₅)₂CHCl (two identical ethyl groups on the reacting carbon: no stereocentre)
(C)(CH₃)₃CCl (tertiary; reacts by Sɴ1 with a planar carbocation intermediate, giving racemisation, not clean inversion)
(D)CH₃CH₂CHClCH₃ (2-chlorobutane)Correct

Answer: (D)

Solution

Walden-inversion stereochemistry can only be observed at a genuine stereocentre that reacts cleanly by the concerted, backside-attack Sɴ2 pathway. CH₃Cl has no stereocentre at all (three identical H's); (C₂H₅)₂CHCl has two identical ethyl groups on the reacting carbon, so it too lacks a stereocentre; (CH₃)₃CCl is a

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Question ID VK-139814