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Q.

The organic chloro compound, which shows complete stereochemical inversion during an S_N2 reaction, is

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a

(CH₃)₂CHCl

b

(CH₃)₃CCl

c

CH₃Cl

d

(C₂H₅)₂CHCl

answer is C.

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Detailed Solution

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In S_N2 reactions, the nucleophile attacks from the backside resulting in the inversion of molecule.
As we move from 1° alkyl halide to 3° alkyl halide, the crowding increases hindering the approaching nucleophile and at the same time, +I effect increases.
This causes the carbon-bearing halogen less positively polarized.
So, it is less readily attacked by the nucleophile.

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