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Which organic chloroalkane undergoes complete inversion of configuration in an S_N2 reaction?

1. (C2H5)2CHCl
2. (CH3)3CCl
3. (CH3)2CHCl
4. CH3Cl

Correct answer: CH3Cl

Solution

SN2 rate decreases with steric hindrance: methyl > primary > secondary > tertiary. CH3Cl (methyl chloride) is the least hindered, so it undergoes the fastest clean SN2 with complete inversion (backside attack).

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