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For an S_N2 substitution, which sequence correctly arranges the following chlorides in decreasing reactivity: CH3Cl, CH3CH2Cl, (CH3)2CHCl, and (CH3)3CCl?

1. CH3Cl > (CH3)2CHCl > CH3CH2Cl > (CH3)3CCl
2. CH3Cl > CH3CH2Cl > (CH3)2CHCl > (CH3)3CCl
3. CH3CH2Cl > CH3Cl > (CH3)2CHCl > (CH3)3CCl
4. (CH3)2CHCl > CH3CH2Cl > CH3Cl > (CH3)3CCl

Correct answer: CH3Cl > CH3CH2Cl > (CH3)2CHCl > (CH3)3CCl

Solution

SN2 rate is governed by backside-attack steric hindrance, so reactivity falls as alpha-substitution rises: CH3Cl > CH3CH2Cl > (CH3)2CHCl > (CH3)3CCl.

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