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For the reaction CH3Br + Nu− → CH3−Nu + Br−, the nucleophiles A to D give the following decreasing order of reaction rate: [Nu− = (A) PhO−, (B) AcO−, (C) HO−, (D) CH3O−]. Which sequence is correct?

1. A > B > C > D
2. B > D > C > A
3. D > C > A > B
4. D > C > B > A

Correct answer: D > C > B > A

Solution

For SN2 on CH3Br nucleophilicity follows conjugate-acid basicity: CH3O- (pKa ~15.5) > HO- (15.7, but stronger nucleophile here) > PhO- (10) > AcO- (4.8). Order D > C > A > B.

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