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Which of the following reactions proceeds by an S_N2 mechanism?
- CH3Br reacts with OH− to form CH3OH and Br−
- CH3−CH(Br)−CH3 reacts with OH− to give CH3−CH(OH)−CH3
- CH3CH2OH undergoes dehydration to produce CH2=CH2
- (CH3)3C−Br reacts with OH− to form (CH3)3COH and Br−
Correct answer: CH3Br reacts with OH− to form CH3OH and Br−
Solution
CH3Br is a primary (methyl) substrate with no steric hindrance, so its reaction with OH- proceeds cleanly by SN2. Tertiary (CH3)3C-Br goes by SN1, and the dehydration of ethanol is an elimination.
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