Which of the following alkyl halides would be the least reactive
substrate in a Williamson ether synthesis (reaction with NaOEt ;
sodium
alkoxides to form ethers)?
Homework Answers
The Williamson Ether synthesis is an SN2 reaction. Remember that since the SN2 reaction proceeds through a single step where the nucleophile performs a “backside attack” on the alkyl halide, the “big barrier” for the SN2 reaction is steric hindrance. The rate of the SN2 reaction was highest for methyl halides, then primary, then secondary, then tertiary.
Here in above options , option (c) is tertiary alkyl halide. Hence, this tertiary alkyl halide in option (c) will be least reactive.
Correct option is (C).
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