In the Williamson ether synthesis, an alkoxide reacts with an alkyl halide to gi

Question

In the Williamson ether synthesis, an alkoxide reacts with an alkyl halide to give an ether. R-O:^- + R?-X:---> R-O-R? + :X:^- You are in charge of a research group for a large company, Ethers Unlimited, and you have been assigned the task of synthesizing i-butyl methyl ether, (CH3)3C-O-CH3. You have decided to delegate this task to two of your staff chemists. One chemist, Ima Smart, allows (CH3)3C-O:^- to react with CH3-I and indeed obtains a good yield of the desired ether. The other chemist, Notso Bright, allows CH3O:^- to react with (CH3)3C-Br. To his surprise, no ether was obtained. Before terminating Notso Bright?s employment, explain to him why his reaction failed.

Explanation / Answer

ether formtion from Williumson ether synthesis involves SN2 type mechanism which requires less hindered alkyl halide and strong base. but in Notso Bright method, the alkyl halide provided was very stericlly hindered and so SN2 type mechanism mostly does not occur.

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