Single correct option
Which combination is the best practical synthesis of ethyl tert-butyl ether, , in good yield?
- A.
- B.
- C. with conc. at
- D.
Show answer and solution
Answer: (B)
Williamson synthesis proceeds by , which needs an unhindered (primary) alkyl halide. With and tert-butyl bromide, the alkoxide acts as a strong base and the tertiary halide undergoes E2 elimination to give 2-methylpropene. Using tert-butoxide with the primary halide ethyl bromide gives substitution. Dehydration of a mixture of alcohols gives a mixture of three ethers (, - and the unsymmetrical ether), and tertiary alcohol mostly dehydrates to alkene.
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