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(a) Explain why a nonsymmetrical ether i...

(a) Explain why a nonsymmetrical ether is not usually prepared by heating a mixture of ROH and R'OH in acid.
(b) Why is it possible to prepare t-butyl ethyl ether by heating a mixture of t-butanol and ethanol?
(c ) Would you get any di-t-butyl ether from this reaction? Explain.
(d) Can t-butyl ethyl ether be made by heating `H_(2)C=CH(CH_(3))_(2)` and ethanol?

Text Solution

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(a) A mixture of three ethers, i.e. R-O-R, R-O-R and R-O-R is obtained.
(b) When alcohol is `3^(@)`, its oxonium ion easily loses water to form a carbocation, which is solvated by the other `2^(@)` or `1^(@)` alcohol to give the mixed ether preferentially.
This is an example of an `S_(N)1` mechanism.
`Me_(3)COH_(2)^(+)overset(-H_(2)O)rarrMe_(3)C^(+)underset(-H^(+))overset(HOCH_(2)CH_(3))rarrMe_(3)COCH_(2)CH_(3)`
(c ) No. t-Butanol does not solvate the `3^(@)` carbocation readily because of steric hindrance.
(d) Yes, The addition of `H^(+)` to the alkene gives the same `Me_(3)C^(+)` intermediate.
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