(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?

(a) Explain why a nonsymmetrical ether is not usually prepared by heat

1.	(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?
Answer» Solution :(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.