Ether formation during the dehydration of secondary alcohols, namely, 2-butanol, 3-pentanol, and 1-cyclopentylethanol, was investigated. Using the proper reaction conditions, the yield of di-2-butyl ether during the dehydration of 2-butanol on alumina can be as high as 40%. That ether is formed by adding an alcohol to the alkene is ruled out by the results from deuterium tracer studies. Results from experiments using S(+)-2-butanol suggest that the formation of di-2-butyl ether occurs by a S(N)2-type mechanism.