Synthesizing ethers via acid-catalyzed condensation reactions haslimited usefulness. The conditions (sulfuric acid and heat) arealso conducive to elimination products. Primary alcohols willundergo dehydration to ethers at lower temperatures thandehydration to alkenes. Secondary and tertiary alcohols will givepredominantly alkene products at the same temperature primaryalcohols condense to give ethers. Primary alcohol condensation toethers is also only useful when the ether is symmetric. Thefollowing question is to demonstrate the mess you would get if youtried to synthesize an asymmetric ether via acid-catalyzeddehydration.
What two alcohols would you use if your goal was to synthesize hexyl pentyl ether via acid-catalyzed dehydration of two alcohols?