Question 14.4: Which alcohol(s) yield 4-methylhex-2-ene on dehydration? Are...

Which alcohol(s) yield 4-methylhex-2-ene on dehydration? Are there any other alkenes that arise from dehydration of these alcohols?

\underset{\text{4-Methylhex-2-ene}}{\begin{matrix}CH_3\,\,\,\,\,\,\,\,\,\,\, \\ CH_3CH_2\overset{|}{C}HC H=CHCH_3 \end{matrix} }

ANALYSIS The double bond in the alkene is formed by removing —H and —OH from adjacent carbons of the starting alcohol. This removal occurs in two possible ways, depending on which carbon is bonded to the —OH and to the —H.