1. The problem statement, all variables and given/known data When trans-2-methylcyclohexanol is subjected to acid-catalyzed dehydration, the major product is 1-methylcyclohexene. However, when trans-1-bromo-2-methylcyclohexane is subjected to dehydrohalogenation, the major product is 3-methylcyclohexene. The attempt at a solution Obviously, this is an E1 mechanism and the hydride shifts occur from either of the adjacent (to the carbocation) carbons in each case. Also, -Br is a much better leaving group than -OH (but I don't know if it's relevant here). The 3° hydrogen in case 2 is more acidic due to the greater -I effect of -Br. Right? How will this affect the outcome of the reaction? How can we account for the different outcomes anyway?