The secondary bromide shown is treated with aqueous silver nitrate. The cation first formed rearranges to a more stable one before capture by water. Which structure is the major alcohol?

The compound is 1-bromo-2-methylcyclohexane. Ag+ assists ionisation to a secondary cation at C1. The hydrogen on C2 (which bears the methyl group) shifts with its electron pair to C1, giving the tertiary 1-methylcyclohexyl cation, trapped by water to give 1-methylcyclohexan-1-ol. Ring expansion to a cycloheptyl cation has no driving force.