organic

sum1????

There is no hindered rotation in any of the substrates, so migratory aptitude holds....I'm getting first one hydride and rest methyl shifts, since cyclohexane isn't hindered by bulky groups, it can rotate itself so that methyl group gets anti conformation to the leaving -OH.
Ring contraction occurs in case of extremely good leaving groups present anti to -OH, such as diazonium ions.