How many isomers are possible (includding geometrical isomers) on monobromination of methyl cyclohexane? Which isomer is in major amount? Compare with monochlorination products.

Explanation

A total of eight isomers (including cis and trans) are possible. The intermediate `Br^(.)` is a sclective radical and attacks the `3^(@)` H giving I as major product. Also, `C1^(.)` is much less selective and the statistical factor plays significant role in determining the product distribution. The monochlorination of methyl cycloexane will also give eight ismers as in monobromination with none dominating.