ochem destroyer # 28

[jdent]

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1-methylcyclohexane treated with Br2 and hv gives 1-bromo, 1-methyl cyclohexane. This is what the destroyer says. Now shouldn't the methyl group be an o/p activator and make it either 1-bromo,2-methylcyclohexane or 1-Bromo,4-methyl cyclohexane?

 

[klutzy1987]

1-methylcyclohexane treated with Br2 and hv gives 1-bromo, 1-methyl cyclohexane. This is what the destroyer says. Now shouldn't the methyl group be an o/p activator and make it either 1-bromo,2-methylcyclohexane or 1-Bromo,4-methyl cyclohexane?

Two things, firstly O/P activation is only by benzene not by cyclohexane. Secondly Br/Hv wouldnt add to benzene anyways it would add in the benzylic position. But you dont even have a benzene.

 

[jdent]

Thanks for the quick clear answer!

 

[Danny289]

1-methylcyclohexane treated with Br2 and hv gives 1-bromo, 1-methyl cyclohexane. This is what the destroyer says. Now shouldn't the methyl group be an o/p activator and make it either 1-bromo,2-methylcyclohexane or 1-Bromo,4-methyl cyclohexane?

think about radical addition reactions and which radical is more stable, and of course we don't have benzene.