What would be the major product obtained from the hydroboration–oxidation of 1-methylcyclohexene?

1 Answer
Feb 17, 2015

The major product will be a racemic mixture of trans-2-methylcyclohexanol.

The reaction amounts to an anti-Markovnikov addition of water to the C=C double bond.

Instead of adding to C-2 of the ring in a Markovnikov reaction, the H adds to C-1, and the OH adds to C-2.

The reaction is also a cis addition, so the H and OH end up on the same side of the ring.

Chemical reaction with a product from manage.meritnation.net.

The product is trans-2-methylcyclohexanol.

Note that the product has two chiral centres. It will be a racemic mixture of (#1R,2R#)- and (#1S,2S#)-2-methylcyclohexanol.