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QUESTION

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

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.

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.