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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.