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Isomers of Dimethylcyclohexanediol

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How many isomers of dimethylcyclohexanediol could you get from complete hydroboration-oxidation of 1,4-dimethyl-1,4-cyclohexadiene? Draw them all.

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When borane (BH3) adds to a double bond, the hydrogen (as a hydride ion, H-) becomes bonded to the more substituted carbon. The result is what appears to be anti-Markovnikov addition. In fact, steric hindrance plays a role too. The more sterically hindered the more substituted carbon is, the better yield of the ...

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