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Isomers of Dimethylcyclohexanediol

Here is my question. I am working through this and some other problems, and want to compare what I do against what someone who knows a lot more than me on this subject, does.

Please don't do this problem if you are
1. Planning on copying and pasting something from a website (yes, I've had people do that to me here) that doesn't answer my question, and I've probably already seen.
2. Aren't confident in your answer.

Sorry to sound rude, but I've paid for organic chemistry advice on this site that was wrong more than once (or copied incorrectly from a website, as mentioned), so I'd like to avoid that if possible. Thanks for your help.


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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Solution Preview

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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