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Because 2- methylcyclohexanol is a secondary alcohol (2 R- groups) and can be oxidized to a ketone quite easity whereas 1- methylcyclohexanol is a tertiary alcohol (3 R- groups) and is not easily oxidized. Tertiary alcohols in general are very difficult to oxidize.

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Q: Why does bleach oxidize 2-methylcyclohexanol but not 1-methylcyclohexanol?
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