The alcohol shown is treated with pyridinium chlorochromate in dichloromethane. What is the outcome?

AIt is oxidised to 2-methylcyclohexanone.
BNo oxidation occurs, because the carbinol carbon has no hydrogen atom.
CThe ring opens to give a keto acid.
DIt is oxidised to an aldehyde.

Answer: B

The alcohol is 1-methylcyclohexan-1-ol, a tertiary alcohol. Oxidation by chromium(VI) needs removal of a hydrogen from the carbinol carbon, and this carbon has none. PCC therefore leaves it unchanged; only forcing conditions that cleave C-C bonds would attack it.

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