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JEE Main levelSingle correct optionDifficulty 2 of 3ro266

The compound shown is treated separately with PCC, with Jones reagent and with . What is the result?

  1. AIt is oxidised to butan-2-one by PCC and to 2-methylbutanoic acid by Jones reagent
  2. BIt is oxidised to a ketone by both PCC and Jones reagent
  3. CNo oxidation or reduction occurs under any of these conditions (the carbinol carbon has no hydrogen)
  4. DIt is oxidised to an aldehyde by PCC and reduced to an alkane by

Answer: C

The compound is 2-methylbutan-2-ol, a tertiary alcohol. Chromium(VI) oxidation of an alcohol needs an alpha C-H on the carbinol carbon, which is absent, and an alcohol has nothing for to reduce. So it is unchanged by all three reagents, unlike primary and secondary alcohols.
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