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JEE Advanced levelSingle correct optionDifficulty 3 of 3nm209

Open-chain alcohols of formula are treated with acidified potassium dichromate. How many of the isomers can be oxidised (to an aldehyde/acid or ketone) without breaking carbon-carbon bonds? (Structural isomers only.)

  1. A7
  2. B3
  3. C4
  4. D8

Answer: A

Oxidation without C-C cleavage requires at least one H on the carbinol carbon: primary (4) and secondary (3) alcohols qualify; the tertiary alcohol 2-methylbutan-2-ol (1) does not. Total 4 + 3 = 7.
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