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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ro271

The diol shown is oxidised with Jones reagent (excess) in one experiment and with PCC (excess) in another. Select ALL correct statements.

  1. AJones reagent gives a keto acid.
  2. BPCC gives a keto aldehyde.
  3. CJones reagent gives a diketone.
  4. DThe Jones product contains no stereocentre.

Answer: A, B, D

The compound is pentane-1,4-diol. Jones reagent oxidises the primary alcohol to the carboxylic acid and the secondary alcohol to the ketone, giving 4-oxopentanoic acid (levulinic acid), which is achiral. PCC stops at the aldehyde and ketone, giving 4-oxopentanal. A diketone is impossible because C1 is a primary alcohol and would have to lose a carbon.
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