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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3bm177

Which statements about D-fructose are correct?

  1. AIn the open-chain form it has three stereocentres.
  2. BIt forms the same osazone as D-glucose.
  3. CIts furanose form arises by attack of the C-5 hydroxyl group on the C-2 carbonyl carbon.
  4. DBromine water readily oxidises it to a six-carbon monocarboxylic acid.

Answer: A, B, C

Open-chain fructose has stereocentres at C-3, C-4 and C-5 (three). Its C-3, C-4, C-5 match glucose so the osazone is identical. The 5-membered furanose ring closes through O-5 adding to the C-2 carbonyl. Br2 water oxidises aldehydes, not ketones, so statement 4 is false.
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