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JEE Advanced levelSingle correct optionDifficulty 3 of 3bm232

The cyclic sugar shown is converted back to its open-chain form by ring opening. Which statement describes the open-chain sugar?

  1. AAn aldohexose with 4 stereocentres
  2. BA ketohexose with 3 stereocentres
  3. CA ketohexose with 4 stereocentres
  4. DA ketopentose with 3 stereocentres

Answer: B

The ring (five-membered, furanose) contains the former carbonyl carbon C-2, which carries OH, CH2OH and the ring oxygen. Opening gives a C=O at C-2 with six carbons, a ketohexose (D-fructose). The ring form has 4 stereocentres, but in the open chain C-2 is no longer one, leaving 3 (RDKit gives 3).
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