JEE Main · 2023 · Shift-IImediumBIO-020

Compound A, C5H10O5, given a tetraacetate with Ac2O and oxidation of A with Br2-H2O gives an acid, C5H10O6. Reduction…

Biomolecules · Class 12 · JEE Main Previous Year Question

Question

Compound \ceA,C5H10O5\ce{A, C5H10O5}, given a tetraacetate with \ceAc2O\ce{Ac2O} and oxidation of \ceA\ce{A} with \ceBr2H2O\ce{Br2-H2O} gives an acid, \ceC5H10O6\ce{C5H10O6}. Reduction of \ceA\ce{A} with \ceHI\ce{HI} gives isopentane. The possible structure of \ceA\ce{A} is: image

Options
  1. a

    Option a

  2. b

    Option b

  3. c

    Option c

  4. d

    Option d

Correct Answera

Option a

Detailed Solution

Step 1: Chain Structure — Since reduction with \ceHI\ce{HI} gives isopentane (a branched five-carbon alkane), the carbohydrate must have a branched carbon skeleton.

Step 2: Identification — The formation of a tetraacetate and an aldopentose structure confirms it has four \ceOH-\ce{OH} groups and one \ceCHO-\ce{CHO} group.

Step 3: Selection — Structure (a) matches the isopentyl arrangement and the functional groups described.

Key Point: \ceHI\ce{HI} reduction is a powerful tool to identify the carbon backbone of sugars.

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Compound A, C5H10O5, given a tetraacetate with Ac2O and oxidation of A with Br2-H2O gives an acid,… (JEE Main 2023) | Canvas Classes