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GATE 2020 CY – Question 17

Organic Chemistry · Biomolecules: Structure, properties and reactions of mono- and di-saccharides, physicochemical properties of amino acids, chemical synthesis of peptides, chemical structure determination of peptides and proteins, structural features of proteins, nucleic acids, lipids, steroids, terpenoids, carotenoids, and alkaloids. · 1 mark · Multiple choice

Find the major product of α-D-glucose with excess acetone under acid catalysis.

Diagram for GATE 2020 CY question 17
  1. Option A in the figure
  2. Option B in the figure
  3. Option C in the figure
  4. Option D in the figure

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Show answer and explanation

Correct answer: (B) Option B in the figure

Explanation

Acid catalyzes reversible ketal formation between acetone and suitably oriented hydroxyl groups. Glucose can equilibrate to its furanose form, allowing favourable 1,2- and 5,6-isopropylidene protection. The product is 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, leaving the 3-OH free. Among the drawn structures, B has this furanose ring and the two correct acetals; the pyranose alternatives and different hydroxyl pairing are incorrect.

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