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Fundamentals of Organic ChemistryChemistryAldehydes and Ketones

Indane-1,2,3-trione (the anhydrous form of ninhydrin) contains three keto groups, as shown in the structure below. Which of the labelled keto groups is expected to undergo hydration most easily?

Options

  1. A1
  2. B3
  3. C2
  4. DAll are equally hydrated

Correct answer

C. 2

Step-by-step solution

In indane-1,2,3-trione, there are three adjacent keto groups. The reactivity of a carbonyl group towards nucleophilic addition (like hydration) depends on the magnitude of the positive charge (electrophilicity) on the carbonyl carbon. The carbonyl carbon at position 2 is flanked by two highly electron-withdrawing carbonyl groups at positions 1 and 3. Due to the strong -I (inductive) effect of these adjacent carbonyl groups, the carbon at position 2 becomes highly electron-deficient and thus highly electrophilic. On

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