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JEE Advanced levelSingle correct optionDifficulty 3 of 3g1196

Consider the C-H acidity of I cyclopenta-1,3-diene, II ethyne, III propene (most acidic H) and IV propane (most acidic H). The correct order of decreasing acidity is:

  1. AI > II > IV > III
  2. BI > II > III > IV
  3. CII > I > III > IV
  4. DI > III > II > IV

Answer: B

Cyclopentadiene gives the aromatic cyclopentadienyl anion (pKa about 16). Ethyne gives an sp carbanion (about 25). Propene gives the resonance-stabilised allyl anion (about 43), and propane gives a simple alkyl carbanion (about 50). Hence I > II > III > IV.
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