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Consider the following carboxylic acids: (A) Cyclopent-2,4-diene-1-carboxylic acid (B) Cycloprop-2-ene-1-carboxylic acid (C) Cyclopentanecarboxylic acid (D) But-3-enoic acid The correct increasing order of their rate of decarboxylation on heating with soda lime is:

Options

  1. A(A) < (D) < (C) < (B)
  2. B(C) < (D) < (A) < (B)
  3. C(B) < (C) < (D) < (A)
  4. D(B) < (D) < (C) < (A)

Correct answer

C. (B) < (C) < (D) < (A)

Step-by-step solution

The decarboxylation of carboxylic acids with soda lime ( NaOH and CaO ) proceeds via the formation of a carbanion intermediate. The rate of the reaction is directly proportional to the stability of the carbanion formed after the removal of CO₂ . The intermediate carbanions formed are: (A) Cyclopent-2,4-diene-1-carboxylic acid forms the cyclopentadienyl anion, which is aromatic ( 6 electrons) and exceptionally stable. (B) Cycloprop-2-ene-1-carboxylic acid forms the cyclopropenyl anion, which is anti-aromatic ( 4 ele

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