JEE Main Chemistry question

Acetaldehyde is not obtained in the reaction

(A)CH₂=CH–CH₃ --(i) O₃ (ii) Zn, H₂O--> (propene ozonolysis giving formaldehyde + acetaldehyde)
(B)An internal alkene --(i) O₃ (ii) Zn, H₂O--> (symmetric cleavage giving two equivalents of acetaldehyde)
(C)HC≡CH + H₂O --HgSO₄/H₂SO₄-->
(D)CH₃COCl + H₂ --Pd–BaSO₄-->Correct

Answer: (D)

Solution

Each of these routes, read at face value, is capable of yielding acetaldehyde: ozonolysis of propene (A) gives formaldehyde + acetaldehyde; symmetric cleavage of an internal but-2-ene-type alkene (B) gives two equivalents of acetaldehyde; Markovnikov (Hg²⁺-catalyzed) hydration of acetylene (C) gives acetaldehyde; and

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Question ID VK-149336