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COMEDK20269 May 2026Morning ShiftChemistryAldehydes and KetonesActual

Propanal on reaction with dilute NaOH, undergoes aldol condensation resulting in the formation of a compound A. Identify the correct structure of A and name of the compound.

Options

  1. A2-hydroxy-3-methylpentanal
  2. B4-hydroxyhexanal
  3. C3-hydroxy hexanal
  4. D3-hydroxy-2-methyl-pentanal

Correct answer

D. 3-hydroxy-2-methyl-pentanal

Step-by-step solution

Propanal ( CH₃-CH₂-CHO ) undergoes self-aldol condensation in the presence of dilute NaOH. The -carbon of one propanal molecule is deprotonated by the base to form an enolate ion: CH₃-CH₂-CHO + OH^- CH₃- C H-CHO + H₂O This enolate ion acts as a nucleophile and attacks the electrophilic carbonyl carbon of a second propanal molecule: CH₃-CH₂-CHO + CH₃- C H-CHO CH₃-CH₂-CH(O^-)-CH(CH₃)-CHO Protonation of the resulting alkoxide ion from water yields the aldol product (Compound A): CH₃-CH₂-CH(O^-)-CH(CH₃)-CHO + H₂O CH₃-C

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