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
- A2-hydroxy-3-methylpentanal
- B4-hydroxyhexanal
- C3-hydroxy hexanal
- 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