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COMEDK · Chemistry · 27. Aldehydes and Ketones

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.

  1. A 2-hydroxy-3-methylpentanal
  2. B 4-hydroxyhexanal
  3. C 3-hydroxy hexanal
  4. D 3-hydroxy-2-methyl-pentanal
Verified Solution

Answer & Solution

Correct Answer

(D) 3-hydroxy-2-methyl-pentanal

Step-by-step Solution

Detailed explanation

Propanal (\(CH_3-CH_2-CHO\)) undergoes self-aldol condensation in the presence of dilute NaOH. The \(\alpha\)-carbon of one propanal molecule is deprotonated by the base to form an enolate ion: \(CH_3-CH_2-CHO + OH^- \rightleftharpoons CH_3-\bar{C}H-CHO + H_2O\) This enolate ion…
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