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JEE MainChemistryAldehydes and Ketones

Cyclohexanecarbaldehyde on reaction with formaldehyde and K ₂ CO ₃ gives compound 'X'. Compound 'X' reacts with KCN and yields compound 'Y', which on acidic hydrolysis gives a stable compound 'Z'. The IUPAC name of compound 'Z' is:

Options

  1. A4-hydroxy-2-oxaspiro[4.5]decan-3-one
  2. B2-hydroxy-2-(1-(hydroxymethyl)cyclohexyl)ethanoic acid
  3. C2-oxaspiro[4.5]decan-3-one
  4. D4-hydroxy-3-oxaspiro[5.5]undecan-2-one

Correct answer

A. 4-hydroxy-2-oxaspiro[4.5]decan-3-one

Step-by-step solution

1. Cyclohexanecarbaldehyde has one -hydrogen. It undergoes a cross-aldol reaction with formaldehyde in the presence of K ₂ CO ₃ to form 1-(hydroxymethyl)cyclohexane-1-carbaldehyde (X). 2. Compound X undergoes nucleophilic addition with KCN to form a cyanohydrin, 2-hydroxy-2-(1-(hydroxymethyl)cyclohexyl)acetonitrile (Y). 3. Acidic hydrolysis of the nitrile group in Y yields an intermediate -hydroxy acid, 2-hydroxy-2-(1-(hydroxymethyl)cyclohexyl)ethanoic acid. 4. This intermediate is unstable and spontaneously underg

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