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JEE MainChemistryAldehydes and Ketones

Two isomeric compounds A and B have the molecular formula C ₈ H ₁₀ O and both contain a benzene ring. When treated with Pyridinium Chlorochromate (PCC), compound A forms product C , while compound B forms product D . Product C gives a red precipitate with an alkaline solution of copper sulphate and sodium citrate. Product D gives a yellow precipitate with potassium iodide and sodium hypochlorite, but does not give a

Options

  1. AA = 1-phenylethanol, B = 2-phenylethanol
  2. BA = 2-phenylethanol, B = 1-phenylethanol
  3. CA = 2-methylbenzyl alcohol, B = 1-phenylethanol
  4. DA = 2-phenylethanol, B = 4-ethylphenol

Correct answer

B. A = 2-phenylethanol, B = 1-phenylethanol

Step-by-step solution

Compound A is oxidized by PCC to C , which gives a positive test with alkaline copper sulphate and sodium citrate (Benedict's reagent). This indicates that C is an aliphatic aldehyde, meaning A must be a primary alcohol where the - OH group is not directly attached to the aromatic ring or a benzylic carbon (as benzylic oxidation would yield an aromatic aldehyde, which fails Benedict's test). For the formula C ₈ H ₁₀ O , A is 2-phenylethanol ( C ₆ H ₅ CH ₂ CH ₂ OH ), and C is phenylacetaldehyde ( C ₆ H ₅ CH ₂ CHO ).

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