Question:

Choose the reaction which is not possible:

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Aromatic aldehydes such as benzaldehyde do not reduce Fehling's solution (they do reduce Tollens' reagent).
Updated On: Oct 31, 2026
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The Correct Option is D

Solution and Explanation

Step 1: Option (A) is the Fittig reaction: Ar\(-\)X + 2Na (dry ether) \(\to\) Ar\(-\)Ar + 2NaX, which is possible.
Step 2: Option (B) is nucleophilic aromatic substitution of Cl in 4-nitrochlorobenzene by OH\(-\) (the para NO2 group activates the ring) followed by acidification to 4-nitrophenol, which is possible.
Step 3: Option (C) is the Tollens' test: phenylacetaldehyde (an aliphatic aldehyde) is oxidised to phenylacetate by [Ag(NH3)2]+, which is possible.
Step 4: Option (D) is the Fehling-type oxidation (Cu2+/OH\(-\)) of benzaldehyde; aromatic aldehydes are not oxidised by Fehling's reagent, so this reaction does not occur.
Answer: (D)
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