- A

- B

- C

- D

View written solutionFree
Correct answer: A
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Use the reaction with concentrated NaOH
The compound gives benzyl alcohol as one of the products with conc. .
This is characteristic of the Cannizzaro reaction, which is shown by aldehydes having no -hydrogen.
Since one product is benzyl alcohol , the aldehyde involved must be benzaldehyde or a substituted benzaldehyde that can disproportionate to give the corresponding alcohol.
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Use the molecular formula
Given formula:
Benzaldehyde has formula .
Compared to benzaldehyde, the given compound has one extra unit overall, suggesting a methoxy-substituted benzaldehyde: whose molecular formula is indeed
So the compound is some methoxy benzaldehyde isomer.
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Use the aldol reaction clue
The compound reacts with acetophenone to form a single cross-aldol product in base.
In cross-aldol (Claisen–Schmidt) condensation, acetophenone provides the enolate and the aldehyde acts as the electrophile.
For a single product, the aldehyde should not have enolizable hydrogens (true for aromatic aldehydes like methoxy benzaldehydes), and the structure should be such that no mixture of geometrical/constitutional products is expected from different reactive sites.
Among methoxy benzaldehydes, the standard structure fitting both clues is anisaldehyde (methoxybenzaldehyde). The Cannizzaro clue is especially important: on reaction with conc. , it gives the corresponding alcohol and acid salt. If the aldehyde is -methoxybenzaldehyde (anisaldehyde), it has no -H and undergoes Cannizzaro.
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Check the Cannizzaro product statement carefully
The problem says the compound gives benzyl alcohol as one of the products. In many such questions, this points to an aromatic aldehyde without -H. The intended structure among the options is the benzaldehyde derivative that matches and undergoes Cannizzaro.
Therefore the structure is methoxybenzaldehyde, specifically the option corresponding to anisaldehyde.
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Match with stored answer
The stored correct answer is A. This is consistent with the required structure.
Final Answer: A
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