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Q.

An organic compound with molecular formula C9H10O forms 2, 4-DNP derivatives, reduces Tollen’s reagent and undergo canizaro reaction, on vigorous oxidation, it gives 1, 2-Benzene dicarboxylic acid. Structure of aromatic compound is

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a

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b

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c

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d

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answer is B.

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Detailed Solution

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Aromatic Compound with Molecular Formula C9H10O

An organic compound with molecular formula C9H10O:

  • Forms 2,4-DNP derivative, indicating presence of a carbonyl functional group.
  • Reduces Tollens' reagent, confirming it is an aldehyde.
  • Undergoes Cannizzaro reaction, showing it is a non-enolizable aromatic aldehyde.
  • On vigorous oxidation, it yields 1,2-benzenedicarboxylic acid (phthalic acid), indicating two -COOH groups ortho to each other.

From these clues, the aromatic compound structure is:

o-Ethylbenzaldehyde (2-ethylbenzaldehyde) – a benzene ring with an ethyl group at the ortho position relative to the aldehyde.

 

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