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Question

An organic compound (X) with molecular formula C9H10O gives positive 2,4-DNP and Tollen's tests. It undergoes Cannizzaro reaction and on vigorous oxidation it gives 1,4-benzene dicarboxylic acid. Compound (X) is:

A
benzaldehyde
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B
o-methylbenzaldehyde
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C
p-ethylbenzaldehyde
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D
2,2-dimethylhexanal
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Solution

The correct option is B p-ethylbenzaldehyde
Tollen's tells us there is an aldehyde in the molecule.
After oxidation we got 1,4-benzene dicrboxylic acid that tells that there is group on para.
So the answer is C.

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