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Question
An organic compound with molecular formula \[\ce{C7H7NO2}\] exists in three isomeric forms, the isomer ‘A’ has the highest melting point of the three. ‘A’ on reduction gives compound ‘B’ with molecular formula \[\ce{C7H9N}\]. ‘B’ on treatment with \[\ce{NaNO2/HCl}\] at 0-5° C to form compound ‘C’. On treating C with \[\ce{H3PO2}\], it gets converted to D with formula \[\ce{C7H8}\], which on further reaction with \[\ce{CrO2Cl2}\] followed by hydrolysis forms ‘E’ \[\ce{C7H6O}\]. Write the structure of compounds A to E. Write the chemical equations involved.
Solution
Compound A is p-methylnitrobenzene
Compound B is p- methylbenzenamine
Compound C is p-methylbenzenediazoiumchloride
Compound D - Toluene
Compound E - Benzaldehyde
The chemical reactions involved are
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