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.

Answer 1

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