Question

An organic compound $\left(A\right)$ of molecular formula $C_7{H}_8$ on treatment with $C{l}_2$ in the presence of sunlight gives compound $\left(B\right)$ of molecular formula $C_7{H}_{7}Cl$. Compound $\left(B\right)$ reacts with $Zn-Cu$ couple to give back compound $\left(A\right)$. Compound $\left(B\right)$ on mild oxidation with $Cu(N{O}_3{)}_2$ gives $\left(C\right)$ of molecular formula $C_7{H}_{6}O$. Identify $\left(A\right),\left(B\right),$ and $\left(C\right)$. Explain the reactions.

Answer 1

$\left(A\right)$ is toluene $\left(C_7{H}_8\right)$

$A\to B$ is side chair photo chlorination

Reduction of alkyl halides to alkene $Ph-C{H}_2-Cl\to Ph-C{H}_2$

This reaction is known as mild oxidation by the use of metal nitrales