EXERCISE-4

Find the product in following reaction:

Suggest the product of the reactions:

When $\mathrm{A}$ (given below) reacts with $\mathrm{HI}$ products is $\mathrm{B}$ and not $\mathrm{C}.$ Explain.

Isotopic carbon$-14$ in $\left(\mathrm{A}\right)$ appears at new position (as in $\mathrm{B})$ when $\left(\mathrm{A}\right)$ reacts with ${\mathrm{CH}}_3\mathrm{ONa}.$ Explain.

In the following dehydration of diol with ${\mathrm{H}}_3{\mathrm{PO}}_4,$ following product is formed such that isotopic ${}^{18}\mathrm{O}$ goes with ${\mathrm{H}}_2\mathrm{O}.$ Explain.

In the following ${\mathrm{S}}_{\mathrm{N}}1$ reaction :

An organic compound $\left(\mathrm{A}\right)$ composed of $\mathrm{C}, \mathrm{H}$ and $\mathrm{O}$ gives characteristic colour with ceric ammonium nitrate. Treatement of $\left(\mathrm{A}\right)$ with ${\mathrm{PCl}}_5$ gives $\left(\mathrm{B}\right)$, which reacts with $\mathrm{KCN}$ to form $\left(\mathrm{C}\right)$. The reduction of $\left(\mathrm{C}\right)$ with warm $\mathrm{Na}/{\mathrm{C}}_2{\mathrm{H}}_5\mathrm{OH}$ produces $\left(\mathrm{D}\right).$ which on heating gives $\left(\mathrm{E}\right)$ with evolution of ammonia. Pyridine is obtained on treatment of $\left(\mathrm{E}\right)$ with nitrobenzene. Give structure of compounds $\left(\mathrm{A}\right)$ to $\left(\mathrm{E}\right)$ with proper reasoning.

A mixture of two aromatic compounds $\mathrm{A}$ and $\mathrm{B}$ was separated by dissolving in chloroform followed by extraction with aqueous $\mathrm{KOH}$ solution. The organic layer containing compound $\mathrm{A}$, when heated with alcoholic solution of $\mathrm{KOH}$ produced a compound $\mathrm{C}\left({\mathrm{C}}_7{\mathrm{H}}_5 \mathrm{N}\right)$ associated with an unplesant odour. The alkaline aqueous layer on the other hand, when heated with chloroform and then acidified gave a mixture of two isomeric compounds $\mathrm{D}$ and $\mathrm{E}$ of molecular formula ${\mathrm{C}}_7{\mathrm{H}}_6{\mathrm{O}}_2$. Identify the compound $\mathrm{A},\mathrm{B},\mathrm{C},\mathrm{D}$ and $\mathrm{E}$ write their structures.