Chapter 13: Amines

A hydrocarbon ' $\mathrm{A}$ ', $\left(\mathrm{C}_{4} \mathrm{H}_{8}\right)$ on reaction with $\mathrm{HCl}$ gives a compound ' $\mathrm{B}$ ' $\left(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{Cl}\right)$, which on reaction with $1 \mathrm{~mol}$ of $\mathrm{NH}_{3}$ gives compound ' $\mathrm{C}$ ', $\left(\mathrm{C}_{4} \mathrm{H}_{11} \mathrm{~N}\right) .$ On reacting with $\mathrm{NaNO}_{2}$ and $\mathrm{HCl}$ followed by treatment with water, compound ' $\mathrm{C}$ ' yields an optically active alcohol, ' $D$ '. Ozonolysis of ' $A$ ' gives 2 moles of acetaldehyde. Identify compounds 'A' to 'D'. Explain the reactions involved.

A colourless substance ' $\mathrm{A}^{\prime}\left(\mathrm{C}_{6} \mathrm{H}_{7} \mathrm{~N}\right)$ is sparingly soluble in water and gives a water soluble compound ' $\mathrm{B}$ ' on treatment with mineral acid. On reacting with $\mathrm{CHCl}_{3}$ and alcoholic potash 'A' produces an obnoxious smell due to the formation of compound ' $C$ '. Reaction of 'A' with benzenesulphonyl chloride gives compound ' $D$ ' which is soluble in alkali. With $\mathrm{NaNO}_{2}$ and, ' $\mathrm{A}$ ' forms compound ' $\mathrm{E}$ ' which reacts with phenol in alkaline medium to give an orange dye ' $F$ ' Identify compounds ' $A$ ' to ' $F$ '.

Predict the reagent or the product in the following reaction sequence.