Chapter 24

An organic compound \(X\), on analysis gives \(24.24\) per cent carbon and \(4.04\) per cent hydrogen. Further, sodium extract of \(1.0 \mathrm{~g}\) of \(X\) gives \(2.90 \mathrm{~g}\) of silver chloride with acidified silver nitrate solution. The compound \(X\) may be represented by two isomeric structures, \(Y\) and \(Z\). \(Y\) on treatment with aqueous potassium hydroxide solution gives a dihydroxy compound while \(Z\) on similar treatment gives ethanal. Find out the molecular formula of \(X\) and give the structures of \(Y\) and \(Z\).

What effect should the following resonance of vinyl chloride have on its dipole moment? \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{Cl} \longleftrightarrow \mathrm{CH}_{2}^{-}-\mathrm{CH}=\mathrm{Cl}^{+}\)

Write the structure of all the possible isomers of dichloroethene. Which of them will have zero dipole moment?

(a) Show by chemical equations only, how you would prepare the following from the indicated starting materials. Specify the reagents in each step of the synthesis. (i) Hexachlorethane, \(\mathrm{C}_{2} \mathrm{Cl}_{6}\), from calcium carbide. (ii) Chloroform from carbon disulphide. (b) Give one chemical test which would distinguish between \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}\) from \(\mathrm{CHCl}_{3}\).