An organic compound ‘A’ having the molecular formula C4H8 on treatment with dilute sulphuric acid give another compound ‘B’. B on treatment with conc. HCl and anhydrous zinc chloride gives ‘C’. C on treatment with sodium ethoxide gives back ‘A’. Identify the compound. Write the equations involved.
Explain giving reason although haloalkanes are polar in character, yet they are insoluble in water.
Predict all the alkenes that would be formed by dehydrohalogenation of the following halides with sodium ethoxide in ethanol and identify the major alkene.
(i) 1-Bromo-1-methyl cyclohexane.
(ii) 2-Chloro-2-methyl butane.
(iii) 2, 2, 3-Trimethyl-3-bromopentane.
The given reaction is SN2 reaction. The nucleophile, Nu– approaches the carbon atom on the side opposite from the halogen and forms new covalent bond with the carbon. This is because KCN is an ionic compound, K+ [C ≡ N]–. Since carbon carrying a lone pair of electrons is more reactive than nitrogen carrying a lone pair, the transition state is formed by the carbon of the cyanide ion forming band with the carbon halogen bond thus,