Question

A compound ‘A’ with molecular formula C₄H₁₀O is unreactive towards sodium metal. it does not add Bromine water and does not react with NaHSO₃ solution. On refluxing ‘A’ with excess of HI, it gives ‘B’ which reacts with aqueous NaOH to form ‘C’. ‘C’ can be converted into ‘B’ by reacting with red P and I₃ . ‘C, on treating with conc. H₂SO₄ forms ‘D’. ‘D’ decolounses bromine water. Identify A to D and write the reactions involved.

Answer 1

‘A’ is not an alcohol therefore it does not react with sodium metal. ‘A’ is also not an aldehyde or a ketone as it does not react with NaHSO₃. ‘A’ is not an unsaturated hydrocarbon as it does not add Br₂ (aq). So, it is likely to be a ether.