1.

A compound 'A' with molecular formula C_4H_10O is unreactive towards sodium metal. It does not add Bromine water and does not react with NaHSO, 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 I_3. 'C' on treating with conc. H_2SO_4 forms 'D'. 'D' decolourises bromine water. Identify A to D and write the reactions involved.

Answer»

Solution :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 `NaHSO_3`. .A. is not an unsaturated hydrocarbon as it does not add `Br_2` (aq). So, it is likely to be a ether.
`underset((C_2H_10O))underset(.A.)(CH_3CH_2OC_2H_5)+ underset(("excess"))(2HI)to underset((.B.))(2C_2H_5I)+ H_2O`
`underset(.B.)(2C_2H_5I)+ underset(("excess"))(NaOH(aq)) to underset(.C.)(C_2H_5OH) + NaI`
`underset(.C.)(C_2H_5OH) OVERSET(P//I_2)to underset(.B.) C_2H_5I`
`underset(.C.)(C_2H_5OH)overset(Conc. H_2SO_4)to underset(.D.)(CH_2=CH_2)`


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