Question
A hydrocarbon A (C5H10) on addition of HBr in presence of a peroxide forms (C5H11Br) B which is found to be resolvable into enantiomers. A on addition of HBr in aqueous medium produces C which is an isomer of B but can't be resolved. A on reductive ozonolysis produced (C4H8O) D as one product. D on catalytic reduction with NaBH4 produced E (C4H10O) which is resolvable. E on dehydration with concentrated sulphuric acid produced F (C4H8) which on ozonolysis followed by work-up with Zn−H2O produced two molecules of ethanol. Identify A to F.