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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 ZnH2O produced two molecules of ethanol. Identify A to F.

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Solution

2-Bromopentane and 1-Bromopentane (B and C).After ozonolysis of A it produced aldehyde D. On treatment of NaBH4 on D it produced primary alcohol, which undergoes reaction with sulphuric acid to formed alkene.
1043796_237994_ans_578739b5ffad4b9f9b65eea3d3d13201.PNG

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