Section-D: Comprehension Type
Comprehension (Alkyl Halides-2)
An organic compound A has molecular formula C8H13Cl and it can be resolved into enantiomers as well as diastereomers. Reducing A using NaBH4 yeields a hydrocarbon b, which is still resolvable into enantiomers but can’t be resolved into diastereomers. A on refluxing with ethanolic solution of C2H5OK yields C which can’t be resolved into enantiomers. C on catalytic hydrogenation with H2/Pt yields a hydrocarbon “C8H16” which on chlorination in UV-light produced four monochloro derivatives D, E, F and G, which are all constitutional isomers having molecular formula “C8H15Cl”. Amongst the above monochloro derivatives, D is reluctant to bimolecular elimination reaction(E2) on treatment with ethanolic solution of C2H5OK while G on similar treatment reproduced B as the single possible elimination product. Treatment of E with ethanolic solution of C2H5OK produced H, an isomer of B as the single possible elimination product, while F on similar treatment produced a mixture of B and H where H is the major product.
Which of the following will give-off maximum heat on catalytic hydrogenation?