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50., , => Molecular mass is double of the empirical formula mass., Molecular Formula is CH,, , Step il, é 2H,, “H,, 4» 2-methylpentane, a, , CH, Structure of 2-methylpentaneis _, >CH—CH,—CH.—CH,, , Hence, the molecule has a five carbon chain with a methyl group at the, second carbon atom,, , °A adds a molecule of H,0 in the presence of Hg™ and Hit should be an, alkyne. Two possible structures for ‘A’ are, , CHT cH,, cue once, or cn cH-Ch.-cach, 1 u, Since the ketone (B} gives a positive iodoform test, it should contain a, —COCH, group. Hence the structure of ketone is as follows :, cH,, cH cH—CH—Co—cH,, Therefore structure of alkyne is Il, Two molecules of hydrogen add on ‘A’ this shows that ‘A’ is either an, alkadiene or an alkyne,, (On reductive Gzonolysis ‘A’ gives three fragments, one of which 1s, , dialdehyde, Hence, the molecule has broken down at two sites, Therefore,, “A’has two double bonds. It gives the following three fragments :, , OHC—CH,—CH,—CHO. CH,CHO and CH—CO—CH,, Hence, its structure as deduced from the three fragments must be, , (CH,—CH=CH —CH,—CH,—CH=C — CH,, Hy, a), Reactions, (ay_ome_, oi-c4 J Suen ono4 Cec bail, 5 Lol oud, , cH,, BUS CH. CHO + OHC—CH,—CH,—CHO + 0=0< cn, , r