Question

Treatment of the bicyclic chloride A with lithium in tetrahydrofuran (THF) gave the monocyclic product B, CoH9Li. In deuterated THF, B exhibited a single proton NMR signal at 6.72 ppm and a single 13C-NMR signal at about 110 ppm. Treatment of B with tetraethylammonium chloride gave a white solid in which N(C2H5)4 replaces Li. Draw a structure for the lithium derivative B. Cl Draw cations and anions in separate sketchers. Separate structures with +signs from the drop-down menu.Treatment of cycloheptatriene with one equivalent of bromine gave an oily dibromide that on heating in vacuum at 70° left tropylium bromide, C,H7Br, as yellow crystals, melting point 198-200°. Tropylium bromide is an unusual organic bromide, intrinsically colored and soluble in water but not in non-polar organic solvents like hexane. Draw the structure of tropylium bromide НН 1 eq. Br2 70°C at 1mm C7HBr A, yellow crystals HBr oily dibromide cycloheptatriene Draw cations and anions in separate sketchers. Separate structures with+ signs from the drop-down menu.

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