Packet 9: Tossup 16

A reaction that produces this compound creates undesired side products if the intermediate reacts with phenyl·diazo·methane or an alcohol. TTIP reacts with a Grignard reagent to generate a hydroxylated version of this compound in the Kulinkovich reaction. Halogenated derivatives of this compound are converted into allenes by an organolithium base in the Skattebøl rearrangement. A carbanion displaces bromine in the last step of the Bingel reaction used to add this compound to fullerenes. The Coulson–Moffitt and Walsh models describe the intermolecular bonding of this compound, which was first synthesized by reacting sodium with an alkyl halide. A carbenoid intermediate formed from zinc and di·iodomethane reacts with an alkene (10[1])to form this compound in the Simmons–Smith reaction. For 10 points, name this simplest cyclic hydrocarbon. ■END■

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