Tossup

Early attempts to synthesize this molecule with hydroiodic acid at high temperatures failed due to a methyl shift discovered by Markovnikov, Kishner, and Zelinsky. Mixtures of this molecule and methanol form a binary liquid that displays critical opalescence. Sebacoyl chloride is dissolved in this compound and forms a thin, pullable fiber when reacted with hexa·methyl·ene·di·amine (-5[2])in water (-5[2])in the nylon (-5[1])rope trick experiment. (-5[1])This molecule is produced when a precursor whose NMR (-5[1])spectrum consists of a single peak at 7.3 ppm is hydrogenated with Raney nickel. (-5[3])The added steric bulk created (10[1])from adding a substituent (-5[1])to this molecule can be quantified with A-values. (10[2])The (-5[1])sterics (10[1])between (10[1])this (10[1])molecule’s flagpole hydrogens (10[1]-5[1])make its boat conformation (10[1])less (-5[1])stable (10[1])than its chair conformation. (10[1])For 10 points, (10[1])name this cyclic alkane with formula C6H12. ■END■ (10[9]0[4])

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