Yield given. Multistep reaction. Yields of byproduct given;

1: 88 percent / bis(trimethylsilyl)cyclohexadiene, iodine / CHCl3 / 0.08 h / Ambient temperature 3: 85 percent / sodium acetate, H2 / Pd/C / methanol; benzene / 40 °C 4: 67 percent / 10 percent ammonium cer(IV) nitrate (aq.) / acetonitrile 5: 84 percent / conc. H2SO4 View Scheme

bis(trimethylsilyl)cyclohexadiene; iodine in methanol 0.0333333 h;

bis(trimethylsilyl)cyclohexadiene; iodine in chloroform 0.0833333 h; Ambient temperature;

1: 88 percent / bis(trimethylsilyl)cyclohexadiene, iodine / CHCl3 / 0.08 h / Ambient temperature View Scheme