Tossup

In the first stage of the Hock process, this molecule is alkylated with propylene to form cumene. (10[1])This compound (10[1])is the lightest (-5[1])in a mixture produced through the catalytic reforming of naphtha called BTX. A methylated derivative of this compound is nitrated three times to produce TNT. (-5[1])A different derivative (-5[1])of this compound with two methyl substituents may be (10[1])prefixed ortho-, meta-, or para- and is called xylene. Each carbon-carbon bond (10[1])in this compound has a bond order of 1.5 due to the delocalization of its (10[1])six pi electrons. (-5[1])For 10 points, a circle inside a hexagon symbolizes what aromatic compound (10[1])with the formula C6H6? ■END■ (10[2]0[1])

ANSWER: benzene [prompt on C6H6 until read] (The second line refers to toluene.)
<Murray State A, Chemistry>
= Average correct buzz position

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