Solutions_Manual_for_Organic_Chemistry_6th_Ed 358

Solutions_Manual_for_Organic_Chemistry_6th_Ed 358 - 1 6-3 1...

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Unformatted text preview: 1 6-3 1 continued (b) 6 Br Jl U c::::=> u o + Br Br Br + ( c) 6 Br ¢ Br Br 6 + flZ); a:;; + Br Br Br Cl � + Br \. a L6 Br Br � I B' + B' d ifferent positions of double bonds Y � I J + Br (ignoring enantiomers) (d) The only structure consistent with three isomers of di bromobenzene is the prism structure, called Ladenburg benzene. It also gives no test for alkenes, consi stent with the behavior of benzene. (Kekule defended his structure by claiming that the "two" structures of ortho-dibromobenzene were rapidly interconverted, equilibrating so quickly that they could never be separated. ) (e) W e n o w know that three- and four-membered ri ngs are the least stable, but this fact was unknown to chemists duri ng the mid- 1 800s when the benzene controversy was raging. Ladenburg benzene has two three-membered rings and three four-membered rings (of which only four of the rings are independent), which we would predict to be unstable. (In fact, the structure has been s ynthesized. Called p rismane, it is NOT a romatic, but rather, is very reactive toward addition reactions. ) 352 ...
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