Explain why triphenylene resembles benzene in that it does not undergo addition

Chapter 17, Problem 17.65

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Explain why triphenylene resembles benzene in that it does not undergo addition reactions with Br2, but phenanthrene reacts with Br2 to yield the addition product drawn. (Hint: Draw resonance structures for both triphenylene and phenanthrene, and use them to determine how delocalized each bond is.) Br Br Br2 triphenylene phenanthrene

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