Problem

(a) Draw all the Kekulé structures of anthracene and phenanthrene. (b) Propos...

(a) Draw all the Kekulé structures of anthracene and phenanthrene.

(b) Propose mechanisms for the two additions shown.

(c) In Chapter 8, most of the additions of bromine to double bonds gave entirely anti stereochemistry. Explain why the addition to phenanthrene gives a mixture of syn and anti stereochemistry.

(d) When the product from (c) is heated, HBr is evolved and 9-bromophenanthrene results. Propose a mechanism for this dehydrohalogenation.

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