Chapter 15: Q15-15-26E (page 477)
Phenanthrene has five resonance structures, one of which is shown. Draw the other four.
Short Answer

Five possible resonance structures of phenanthrene
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Chapter 15: Q15-15-26E (page 477)
Phenanthrene has five resonance structures, one of which is shown. Draw the other four.

Five possible resonance structures of phenanthrene
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The compound below is the product initially formed in a Claisen rearrangement (Section 18-4). This product is not isolated but tautomerizes to its enol form. Give the structure of the enol and provide an explanation as to why the enol tautomer is favored.

Draw all of the resonance forms for each. What patterns emerge?

How might you convert 1, 3, 5, 7-cyclononatetraene to an aromatic substance?
The proton NMR spectrum of a compound with formula is shown. The normal carbon-13 and DEPT experimental results are tabulated. The infrared spectrum shows peaks at 3432 and and a series of medium-sized peaks between 1618 and . Draw the structure of this compound.


Azulene, a beautiful blue hydrocarbon, is an isomer of naphthalene. Is azulene aromatic? Draw a second resonance form of azulene in addition to that shown.

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