Chapter 15: Q22P (page 477)
Draw and name all possible aromatic compounds with the formula C8H9Br.
Short Answer
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Chapter 15: Q22P (page 477)
Draw and name all possible aromatic compounds with the formula C8H9Br.
Answer




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1-Phenyl-2-butene has an ultraviolet absorption (). On treatment with a small amount of strong acid, isomerization occurs and a new substance with () is formed. Propose a structure for this isomer, and suggest a mechanism for its formation.
Draw an energy diagram for the three molecular orbitals of the cyclopropenyl system(C3H3). How are these three molecular orbitals occupied in the cyclopropenyl anion, cation, and radical? Which of the three substances is aromatic according to Hückel’s rule?
To be aromatic, a molecule must have 4n+2 p electrons and must have a planar, monocyclic system of conjugation. Cyclodecapentaene fulfills one of these criteria but not the other and has resisted all attempts at synthesis. Explain.

7 Propose structures for aromatic compounds that have the following NMR spectra:
(a)

b)

c)

Look at the five resonance structures for phenanthrene (Problem 15-26), and predict which of its carbon-carbon bonds is the shortest.
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