Chapter 15: Q15-15-25E (page 477)
Anthracene has four resonance structures, one of which is shown. Draw the other three

Anthracene
Short Answer

Four resonance structures of anthracene
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Chapter 15: Q15-15-25E (page 477)
Anthracene has four resonance structures, one of which is shown. Draw the other three

Anthracene

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

b)

c)

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 structures corresponding to the following IUPAC names:
(a) p-Bromochlorobenzene
(b) p-Bromotoluene
(c) m-Chloroaniline
(d) 1-Chloro-3,5-dimethylbenzene
Pentalene is a most elusive molecule that has been isolated only at liquid-nitrogen temperature. The pentalene dianion, however, is well known and quite stable. Explain.
Pentalene
Pentalene dianion
All-cis cyclodecapentaene is a stable molecule that shows a single absorption in its NMR spectrum at . Tell whether it is aromatic, and explain its NMR spectrum.

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