7. Although Huckel's rule strictly applies only to monocyclic compounds, it does appear to have application to certain bicyclic compounds, if one assumes use of resonance structures involving only the perimeter double bonds, as shown with one resonance contributor for naphthalene below. Both Naphthalene and azulene have 10 n electrons and are aromatic. Pentalene (shown below) is apparently antiaromatic and is unstable even at very low temperatures. Heptalene has been made but it adds bromine, it reacts with acids, and it is not planar. Is Huckel's rule applicable to these compounds? If so, explain their lack of aromaticity. Pentalene Heptalene

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7. Although Huckel's rule strictly applies only to monocyclic compounds, it does appear to have
application to certain bicyclic compounds, if one assumes use of resonance structures involving
only the perimeter double bonds, as shown with one resonance contributor for naphthalene
below.
Both Naphthalene and azulene have 10 t electrons and are aromatic. Pentalene (shown below)
is apparently antiaromatic and is unstable even at very low temperatures. Heptalene has been made but
it adds bromine, it reacts with acids, and it is not planar. Is Huckel's rule applicable to these compounds?
If so, explain their lack of aromaticity.
Pentalene
Heptalene
Transcribed Image Text:7. Although Huckel's rule strictly applies only to monocyclic compounds, it does appear to have application to certain bicyclic compounds, if one assumes use of resonance structures involving only the perimeter double bonds, as shown with one resonance contributor for naphthalene below. Both Naphthalene and azulene have 10 t electrons and are aromatic. Pentalene (shown below) is apparently antiaromatic and is unstable even at very low temperatures. Heptalene has been made but it adds bromine, it reacts with acids, and it is not planar. Is Huckel's rule applicable to these compounds? If so, explain their lack of aromaticity. Pentalene Heptalene
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