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Naphthalene: Is It Aromatic?

Naphthalene, which contains 10 pi electrons, is aromatic according to Hückel's rule that cyclic compounds with 4n + 2 pi electrons are aromatic. The anions and cations of cyclic polyenes also show aromatic stabilization if they follow the criteria of 4n + 2 pi electrons. To draw the molecular orbital diagram of naphthalene, use a Frost circle diagram with the vertices touching the circle representing energy levels and the diameter separating bonding and antibonding orbitals. The cyclopropenyl cation is more stable than the allyl cation due to aromatic stabilization.

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85 views

Naphthalene: Is It Aromatic?

Naphthalene, which contains 10 pi electrons, is aromatic according to Hückel's rule that cyclic compounds with 4n + 2 pi electrons are aromatic. The anions and cations of cyclic polyenes also show aromatic stabilization if they follow the criteria of 4n + 2 pi electrons. To draw the molecular orbital diagram of naphthalene, use a Frost circle diagram with the vertices touching the circle representing energy levels and the diameter separating bonding and antibonding orbitals. The cyclopropenyl cation is more stable than the allyl cation due to aromatic stabilization.

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Dan Wuiyt
Copyright
© Attribution Non-Commercial (BY-NC)
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Download as PDF, TXT or read online on Scribd
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LECTURE 3

Naphthalene if n = 2 " 10 ! electrons is it aromatic? Pattern; 4n + 2 fills the degenerate pairs of bonding MO's. Also, anions and cations of cyclic polyenes show striking effects of aromatic stabilization if the same rules (criteria) for aromaticity are followed. 4n + 2 = 10 10! earomatic

use Frost circle to draw MO diagram: 4n + 2 n=0

1 2

draw polygon point down inscribe inside a circle. every place a vertice touches the circle is an energy level halfway (diameter) is separation of bonding (below) and antibonding above

"

3 4

2eRemember: C w/ 3 bonds can be planar !

C H H C H H C H H H H empty p neutral 2e- in orbital radical P orbital carbocation carbanion

cyclopropenyl cation is more stable than allyl cation due to aromaticity.

Pg. 3.1

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