University12 min

Aromaticity and electrophilic aromatic substitution

Count π electrons to apply Hückel's rule, then predict where the electrophile goes: ortho/para or meta, and why.

The essentials

1

The conditions for aromaticity

A system is aromatic if it is cyclic, planar, fully conjugated (one p orbital on every ring atom) and holds 4n+24n + 2 π electrons, nn being an integer: 22, 66, 1010… With 4n4n electrons in the same geometry it is antiaromatic, hence destabilised: cyclobutadiene (44 π electrons). If planarity or conjugation is missing, it is simply non-aromatic.
2

Counting π electrons

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3

The EAS mechanism

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4

Five reactions, five electrophiles

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5

Directing effects

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