Criteria for Aromaticity 1. The system must be cyclic 2. The system must be planar (flat) 3. Each ring atom must be part of a completely extended pi system.

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Presentation transcript:

Criteria for Aromaticity 1. The system must be cyclic 2. The system must be planar (flat) 3. Each ring atom must be part of a completely extended pi system 4. The completely extended pi system must contain the Hückel # of pi electrons (4n+2)

Examples of Hückel 4n+2 Systems 4n+2 = # of pi electrons such that n = 0,1,2,3,4,5, etc. 4n+2 = # of pi electrons such that n = 0,1,2,3,4,5, etc.

Basis for Electrophilic Aromatic Substitution Electrophile attack on electron-rich aromatic ring Electrophile attack on electron-rich aromatic ring Temporary loss of aromatic character Temporary loss of aromatic character Loss of proton to restore aromaticity Loss of proton to restore aromaticity

Electrophilic Aromatic Substitution Nitration Nitration Halogenation Halogenation Friedel-Crafts Alkylation Friedel-Crafts Alkylation Friedel-Crafts Acylation Friedel-Crafts Acylation Sulfonation Sulfonation