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16. Electrophilic Aromatic Substitution

Experiment 16 Electrophilic Aromatic Substitution Page 1 of 8 16. Electrophilic Aromatic Substitution A. Introduction Aromatic compounds are especially stable and despite having p-bonds do not react like typical alkenes. For example, the p-bond in 1-hexene undergoes bromination to give 1,2-dibromohexane, while benzene does not react under similar conditions (figure 1). Figure 1. Bromination of Alkenes Aromatic compounds are extremely important for their industrial and pharmaceutical use. A few prescription drugs containing one or more Aromatic rings are shown in figure 2.

Nitration of an Acetanilide Nitration of a Methyl Benzoate NH2 E "ortho attack" NH2 E NH2 E NH2 E NH2 E Additional resonance structure where all atoms have an octet. This helps to stabilize the ortho pathway. Experiment 16 – Electrophilic Aromatic Substitution Page 6 of 8 Figure 11. Meta Addition of an Electrophile to an Activated Aromatic Ring

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