heterocycles - Cyclic and heterocyclic aromatic compounds...

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Unformatted text preview: Cyclic and heterocyclic aromatic compounds Chapter 14 Outline 1. Polycyclic aromatic hydrocarbons 2. Basicity and acidity of the nitrogen heterocycles 3. Chemistry of pyrrole, furan, and thiophene 4. Chemistry of pyridine Outline 1. Polycyclic aromatic hydrocarbons 2. Basicity and acidity of the nitrogen heterocycles 3. Chemistry of pyrrole, furan, and thiophene 4. Chemistry of pyridine E + CH + H E CH + H E CH + H E preferred reaction path only resonance structures without breaking aromaticity are considered -position -position NO 2 95% HNO 3 H 2 SO 4 Orientation of the electrophilic substitution on the example of naphthalene naphthalene anthracene phenanthrene pyrene When the reaction system is close to the equilibrium, substitution is directed to the more stable -position SO 3 H SO 3 H H 2 SO 4 40 o C 160 o C 85% 85% Br 75% Br 2 , CCl 4 (solven t) no catalyst Naphthalene is more reactive, than benzene Outline 1. Polycyclic aromatic hydrocarbons 2. Basicity and acidity of the nitrogen heterocycles 3. Chemistry of pyrrole, furan, and thiophene 4. Chemistry of pyridine N...
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heterocycles - Cyclic and heterocyclic aromatic compounds...

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