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CHEM3412
Synthesis of a Porphyrin

Porphyrins are hetereonuclear, macrocyclic compounds that play an important role in living organisms. Examples include the non-protein heme portion of hemoglobin in animals whereby the lone pairs on nitrogen can bind to the oxygen-carrying iron. In plants, chlorophyll uses the vast conjugation to allow absorption of light for photosynthesis. The characteristic colors of porphyrins is also due to the conjugation.

An examination of the porphyrin structure reveals that individual pyrrole units comprise the overall structure. As an aromatic compound, pyrrole can participate in electrophilic aromatic substitution reactions to form the porphyrin (your report should discuss the mechanism in great detail, including the regiochemistry). The initial porphyrinogen product is not fully aromatic, but oxidation from atmospheric oxygen in the presence of the Lewis acid silica gel allows formation of the fully conjugated porphyrin product. Using......

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