CHEM 212 Lecture Notes - Lecture 7: Electrophilic Aromatic Substitution, Aromaticity, Halogenation

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Solomons and fryhle chapter 8, 15 (alkenes & alkynes ii, reactions of aromatic compounds) Techniques: weights and measures, recrystallization, filtration, melting point. In this experiment, we will compare and contrast the bromination of an alkene and the bromination of an aromatic compound. In each case, our active brominating agent will be elemental bromine; however, the method in which we generate this bromine will be different. In the first experiment, we will use a solid source of bromine, pyridinium tribromide, and in the second experiment, we will generate bromine by the oxidation of sodium bromide with hyphochlorite. Traditionally, bromination reactions would take place using elemental bromine, in a halogenated solvent such as chloroform or dichloromethane. However, handling liquid bromine is a safety concern, as it is highly toxic and volatile, and halogenated solvents pose a serious waste management problem. In this lab, we will use solid sources of bromine that are easy to handle and we will generate more benign waste.