lab report Electrophilic Aromatic Substitution

lab report Electrophilic Aromatic Substitution -...

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Electrophilic Aromatic Substitution: Iodination of Salicylamide Mechanism: Iodination of Salicylamide (meta attack): Iodination of Salicylamide (para attack): Procedures: Procedures in lab manual should be sufficient. Data Table: Reactants MW Amount Used Mol Mol Equivalent Salicylamide 137.14 g 1.029 g .00750 mol 1 Sodium Iodide 149.9 g 1.20 g .00801 mol 1 Products MW Amount Obtained % Yield Crude 263.03 g/mol 2.405 g 122% Recrystallized Crude 263.03 g/mol .009 g .4% (%recovery) Results and Discussions: Iodination is an example of electrophilic aromatic substitution. The purpose of this experiment was to demonstrate the regiochemistry of electrophilic aromatic substitutions for the iodination of salicylamide. In other words, observe substitution patterns when reacting salicylamide with ethanol, sodium iodide, and sodium hypochlorite. Although salicylamide is used to make analgesic, antipyretic, antirheumatic drugs and other pharmaceutical products, we used it as a reactant to produce iodosalicylamide. Salicylamide has two functional groups substituted on two adjacent carbons of a 6 carbon benzene ring; a hydroxyl and an amide group. To accurately design an experiment involving an electrophilic substitution reaction performed on salicylamide, several factors
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must be considered. One factor is the relative rate of the reaction. The substituent group that decreases the reaction rate relative to the reaction rate of salicylamide is called the deactivator. Deactivators withdraw electrons and decrease the electron density of the aromatic ring. The amide group attached to salicylamide is a meta directing electron- withdrawing group that
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