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Experiment 3: Alkylation of Acetaminophen

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Page 2 of 6

The first step in this reaction is to reflux acetaminophen in a NaOH/EtOH solution, followed by the addition of butyl iodide. What is the purpose of using the NaOH/EtOH solution? Would the S N2 reaction still occur if the first step was not completed? Why or why not? [2 Marks]

Upon completion of the reaction (before filtration), an additional 4.0 mL of 1.0 M NaOH/EtOH was added to the reaction. What was the purpose of this step? Include a chemical reaction as part of your answer. [2 Marks]

The term “side reactions” refers to any chemical reaction that can occur that form products other than the desired product. Side reactions can consume the reactants of your intended reaction, and can affect the percent yield of your target product. One possible side reaction produces butyl ethyl ether. Draw the complete reaction mechanism for the formation of butyl ethyl ether as a side product [2 Marks]...