Question

for the reaction: acetaminophen + (NaOH/EtOH note: etoh is ethanol) and butyl iodide ---------------> 4-butoxyacetanilide

a) 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?

b) 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.

c) 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

Answer 1

The Reactiom NH COCH3 NHCOCHS NaoH/etoH HI OHi ос,На OCH Acelamimophen 4-butoxyacetanilide エH is an example f Williamson ester Synthesis as The PuT pose of wsing the NaoHetoH olutiE to Temore the prolon from -oH gTOup, participate fm Sn2 reaction Can NHCOCH3 NHCOCH3 NabH Eto H OH If this step does ot Occur the SN2 Teaction occur due to unavailability of enough won't -OH Toup the nucleophilicity in Upon completion of the reactn , addition remove the added to NaoHEtoH wan the System and to drive th forward reaction NaI H0 NaoH HI Scanned with CamScanner

possible side reactiom The NaoH Eto Et OH Eto Et O C Hg butyl ethyl ether hilinc iasapeghog CS Scanned, with CamScanner