Question

In this experiment we took 300 grams of acetaminophen and added 10 ml of NAOH. We did a reflux and finally added ethyl iodide to the hot solution.

3. In the synthesis of acetaminophen fromphenacetin, an ether is converted to analcohol.

a. Explain the purpose of each reaction stepin your procedure.

b.Describe the mechanism of the synthesis of phenacetin from acetaminophen.Identify the nucleophile in each step.Use curved arrows to show bonds breaking and forming.What is the leaving group?

c.Is there another nucleophile or electrophile that can react with the reagent(s) you chose that could interfere with your desired reaction?In other words, is there another atom in phenacetin that

couldreact withyour chosen reagent so acetaminophen was not produced?If so, which atom in phenacetin reacted with your reagent and what compound was produced?

d. How is the phenacetin to acetaminophen related to the sucrose hydrolysis to glucose and fructose reaction? (Hint: thinkfunctional group conversion.

Answer 1

a. Explain the purpose of each reaction step in your procedure.

b) Describe the mechanism of the synthesis of phenacetin from acetaminophen. Identify the nucleophile in each step. Use curved arrows to show bonds breaking and forming. What is the leaving group?

c) Is there another nucleophile or electrophile that can react with the reagent(s) you chose that could interfere with your desired reaction? In other words, is there another atom in phenacetin that could react with your chosen reagent so acetaminophen was not produced? If so, which atom in phenacetin reacted with your reagent and what compound was produced?

It could be:

d) How is the phenacetin to acetaminophen related to the sucrose hydrolysis to glucose and fructose reaction? (Hint: think functional group conversion)

Phenacetin can not hydrolyze sucrose because the nucleophile is inactivated by ether function, while the nucleophile is free in acetaminophen (phenol) and may be the nucleophilic attack and hydrolyze sucrose into two monomers (glucose and fructose).