Problems Set Meeting 9 (February 9)

1. Referring to the conversion of 2,6-dimethylnitrobenzene to to 2,6-dimethylaniline, answer the following questions.

a. Why is concentrated hydrochloric acid needed in the first part of the reaction?

b. What is the function of the glacial acid acid in the reaction?

c. What is the function of the potassium hydroxide solution?

d. What is potassium carbonate used for in this reaction?

2. Diethyl ether is distilled off using the setup shown on page 51 of the reader. Answer the following questions:

a. At which points should the setup be clamped?

b. What is used as a heat source for the distillation?

c. Why is it important to have a good seal at the connection between the three-way distilling head and the water jacketed condenser?

d. During the distillation, water is circulated through the water jacketed condenser. Which part of the condenser is connected to the water hose coming from the tap?

e. Why is a distillation used in this step?

3. Referring to the conversion of 2,6-dimethylaniline to a-Chloro-2,6-dimethylacetanilide , answer the following questions.

a. Why are anhydrous conditions necessary in this step? Show pertinent equations.

b. What changes in the IR spectrum of the product compared to the starting material?

c. Why is it important that the product is dry for the next step?