Problems Set (Meeting 9)

Announcements

1. The next quiz will be administered on Thursday February 9, 2006 at 12 am and will cover most likely the entire Lidocaine project.

2. The final paper will be due on Friday February 17, 2006 at 5 pm in YH3077E.

3. You should try to finish the first two steps on the first day of the project.

1. Referring to the conversion of 2,6-dimethylnitrobenzene to 2,6-dimethylaniline (step 1), answer the following questions. Explain briefly and show pertinent chemical equations.

a. Which reducing reagent is used in this part of the reaction? Rationalize this choice. What could be used alternatively?

b. The reaction has to carried out in a strongly acidic medium. How is this accomplished?

c. A student "rinses" the white solid obtain after the first reaction with water. What would he observe?

d. Which drying agent is used in this step? Rationalize this choice.

e. For the distillation, the procedure asks to use a vacuum adapter. Why?

f. Where is the water supply attached on the water jacketed condenser when using it for the distillation?

2. Referring to the conversion of 2,6-dimethylaniline to a-Chloro-2,6-dimethylacetanilide (step 2), answer the following questions. Explain briefly and show pertinent

a. a-Chloroacetyl chloride is used in this step. Rationalize this choice.

b. What is used a solvent in this reaction?

c. Why is it important that the compound is dry?