Problems Set (Meeting 9)

Announcements

The next lecture (10/26/2005) will take place in YH4336.

The next quiz will be administered on Wednesday, November 2, 2005 at 12 am and will cover most likely the entire Lidocaine project.

The final paper will be due on November 10, 2005 at 5 pm in YH1217.

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?

b. The reaction has to carried out in a strongly acidic medium. Why?

c. What solvent is used in the reaction?

d. What is the function of the potassium hydroxide in the second part of the reaction?

e. Why is it important to use a vacuum adapter during the distillation?

f. Where the water supply attached on the water jacketed condenser?

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. Why a-chloroacetyl chloride used in this reaction instead of a-chloroacetic acid?

b. Why is sodium acetate added in the reaction?

c. Why is it important to keep the a-chloroacetyl chloride bottle closed as much as possible?

d. The C=O stretching frequency in the amide is relatively low. How can this observation be explained?