Problems Set Meeting 9

The next quiz will be administered on February 8, 2005 at 12 pm and will cover the entire Lidocaine project.

The final paper will be due on February 11, 2005 at 5 pm in YH1217.

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

a. Why is it important to use concentrated hydrochloric acid in the first part of the reaction? Show pertinent chemical equations.

b. How many equivalents of stannous chloride are used in the reaction?

c. What is the function of the potassium hydroxide in this reaction? Show pertinent chemical equations.

d. At which points should the setup be clamped during the distillation? Explain briefly why.

e. Why is it important to use a vacuum adapter in the setup?

f. What are the characteristic changes in the IR spectrum going from 2,6-dimethylnitrobenzene to 2,6-dimethylaniline (include functional groups and wavenumbers)?

2. 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 chemical equations.

b. What is used as solvent in this reaction?

c. Why should reagent bottle for the a-chloroacetyl chloride be kept close?