Problems Set Meeting 9

The next quiz will be administered on May 5, 2005 at 11 am and will cover the entire Lidocaine project.

The final paper will be due on May 13, 2005 at 5 pm in YH1217.

You should try to finish step 1 and step two on the first day of the project.

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

a. Three equivalents of stannous chloride are used in the first part of the reaction. Explain briefly and show pertinent chemical equations.

b. Why is it important to adjust the pH-value properly in this reaction?

c. Why is it not advisable to wash the precipitate of the first step of the reaction with water?

d. What is the function of the potassium hydroxide in the second part of the reaction? Show pertinent chemical equations.

e. Where should the setup be clamped during the distillation? Explain briefly why.

f. How do yo prepare the GC sample for the product?

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

a. What is the solvent in this reaction? Why is it chosen?

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

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