SYNTHESIS OF LIDOCAINE. Part C. PREPARATION OF LIDOCAINE

Experimental Organic Chemistry: A Miniscale and Microscale Approach
Section 21.4
SYNTHESIS OF LIDOCAINE. Part C. PREPARATION OF LIDOCAINE
NAME (print):
DATE:
INSTRUCTOR:
LABORATORY SECTION:
1. Mechanistically, the reaction to be performed (underline all answers that apply) is (a) an elimination reaction,
(b) a nucleophilic substitution reaction, (c) a nucleophilic addition-elimination reaction, (d) an electrophilic
substitution reaction, (e) a free-radical substitution reaction, (f) an oxidation of the organic substrate, (g) a
reduction of the organic substrate, (h) none of these.
2. What is the limiting reactant in this reaction? Show your work.
3. Which reactant is used in excess? Explain why it is used in excess.
4. Explain why it is important to dry the glassware prior to reacting diethylamine with 37.
5. Explain how unchanged 37 is removed from 25 in the workup procedure used.
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©2006 Thomson Brooks/Cole

Experimental Organic Chemistry: A Miniscale and Microscale Approach
6. Why is it necessary to basify the aqueous solution prior to extracting the lidocaine with diethyl ether?
7. Why is acetone added to the aqueous solution of lidocaine bisulfate?
8. Why does scratching at the air-liquid interface with a glass rod help to induce crystallization?
9. List the possible effects of getting diethylamine in your eyes.
10. List the possible effects of inhaling excessive amounts of diethylamine.
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©2006 Thomson Brooks/Cole