216 W11-Expt 1notes - Chem 216 W11 Notes Topic: _Experiment...

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Chem 216 W11 Notes Topic : __Experiment 1____ page 1 of 2. Experiment 1: Synthesis of Acetamides from Aniline and Substituted Anilines Many of the acetylated [CH 3 –C(=O)-] derivatives of aromatic amines (aka anilines) and phenols are pharmacologically important compounds. Some of these exhibit distinct analgesic activity. Two of the most representative examples are: H N CH 3 O acetaminophen ( Tylenol) HO O CH 3 O O HO acetylsalicylic acid ( Aspirin) ======================================================================= The reaction to be carried out in this experiment is: Acetylation of aniline H N H aniline (nucleophile) CH 3 O O O H 3 C δ - δ + acetic anhydride (electrophile) H N CH 3 O acetanilide CH 3 HO O + acetic acid Both aniline and acetic anhydride are somewhat viscous liquids. So, simply mixing them together does not result in the efficient formation of acetanilide. Therefore, a solvent (in this case water) is used to dissolve and evenly disperse two reactants in it. R'
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This note was uploaded on 03/19/2011 for the course CHEMISTRY 216 taught by Professor Schultz during the Spring '11 term at University of Michigan.

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216 W11-Expt 1notes - Chem 216 W11 Notes Topic: _Experiment...

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