LabReport2 - Sierra Burden 10/15/10 Tim Blake Synthesis of...

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Sierra Burden 10/15/10 Tim Blake Synthesis of Acetanilide The reaction reagents are aniline and acetic anhydride. Due to the electronegativity differences between carbon and oxygen, carbon has a partial positive charge and the oxygen has a partial negative charge. The carbon, therefore, is an electrophilic center and the lone pair on the amino-benzene attacks the acetic anhydride. As a result, the carbon-oxygen double bond is eliminated, nitrogen gains a a positive charge, and oxygen gains a negative charge. The OCOCH3 can stabilize charge with resonance, so it leaves the compound. The lone pair on oxygen forms a double bond with carbon, which gets rid of oxygen and carbon's charge. The OCOCH3- deprotonates the nitrogen and becomes acetic acid. The nitrogen no longer carries its positive charge and the product of the reaction is acetanilide. The addition of charcoal should have removed the colored impurities from the solution of aniline, water and anhydride. Before adding the charcoal, however, there were not
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This note was uploaded on 09/19/2011 for the course BIOLOGY 44Y taught by Professor Smith during the Winter '11 term at Stanford.

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LabReport2 - Sierra Burden 10/15/10 Tim Blake Synthesis of...

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