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143B Exam-1-spring-10-Key

143B Exam-1-spring-10-Key - Chemistry 143B Spring 2010 NAME...

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Chemistry 143B Spring, 2010 Exam #1 (4-19-10) Total Points: 100 NAME: KEY, Ima TA name: Joe Blow USE INK FOR RECORDING ANSWERS (if using pencil, no re-grades will be allowed) 1. (38 points) For the synthesis of acetanilide, the procedure directed you to first dissolve aniline in aqueous HCl (forming the salt), then add acetic anhydride followed by sodium acetate (to free base the aniline and allow it to be acylated). Let’s say the stockroom ran out of acetic anhydride but they have acetyl chloride. Since you know that this reagent will also convert amines to amides, you decide to use it. You devise a procedure in which you dissolve the aniline in methylene chloride and add the acetyl chloride. You figure that since you didn’t add HCl, there is no need to add sodium acetate. Unfortunately, you find that the reaction did not turn out as well as you had hoped. Below, write the reaction assuming that you used 2 mmol of aniline and 2 mmol of acetyl chloride. Write the structures of all of the reactants and product(s) that would form. Write the structure of the solvent above the arrow. Next, indicate the
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