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CHM 2220 Organic Chemistry 2 Winter Term 2007 Problem Set #1 of 5 Answer Key 20 PTS Instructor: Prof. Andreana
 

Summary: CHM 2220 Organic Chemistry 2 Winter Term 2007
Problem Set #1 of 5 Answer Key 20 PTS Instructor: Prof. Andreana
Room #: DRY 0146
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1) Draw the mechanism for the following reaction. 4 PTS
Cl
O
NCO1) NaN3
2)
Answer:
The acyl chloride is a potent electrophile and N3
-
is a nucleophile, so the first part of the reaction
involves addition-elimination to make the acyl azide. Upon heating, the Ph-CO bond breaks and a
Ph-N bond forms. This suggests a 1,2-shift, promoted by loss of N2.
2) Draw the mechanism for the following reaction. 4 PTS
H3C

  

Source: Andreana, Peter R. - Department of Chemistry, Wayne State University

 

Collections: Chemistry