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CHM 2220 Organic Chemistry 2220 Winter Term 2009 Problem Set #5 of 5 20 PTS Instructor: Prof. Andreana
 

Summary: CHM 2220 Organic Chemistry 2220 Winter Term 2009
Problem Set #5 of 5 20 PTS Instructor: Prof. Andreana
Room #: DRY 0146
Your Name:
Student Number:
Section Number:
Teaching Assistant's Name:
1) So far in class we have learned how to make cyclic compounds from inter- and intramolecular
processes. We have also learned of at least one ring expansion reaction, namely the Bayer-
Villager, to form lactones from cyclic ketones. Diazomethane mediated ring expansion reactions
are similar in mechanism but yet offer a carbon in place of an oxygen in the final product.
Please provide a mechanism for the following transformation and indicate what drives this
reaction forward. Make sure to account (mechanism) for the epoxide formation as well. 4 PTS
O O
O
+
CH2N2
2) Devise a synthesis of compounds A, B & C, starting from benzene. 4 PTS
OH
CN

  

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

 

Collections: Chemistry