1. Kagan Ether Lab
Chemistry 2140
March 10, 2017

2. Structure Reactivity Mechanism Synthesis Analysis
The Pillars of Chemistry
Structure
Reactivity
Mechanism
Synthesis
Analysis

3. Kagan’s Ether

4. Cool Stuff

5. The Lab: First Step
1. Charge a dry round bottom flask with 2-bromobenzaldehyde (5.0 g, 27.0 mmol,1 equiv.), CuI (0.103 g, 0.54 mmol, 0.02 equiv.) and Pd(PPh3)4 (3.13 g, 2.7 mmol, 0.1 equiv).
2. Subject the above mixture to three purge cycles of vacuum and argon gas.
3. Add 30 mL of Et3N and phenyl acetylene (5.52 g, 54.0 mmol, 2 equiv) to the reaction mixture.
4. Allow the reaction mixture to stir at 60 °C for 2 hours.
5. Dilute the reaction mixture with ether and water.
6. Extract the aqueous phase three times with ether.
7. Dry the concentrated organic phases over Na2SO4 and concentrate in vacuum.
8. Purify the crude product (pure pentane) by flash column chromatography to obtain the product.

6. Sonogashira Coupling: Mechanism

7. Your Product
You don’t want this-
Glaser coupling product!

8. Glaser Coupling Mechanism
Confused?
Good, you should be.

9. The Lab: Second Step

10. Research, Life…Whatever

11. The Mechanism

12. Why I Want This!

13. Could We Do This?

14. Enantioselective Synthesis Asymmetric Organocatalysis!

15. Show the 3D Structure!

16. Research times lie ahead. Soon, you will all have to choose
between what is right, and what is easy.