Problem set 6.pdf

Name:………………………
Chemistry 1310/2370 - Synthetic Organic Chemistry
Problem Set 6: Due Date 12/05/08 – 3:00 PM
A. Provide specific examples for starting materials, products, and pertinent reaction conditions for
the following name reactions.
1. Sonogashira coupling
2. Edman degradation
3. Bergman reaction
4. Hofmann elimination

B. Provide a complete and detailed retrosynthesis of 1,2-diphenylethanol. You will have to clearly
differentiate between synthons and reagents to get full credit. Your starting materials shall not
have more than 6 carbon atoms.

C. Provide a detailed mechanism (with correct arrow pushing!) of an ozonolysis reaction.
BONUS: what is the reducing agent used for in the workup?

D. Add all missing reagents and important reaction conditions into the following reaction
sequence.
OTf
H H O
H
O
SiMe 3
H H
H
H O