Problem 4- Edman Degradation H N N H S O O CH3 HCl, H2O, Heat S N NH CH3

H N HN

HO S OH CH3 N NH S CH3

H N

S HN N H

CH3 OH OH H OH OH N CH3 N S H

H3C HO H2O

NH N S

S OH2 OH HN CH3 H

1. Add curved arrows to the reaction above to show the mechanism of the reaction. Use H2O and HCl as needed. 2. Draw four resonance structures of the starting material. All atoms should have full octets in all structures. H N N H

O CH3

3. Identify the most acidic proton in the starting material and the product. Also, identify the most basic atom in each. Explain your answer. H N N H S O O CH3 N S NH CH3

Created by Hanna Key Grinnell College