Rules of the Day 3-5-08

Click here for a copy of the mechanism sheet used in lecture today.

1. It is best to hydrolyze esters in base and amides in acid, although either will hydrolyze in acid or base.

2. Acid chlorides, anhydrides, and esters react with amines involving an initial attack to create a zwitterionic tetrahedral intermediate, followed by a proton transfer, followed by loss of the leaving group to give the amide.

3. You can make any of the less reactive carboxylic acid derivatives from any of the more reactive ones using the proper nucleophile, but NOT vice versa. You can hydrolyze all of the carboxylic acid derivatives to give carboxylic acids, that can be converted to acid chlorides. The combination provides a way to interconvert all the derivatives.

4. The KRE for carboxylic acid derivatives are the carbonyl attached to a Cl atom, a O-C(O)-R group, an OR' group, or a N(R')2 group. For synthesis, the bond to be made is the bond that connects these groups to the carbonyl.

5. The key to complex organic synthesis is being able to recognize the relevant functional groups in a complex molecule, then knowing how to make the appropriate new bonds.

Homework: Start Working on Homework Problem Set 7. It will be due before class on Wednesday, March 19. Reading: Sections 18.7-18.10 Problems in Book: 18.8-18.11, 18.34 You will not turn these in but they are very helpful to PREPARE for the next lecture.