Rules of the Day 3-05-07

Click here for today's lecture mechanism sheet 1

Click here for today's lecture mechanism sheet 2

Click here for today's lecture mechanism sheet 3

1. Esters require acid catalysis or base promotion to hydrolyze. Base promoted ester hydrolysis is just mechanism B followed by an acid base reaction.

2. Esters react with alcohols to give new esters in an equilibrium process catalyzed by acid.

3. Heating in in aqueous acid hydrolyzes amides in a mechanism analogous to the acid catalyzed ester hydrolysis reaction except for amides the reaction is only promoted by acid, not catalyzed by it, because the last step involves transfer of a proton to the amine group that departed.

4. Nitriles are hydrolyzed in strong acid to give carboxylic acids, a mechanism that involves formation of amides.

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

Homework: Finish Working on Homework Problem Set 6. It will be due before class next Wednesday, March 7. 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.