Rules of the Day 3-3-08

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

1. Base promoted ester hydrolysis is just mechanism B followed by an acid base reaction.

2. It looks as thought the plot for the Star Wars movies is really derived from carbonyl chemistry.

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.

6. 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.

Homework: Continue Working on Homework Problem Set 6. It will be due before class on Wednesday, March 5. Reading: Sections No new reading Problems in Book: 18.24, 18.25, 18.27, 18.32 You will not turn these in but they are very helpful to PREPARE for the next lecture.