Rules of the Day 2-23-07

1st Mechanism Sheet for Today's Lecture

2nd Mechanism Sheet for Today's Lecture

1. Grignard reagents add to CO2 to give carboxylic acids (Mechanism A).

2. Carboxylic acids are reduced by LiAlH4 but not H2/Pd or NaBH4. These differences allow you to pick which functional groups in a molecule you want to reduce.

3. Fischer esterification converts a carboxylic acid into an ester using an alcohol and acid catalysis. The mechanism involves Mechanism D followed by loss of an H2O via protonation.

4. Carboxylic acids react with SOCl2 to give acid chlorides via a chlorosulfite intermediate that then reacts according to Mechanism B to give the acid chloride. This is a very valuable reaction because acid chlorides can be easily converted into other carboxylic acid derivatives.

5. b-keto acids and b-dicarboxylic acids can be decarboxylated via a six-membered ring transition state facilitated by a hydrogen bond and six-membered ring conformation that means they are "poised" to react.

Homework: Begin Working on Homework Problem Set 5. It will be due before class next Wednesday, February 28. Reading: Sections 17.4-17.9 Problems in Book: 17.1-17.8, 17.19, 17.22, 17.26, 17.32, 17.35 You will not turn these in but they are very helpful to PREPARE for the next lecture.