Rules of the Day 3-19-07

Click here for today's lecture mechanism sheet 1

Click here for today's lecture mechanism sheet 2

1. Amides react with LiAlH4 to give amines. The mechanism is Mechanism B in which the -OAlH3 leaves!!! followed by H- attack of a C=N bond. Remember to think of LiAlH4 as a nucleophilic H- attached to the Lewis acid AlH3.

2. There are four new concepts associated with chapter 19. Click on these one at a time to get more information.

A) Reactions favor the formation of weaker bases at equilibrium (provides a motive), so you need to have a Table of pKa values

B) Enolates as nucleophiles

C) Beta-Dicarbonyl species are especially acidic

D) Conjugate addition to alpha,beta unsaturated carbonyl species.

3. Enolates are resonance stabilized. By far the most important reactions of enolates are with carbonyl groups to make carbon-carbon bonds.

4. Alpha carbons are next to the carbonyl group, beta carbons are next to alpha carbons. 

Homework: Continue working on Homework Problem Set 7. It will be due before class on Wednesday, March 21. Reading: Sections 19.3 Problems in Book: 19.4-19.6, 19.20, 19.21, 19.28, 19.29, 19.30 You will not turn these in but they are very helpful to PREPARE for the next lecture.