Objectives Chapter 19
Brown Foote & Iverson 4th ed. Enolate Anions
Read Chapter
19.1-19.4,19.6, 19.7. Study Key reactions 1, 2, 3, 4, 7, 8,& 9 (Pg. 766-768)
1. Be able to give the structure
of the compound, which would result when an aldehyde or ketone reacted another
molecule to form an aldol condensation product. Under either basic or acidic
conditions
2. Be able to draw the
structure of the product which would result, when an aldol product were heated
to dehydration.
3. Be able to show why a
mixed aldol condensations with two different aldehydes are often undesirable
(too many combinations)
4. Be able to show how an
enolate anion can be formed when an aldehyde or ketone is reacted with lithium
diisopropylamide, LDA.
5. Show how conditions can
be controlled to produce different enolate anions: Excess LDA, and you get the
least substituted anion.(kinetics controls product formation); excess aldehyde
or ketone and you get the most highly substituted and stable enolate anion
(thermodynamics controls product formation)
6. Show how a performed
enolate anion can be used to make a directed aldol (mixed aldol) product.
7. Show how an ester, with
alpha hydrogens, can form an anion and condense with itself when reacted with
strong base (Claisen Condensation)
8. Be able to give the
mechanism of the Claisen condensation
9. Be able to show the
product which would result when a B-ketoester, (product of a Claisen
condensation), is hydrolyzed and decarboxylated (Loss of CO2)
10. Be able to do the
following problems in Chapter 19 19.1
(pg734),19.2 (pg735), 19.3 (pg 736),19.4 (pg 740), 19.10
(pg 752)19.12, (pg757) A the end of chapter 19: 18,. 19, 21, 30, 31,
33, 34, 35