Chem 351 Lectures - Spring 2007

No

Date

Topics

Chapter in Smith

Lecture Notes, Powerpoints, etc.

1

1/17 E/Z designations for alkene stereoisomers. Physical properties of alkenes. 10  

2

1/19 Cis/trans isomerization. Fatty acids, retinal, hula twist. 10 Powerpoints

one bond flip     hula twist

3

1/22 Preparation of alkenes. Reactions of alkenes: HX addition. 10  

4

1/24 Reactions of alkenes: halogenation, halohydrin formation. 10 notes for lectures 1-4

5

1/26 Reactions of alkenes: hydration. 10 notes

quiz answers

6

1/29 More on Alkene Hydroboration. Intro to Alkynes. 10, 11 notes part 1

notes part 2

7

1/31 Alkyne reactions. 11 notes

8

2/2 Alkynide chemistry. Overview of redox rxns. Reduction of alkenes and alkynes. 11, 12 notes part 1

notes part 2

 

9

2/5 Mechanism of dissolving metal reduction. Reduction of alkyl halides. Epoxidation of alkenes. 12 notes

10

2/7 Dihydroxylation of alkenes. Ozonolysis. 12 notes
11 2/9 Sharpless oxidation. 12 notes

actual mechanism

 

2/12 Exam 1   answers

12

2/14 Radical reactions. Halogenation. 13 notes

13

2/16 Mechanism of halogenation. Selectivity of Br vs Cl. 13 notes

14

2/19 NBS for allylic bromination. Radical structure. Lipid peroxidation. Peroxide effect on HBr additions. 13 notes

15

2/21 Conjugation. Allylic cations and radicals. 1,2 vs 1,4 addition to conjugated dienes. 16 notes

16

2/23 Benzene. Naming of substituted benzenes. Other aromatic compounds. 17 notes

17

2/26 More on aromaticity. The basis for Huckel's rule. 17 notes

18

2/28 More on MO theory. Polycyclic aromatic hydrocarbons. 17 notes
  3/2 Exam 2    
19 3/12 Electrophilic aromatic substitution. Friedel-Crafts reactions. 18 notes

20

3/14 Other EAS reactions. Halogenation, Nitration, Sulfonation, Deuteronation.  18 notes

21

3/16 Effects of substituents in EAS reactions.  18 notes

22

3/19 EAS reactions on Disubsituted Benzenes. Other reactions of benzene ring compounds. Synthesis. 18 notes

23

3/21 Benzene diazonium chemistry. Effects of substituents in the Diels-Alder reaction. 25, 16 notes

24

3/23 Carboxylic Acids - naming and acidity. 19 notes

25

3/26 Sulfonic acids. Amino acids. Intro to Organometallic Chemistry. 19, 20 notes

26

3/28 The Grignard synthesis of alcohols. 20 notes

27

3/30 Organocuprates. Intro to Aldehydes and Ketones. 20, 21 notes
28 4/2 Nucleophilic addition to aldehydes and ketones.  21 notes
  4/4 Exam 3    

29

4/9 Acid-catalyzed addition of water and alcohols to aldehydes and ketones. Acetals. Protecting groups. 21 notes

30

4/11 Naming of carboxylic acid derivatives. 22 notes

31

4/13 Reactions and preparation of carboxylic acid derivatives. SNacyl. Thionyl chloride for acyl chloride preparation. 22 notes
32 4/16 Anhydrides as acylating agents. Hydrolysis of nitriles. 22 notes
33 4/18 Enols and enolates as nucleophiles. Bases to use for enolate formation. Halogenation. Alkylation. Kinetic vs thermodynamic enolate. 23 notes
34 4/20 Alkylation of enolates. Alkylation of enamines. Malonic ester synthesis. Aldol reaction. 23, 24 notes
35 4/23   24 notes
36 4/25   24 notes
  4/27 Exam 4 21-24  
5/2 Final Exam