Chem 351 Lectures - Spring 2006

No

Date

Topics

Chapter in Smith

Lecture Notes

1

1/13 Bp and mp of cis vs trans alkenes. Triacylglycerols  or Fats. 10.4, 10.6, 26.3

2

1/18 Alkene preparation. Double bond addition reactions.  10.7-10.11  

3

1/20 Hydrohalogenation mechanism. Hydration. 10.9-10.12

4

1/23 Hydration showing R+ rearrangement. Halogenation stereochemistry and mechanism. 10.12-10.15

5

1/25 Halohydrin formation. Hydroboration. 10

6

1/27 Hydroboration using 9-BBN. Synthesis. 10

7

1/30 Alkyne acidity. Acetylide ions as nucleophiles. HX addition. 11

8

2/1 Alkyne Hydration. 11

9

2/3 Alkyne hydroboration and halogenation. Redox reactions. Catalytic Hydrogenation. 11, 12

10

2/6 Alkyne reduction. Oxidation of alkenes with peroxyacids. 12
rev 1 2/7 Rxns Review 10-12 p1, p2

11

2/8 Hydride reducing agents. Oxidation of alkenes to diols. 12

 

2/10 Exam 1   Version A : Version B : Version C

12

2/13 Ozonolysis of alkenes and alkynes. Oxidation of alcohols. 12

 

2/15 No Class - Assessment Day    

13

2/17 Radicals. Halogenation of Alkanes. 13

14

2/20 Radical bromination vs chlorination. Allylic bromination with NBS. 13

15

2/22 Lipid peroxidation and antioxidants. Peroxide effect on HBr addition. 13

16

2/24 Dienes. Resonance theory. 1,2 vs 1,4 Addition. 16

17

2/27 Stability of conjugated dienes. Diels-Alder cycloaddition. 16

18

3/1 Electron demand in Diels-Alder rxns. The endo rule. 16

19

3/3 Benzene. Aromaticity. 17

movie

20

3/6 MO Theory and Huckels Rule. 17

21

3/8 More Aromatics. 17

 

3/10 Exam 2   answers

22

3/20 Electrophilic aromatic substitution (EAS). 18

23

3/22 Substituent effects in EAS. 18

24

3/24 Disubstituted benzenes in EAS reactions. Reactions on aromatic side chains. 18

25

3/27 Retake Exam 2    
lab 3/29 Limitations of Friedel-Crafts reactions. 18

26

3/29 Carboxylic acids. 19

27

3/31 Reduction of carbonyl compounds 20

28

4/3 Organometallic Compounds - The Grignard Reagent 20
29 4/5 Organometallic Compounds - Organocuprates 20

 

4/7 Exam 3 18-20 answers

30

4/10 Naming of Aldehydes and Ketones. Addition oh HCN and the Wittig Reaction. 21

31

4/12 Addition of amines and alcohols to aldehydes and ketones. 21

32

4/17 Carboxylic acid derivatives naming and reactions. 22

33

4/19 Interconversion of carboxylic acid derivatives. 22
34 4/21 Mechanism of Nitrile Hydrolysis. Enolate ions as nucleophiles:  alpha halogenation. 22, 23
35 4/24 Enolate ions as nucleophiles: alkylation and addition to aldehydes and ketones. 24
36 4/26 Enolate ions as nucleophiles: acyl substitution (Boom Boom) 24
  4/28 Exam 4 21-24  
5/1

Final Exam