Chem 351 Tentative Lecture Schedule - Spring 2013

No

Date

Topics

 Lecture Materials

Chapter

1

 1/14 Synthesis tools. Review of reactions from Chem 350.   12

2

 1/16 Multistep synthesis. Retrosynthetic analysis.   12

3

 1/18 Alcohols and Phenols. Acidity. Methods for alcohol preparation. Hydride reductions.   13

4

 1/23 Grignard Synthesis.   13

5

 1/25 Grignard and hydride reactions with esters. SN and E Reactions of Alcohols. Protection of the OH group as an ether.   13

6

 1/28 More SN and E Reactions of Alcohols. Oxidation of Alcohols.   13

7

 1/30 Multistep Synthesis using Alcohols. Silyl ethers as protecting groups.   13

8

 2/1 Epoxides: Nomenclature, Preparation, and Reactions.   14

9

 2/4 Reactions of unsymmetrical epoxides.   14

10

 2/6 Thiols, Sulfides, Disulfides, Sulfoxides, and Sulfones.   14

11

 2/8 Crown ethers.   14
12 2/11 Dienes. Stability. Resonance vs bond hybridization arguments. Molecular orbitals of conjugated polyenes.   17
13 2/13 MO theory and pericyclic reactions. Cycloaddition and electrocyclic reactions.   17

2/15 Exam 1 .   12-14

14

 2/18 Electrocyclic reactions and sigmatropic shifts. Benzene MOs.   17

15

 2/22 Electrophilic addition to dienes. Thermodynamic vs kinetic control. Aromaticity. MO theory and the Huckel Rule. Theoretical criteria and experimental hallmarks of aromaticity.   17, 18

16

 2/25 Applying the theoretical criteria for aromaticity. The annulenes. Aromatic ions. Heteroaromatic rings.   18
17 2/27

Proton NMR of benzene ring compounds (e.g., MCPBA). Polycyclic aromatic hydrocarbons. Electrophilic aromatic substitution - general mechanism.

   19
18 3/1 Theory behind directing effects of substituents in electrophilic aromatic substitution. Synthesis of disubstituted benzenes.   19

19

 3/4 Substitution on disubstituted rings. Friedel-Crafts limitations. Synthesis strategies. Friedel-Crafts acylation followed by reduction. Sulfonation as a blocking group methodology.   19

20

 3/6

Birch reduction, Side chain reactions of benzene rings. Reduction of the nitro group.

   18, 19
21 3/8 Multistep synthesis of substituted aromatics. Nucleophilic aromatic substitution - the SNAr Mechanism.   19.13

22

 3/11

Substituent effects in Diels-Alder cycloadditions.

  17
  3/13 Other mechanisms for nucleophilic substitution on benzene rings: benzyne, diazonium, SRN1   19.14, 23.11

23

 3/15 Exam 2   17-19

24

 3/25 Aldehyde/Ketone naming and reaction types. Hydration to fomr gem-diols.   20

25

 3/27 Acetals and Thioacetals.   20

26

 4/1 Imines. Enamines.   20
27 4/3

Wittig synthesis. Naming of Carboxylic Acids. Overview of reactions of Carboxyllic Acids and Carboxylic Acid Derivatives.

   20-21
28 4/5 Reactivity of Carboxylic Acids and Carboxylic Acid Derivatives. Preparation of Acyl Chlorides using Thionyl Chloride. Interconversions of CADs. Hydrolysis of CADs.   21

29

 4/8 Reactions of nitriles.   21
30 4/10 Reactions of esters, acid chlorides, and nitriles with hydride sources and organometallics.   21
  4/12 Synthesis review. Naming of CADs.   21
31 4/15 Exam 3.    

32

 4/17 Enolate chemistry. Epimerization, halogenation, and alkylation of the alpha carbon.   22
33 4/19 The aldol condensation reaction. Kinetic vs Thermodynamic Enolates.   22
34 4/22 Stork enamine synthesis. Acetoacetic ester and malonic ester syntheses.   23
35 4/24 Claisen condensation. Michael addition.   23
36 4/26 Robinson annulation and related reactions.   23
37 4/29 Amines. Properties and synthesis.   27
38 5/1 Reactions of Amines.   27
  5/3 Exam 4   22, 23, 27
  5/9 Final Exam