Chemistry 350 - Principles of Organic Chemistry I
Fall Semester 2015, Winona State University, Dr. Thomas Nalli

No

Date

Topics

Chapter

PowerPoint
1 8/24
The structural theory. Review of Lewis Structures.
1.1-1.4

2 8/26
Lewis Structures and Formal Charge. Resonance structures.
1.1-1.6
 
3 8/28
VSEPR Theory and Molecular Polarity.  
1.7-1.10
 
4 8/31
Valence bond theory. Hybrid orbitals. Pi and sigma bonds.
1.10-1.12
 
5 9/2
Naming alkanes and finding isomers. Naming of Branched Alkyl Groups.
4.1-4.5
 
6 9/4
Naming of Branched Alkyl Groups. Cycloalkanes. Finding isomers of cycloalkanes, alcohols and amines. Functional group families.
4, 3.1
 
7 9/9
Intermolecular forces and physical properties.  Boiling points, melting points. Solubility.
3

8 9/11
Acid/base reactions. Predicting acidity.
2
 
9 9/14
More on predicting acidity and predicting basicity. Applying acidity predictions.
2

10 9/16 Common acids and bases. Combustion and cycloalkane stability.

3, 4

j
11 9/18 C-13 NMR 14 j
11 9/21 Conformations of cycloalkanes. Naming of bicyclic alkanes. 4 j 
12 9/23 Conformations of substituted cyclohexanes.
4

9/25 Exam 1 1-4, 14 (C-13 NMR)
 
13 9/28 Proton NMR  14 j
lab
IR 14 j
14 9/30
Proton NMR
14

15 10/2
Understanding organic reactions. Predicting equilibrium constants.
6

j
16 10/5
Kinetics and Collision Theory. Transition State Theory. The Hammond Postulate.

6


17 10/7 Mechanisms of nucleophilic substitution. SN2 and SN1 mechanisms. Kinetics. Steric hindrance and carbocation stability.
7

18 10/9 SN2 and SN1. Nucleophiles and Leaving Groups.
7
 
19 10/12
Solvent effects in SN reactions. Predicting SN2 or SN1 mechanism. Stereochemistry of SN reactions.
7
 
20 10/14
Carbocation rearrangements. SN2 reactions in synthesis.
9.9, 7
 
21 10/16 Properties of Diastereomers and Enantiomers. Optical activity. Racemic mixtures, chiral non-racemic, and achiral compounds. 5
 
22 10/19 Resolution of racemic mixtures. Other types of chiral compounds. 5
23 10/21
Mass Spectrometry
13
j

24
10/23
Lab Quizzes: MM3 and Expt 1


  10/26
Exam 2
5-7, 9.9, 13 (IR), 14 (proton NMR)
 
25 10/28
1,2-Elimination of Alkyl Halides. The E1, E2, and E1cb mechanisms. Details of the E2 transition state. Rate effects.
8
 
26 10/30
Zaitsev's rule. Predicting when the mechanism is E1 or E2. Rearrangements in E1 reactions. Bulky bases used for E2 reactions. 
8

 

27 11/2 Stereochemistry of E2 and E1 reactions.
8
 
28 11/4
Predicting the reaction and mechanism. SN2, E2, or SN1/E1. Preparation of alkynes by E2.
8
 
29 11/6
Alcohol reactions. Conversion to alkyl halides using HX, SOCl2, or PX3. Conversion of alcohols to tosylates.
9
 
30 11/9
Alcohol reactions. Acid-catalyzed dehydration. Carbocation rearrangements, Use of POCl3 and pyridine for dehydration.
9
 
31 11/13
Reaction of alcohols with strong bases to form alkoxides. Williamson ether synthesis.Naming  and Reactions of Ethers.
9.14-9.15
 
32 11/16

Epoxide ring-opening reactions. Stereochemistry and regiochemistry.
9
 

11/18 Exam 3
7-9, 13 (MS)
 
34 11/20
Addition of HX and X2 to alkenes. Stereochemistry of HX and X2 additions.
10
 
35 11/23
Alkenes
10
 
36 11/30
Alkenes
10
 
37 12/2
Alkynes
11
 
38 12/4
Alkynes
11
 
38 12/9
Exam 4
 10-11