Chemistry 350 - Principles of Organic Chemistry I
Fall Semester 2018, Winona State University, Dr. Thomas Nalli
Date

Topics

Chapter in Klein

 PowerPoint or Models
8/27
The structural theory. Lewis and line-bond structures.
 1
8/29 Drawing line-bond structures by reference to normal valencies of elements. Formal Charge. Isomerism.
 1
8/31
VSEPR Theory and Molecular Polarity.  
 1
9/5
Valence bond theory. Hybrid orbitals. Pi and Sigma bonds.
 1
9/7
Functional group families. Condensed and skeletal structures. Naming alkanes and finding isomers.
1, 2, 4
9/10
More alkane naming and naming of simple alcohols and alkenes. Branched alkyl groups. Cycloalkane isomers.
 4
9/12
Types of carbon atoms. Resonance theory of bonding. Drawing resonance structures using curved arrows and pattern recognition.
2
9/14
Acid/base reactions. Predicting acidity: The ARIO method.
3
9/17
Predicting basicity. Predicting the direction of equilibrium. Acidic and basic functional group families.
3
9/19
Intermolecular forces and physical properties. Boling point and  water solubility.
1.12-1.13, 2.3, 4.4
9/21
Reactions of alkanes. Combustion. Finding some isomers of C5H8. Naming of dienes, cycloalkenes, and bicycloalkanes.
4.4, 8.3, 10.2
9/24 C-13 NMR. Theory and predicting number of peaks. 16
 PowerPoint
9/26 C-13 NMR. Peak Shifts and Intensities. DEPT spectra.
 16
9/28 Conformations and strain. 4
 Images of Models
10/1
Equilibrium constants and free energy, enthalpy, and entropy. Using BDEs to calculate heats of reaction.
6
10/3
Exam 1 
 1-4, 16 (C-13)
10/5
Kinetics and collision theory. Rate laws and reaction mechanisms. The SN2 and SN1 mechanisms.
6
10/8
Transition State Theory and the Hammond Postulate. Structural effects on rate; steric effects (SN2) vs carbocation stability (SN1). Effect of leaving group ability. 
6, 7
10/10
SN2 vs SN1 Rate Effects - Effect of nucleophile strength. Neutral nucleophiles. Aprotic vs protic solvents.SN2 vs SN1- Predicting which will occur. 
7
10/12
Protic solvents effect on nucleophile strength. SN2 vs SN1determining which mechanism will occur. Carbocation rearrangements.
5, 7
10/15
Mass spectrometry. Diisoptopic elements (Br and Cl), the nitrogen rule, types of fragmentation reactions.
15
 PowerPoint
10/17 Properties of enantiomers. Optical activity and specific rotation. Racemic mixtures. Optical purity and enantiomeric excess.
 5
10/19 SN2 vs SN1 stereochemistry 5, 7
10/22 Proton NMR 16
 PowerPoint
10/24 Alcohols as SN substrates. Protonated alcohols. Tosylates. 7
10/26 Discerning structural relationships. Alkenes; cis/trans vs E/Z designations. 5
 PowerPoint
10/29 Infrared Spectroscopy
 15
 PowerPoint
10/31 Exam 2
5-7, 13.9, 15 (MS) 16 (H NMR)
11/2 1,2-Elimination of Alkyl Halides. The E1, E2, and E1cb mechanisms. Zaitsev's rule and alkene stability. E2 and E1 rate effects. 8
11/5
More E2 and E1 rate effects. Predicting which elimination mechanism will be followed. Stereochemistry.
8
  
11/7 Bulky bases. Predicting the reaction and mechanism. SN2, E2, SN1, or E1.
8
11/9
Addition of HX to alkenes. Acid-catalyzed hydration. Mechanism and prediction of stereochemistry and regiochemistry. Markovnikov's rule. Anti-Markovnikov hydration through hydroboration-oxidation.
9
11/14 More on hydroboration. X2 addition and halohydrin formation.  9
  
11/16 Dihydroxylation using peracids to form epoxides. Dihydroxylation by KMnO4 or OsO4. Ozonolysis. Catalytic hydrogenation.
 9
11/19
Exam 3
 7-9, 15(IR), 16
11/26
Preparation of Alkynes. Double E2 reactions of dihalides. Deprotonation/alkylation of terminal alkynes. 
10
11/28 Reactions of Alkynes. HX addition. Hydration, Hydroboration. Keto/enol tautomerization. 10
11/30 Reactions of Alkynes. X2 addition. Hydrogenation, Ozonolysis. Multi-step synthesis using alkynes. 10
12/3
Radicals. Radical Chain Reactions. Halogenation of Alkanes.
 11
12/5
HBr Addition to Alkenes. Radical Reactions in Synthesis.
 11
12/7 Radical Reactions in Biological Systems. Polymers. 11  
12/10
 Exam 4/Final Exam
 10-11/cumulative