[Western Oregon University]


CH 334 Organic Chemistry

Fall 2007

Instructor: Dr. Arlene Courtney, NS 112
Office Hours: MWF 9-10, W 10-11, 1-2 Th 11-11:30
Office Telephone: (503) 838-8207
Email: courtna@wou.edu
Texts: Smith, "Organic Chemistry", 2nd Edition
Study Guide to accompany Smith
Zubrick, "The Organic Chem Lab Survival Manual
Other Materials:

Bound Laboratory Manual with carbon copy pages
Molecular Model Set

Laboratory Aids

Course Description: This course will cover the organic chemistry of alkanes and alkyl halides emphasizing their structures, properties, and reactions. The prerequisite for this course is successful completion of Ch 223 or consent of the instructor.
Special Note:

This is the first course in the year long organic chemistry sequence. Students completing the sequence will be required to take the American Chemical Society organic chemistry exam as the final exam for Ch 336. This is a standardized examination.

Learning Objectives: By the time you have finished the entire organic chemistry sequence, you should be able to look at an organic molecule and predict how it will behave in a given chemical environment. The most important consideration in making such predictions is where the electrons are located in the molecule and where they would like to go. All of organic chemistry can be explained by following the movement of electrons. In Ch 334 you will learn:
  • how atoms bond together in organic molecules
  • to determine the 3-D structures of organic molecules
  • to compare the structures of organic molecules in terms of their potential energies
  • locate potentially mobile electrons in molecules
  • to recognize sites of polarity in organic molecules
  • to predict physical properties such as boiling point, melting point and solubility based on electronic structure
  • to draw and name members of the alkane and alkyl halide classification
  • to predict the mechanism of a nucleophilic substitution reaction


Date Topic Text Reading Homework Problems (Text) Other Assignments
9/24 Lewis Structures

The Golden Rules of Organic Chemistry

Practice Quiz
Ch 1: 1.1-1.4 1.37-1.40, 1.42-1.47, 1.51

Ionic and Covalent Bonding

Ionic, Covalent & Polar Bonding

Lewis Dot Structures

Unshared Pairs & Formal Charges

Lewis Structures from Condensed Molecules

9/26 Shapes of Molecules Ch 1: 1.5-1.7 1.54-1.57, 1.59, 1.61, 1.62


Importance of Structural Formulas

Excellent Compound Structure & Representation Tutorial

Bonding In Organic Molecules

Conversions to Line Drawings

Conversions From Line Drawings

VSEPR Theory

VSEPR Theory

Some VSEPR Problems




Hybridization Ch 1: 1.8-1.9 1.63-1.65, 1.67 Molecular orbitals symplified

Excellent orbital tutorial

Atomic & Molecular Orbitals

Valence & Hybridization



1.10-1.13 1.68, 1.70-1.74, 1.76-1.80, 1.83




Acid-Base Concepts

2.1-2.4 2.28-2.37 Lewis Acids and Bases

Acid-Base Tutorial

10/03 Acid Strength

Ch 2: 2.5-2.7 2.38-2.41, 2.45, 2.47  
10/05 Lewis Acids and Bases
 Ch 2: 2.8 2.49-2.53, 2.57 Lewis vs. Bronsted

Nucleophilicity vs. Basicity
10/08 Intermolecular Forces

Ch 3.1-3.3  3.15- 3.18, 3.20

Intermolecular Forces

Intermolecular Forces

Intermolecular Forces (Flash Show)



Ch 1-2

    Exam Study Aids
10/15 Physical Properties

Ch 3: 3.4-3.9 3.21-3.36, 3.38, 3.41  
10/17 Alkanes: Nomenclature

Ch 4: 4.1-4.6 4.37, 4.40, 4.42-4.46

Flowchart for Naming Alkanes

Constitutional Isomerism & Alkane Nomenclature

Alkane Nomenclature Tutorial

Cycloalkane Nomenclature

Alkane Nomenclature Problem Sets:I, II

Physical Properties of Alkanes

10/19 Conformations of Acyclic Alkanes

Ch 4:4.7-4.10 4.47-4.50, 4.53 Torsional Strain Tutorial

Alkane conformations

Ethane, butane
10/22 Conformations of Cyclic Alkanes

Ch 4: 4.11-4.13 4.54 Cis-trans Isomers on Cyclohexane Rings Tutorial

Conformations of Alkanes & Cycloalkanes

Conformational Stability

10/24 Conformations of Cyclic Alkanes   4.55- 4.59  


Chemical Properties of Alkanes Ch 4: 4.14-4.15 4.62-4.64  


Ch 3-4

    Exam Study Aids

10/31 Introduction to Stereochemistry

Ch 5: 5.1-5.3 5.33

Identifying Isomers



Last Day to Drop Without a Grade

Ch 5: 5.4-5.6 5.34-5.37, 5.40-5.44, 5.46 Excellent Stereochemistry Tutorial

Single stereocenters




 Ch 5: 5.7-5.11  5.48-5.50, 5.52, 5.55,-5.58  Multiple stereocenters

Roadmap for Classification of Isomers

Stereochemistry Online


Properties of Stereoisomers

Ch 5: 5.12-5.13 5.59-5.61  Stereochemistry Simplified
11/09 Introduction to Organic Reactions  Ch 6: 6.1-6.4 6.23-6.26  



Energy Diagrams

Ch 6: 6.5-6.11 6.39-46.45, 6.48

Energy Diagrams

It's all about the Pi Bond


Alkyl Halides

Ch 7: 7.1-7.5 7.41-7.45

Alkyl Halide Nomenclature

Carbocation structure

Carbocation stability

Carbocation Rearrangements



Ch 5-6

    Exam Study Aids
11/19 Nucleophilic Substitution

Ch 7:7.6-7.8 7.46-7.52,7.54
Lab Aids

SN2 Reactions

Ch 7: 7.9-7.12 7.55-7.58  Animated SN2 Reaction
11/26 SN1 Reactions

Ch 7: 7.13-7.16 7.59-7.64  Carbocations
11/28 SN1 or SN2?

Ch 7: 7.17-7.18 7.68, 7.70, 7.71
11/30 Introduction to Organic Synthesis

Ch 7: 7.19 7.73-7.76  


There are NO alternate examination times


MIDTERM EXAMS 3@100 pts 300 pts A: 600-540 pts

B: 528-480 pts

C: 468-420 pts

D: 408-360 pts

F: Below 348 pts
QUIZZES 5@20 pts 100 pts
FINAL EXAM   100 pts
LABORATORY   100 pts
  TOTAL 600 pts


Short quizzes will be given on the days denoted by the symbol . Quizzes will be given promptly at 8 am. No makeup or late quizzes will be given; missed quizzes are covered by your allowed dropped scores . The top 5 scores will be used in determining your grade.


You are expected to have completed the reading assignment given for a particular date before coming to lecture on that date. The homework problems are intended to be completed after the lecture on the date listed. Working the assigned homework problems is essential to success in organic chemistry. These assignments will NOT be graded by the instructor. It is best to have read the textbook and studied the lecture material before attempting the homework assignments. Try to work each problem as if it were a question on an examination. If you cannot answer the problem correctly, go back and reread the text and your lecture notes pertaining to the topic.


Direct suggestions, comments, and questions about this page to Arlene Courtney
Last Modified November 26, 2007

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