Winter 2016

Instructor: Dr. Arlene Courtney, DFSC 214
Office Hours: MW 9-11, W 1-2 (other hours by appointment)
Texts: Smith, "Organic Chemistry", 4th Edition
Study Guide to accompany Smith
Other Materials:

Bound Laboratory Manual with carbon copy pages (for Ch 337 which is a co-requirement unless you have previously successfully completed it)
Molecular Model Set
Laboratory Goggles

Laboratory Syllabus

Course Description: This course will cover a number of the classes of reactions which organic molecules undergo including elimination, addition, oxidation-reduction and radical reactions and the functional groups that participate in these reactions. The use of spectroscopy for structure determination will also be covered.
The prerequisite for this course is successful completion of Ch 334.


Date Topic Text Reading Homework Problems (Text) Additional Resources
1/04 Introduction to Elimination Reactions Ch 8: 8.1-8.2 8.26-8.28
1/06 Elimination Reactions

Ch 8: 8.3-8.5 8.33- 8.35, 8.37 E2 Reactions
Animated E2 Reaction


Elimination Reactions Ch 8: 8.6-8.10 8.40- 8.43, 8.46, 8.47, 8.49-51  


Relationship of SN1, SN2, E1, E2

Ch 8: 8.11 8.53- 8.55, 8.57, 8.59, 8.60 SN1 vs. SN2
Nucleophilic Substitution Reactions

1/13 Alcohols, Ethers, Epoxides: Nomenclature & Physical Properties

Ch 9: 9.1-9.5 9.40-9.42, 9.44-9.46  
1/15 Dehydration of Alcohols

Ch 9: 9.7-9.10 9.49 Carbocations
Carbocation Rearrangements
1/18 No Class - MLK Holiday      
1/20 Conversion of Alcohols to Alkyl Halides

Ch 9: 9.11-9.13 9.47, 9.48, 9.54, 9.56



Reactions of Ethers & Epoxides Ch 9: 9.14-9.17 9.65- 9.71, 9.75, 9.78  
1/25 MIDTERM #1
1/27 Introduction to Alkenes

Ch 10: 10.1-10.7 10.36-40, 10.44 Degree of Unsaturation
1/29 Addition Reactions
Ch 10: 10.8-10.11 10.45- 10.48 Addition Reaction Movie (Alkene + HX)
Testing for Unsaturated Hydrocarbons
2/01 Addition Reactions

Ch 10: 10.12-10.15 10.54- 10.59  
2/03 Addition Reactions Ch 10: 10.16-10.17 10.52, 10.53, 10.55, 10.50, 10.65, 10.66  
2/05 Organic Synthesis

Ch 10: 10.18  10.72-10.75


2/08 Introduction to Alkynes

Ch 11: 11.1-11.5  11.25 - 11.28  
2/10 Alkyne Reactions
Ch 11: 11.6-11.10 11.28 -11.33  
2/12 Reactions of Acetylide Anion

Ch 11: 11.11-11.12

11.36-11.43, 10.45, 10.46

2/15 quiz icon Reduction Reactions

Ch 12: 12.1-12.6

12.32 - 12.36

2/17 Oxidation Reactions

Ch 12: 12.7-12.14

12.39-12.45, 12.47, 12.49 - 12.55, 12.63, 12.69, 12.71



2/19 quiz icon Introduction to Radical Reactions
Ch 15: 15.1-15.3 15.32- 15.34  
2/22 MIDTERM #2
2/24 Halogenation of Alkanes

Ch 15: 15.4-15.10 15.35-15.40, 15.44, 15.45  
2/26 Radical Addition to Alkenes

Ch 15: 15.11-15.14 15.48,15.51, 15.55, 15.62, 15.63  
2/29 Mass Spectroscopy

Ch 13: 13.1-13.5    


IR Spectroscopy

Ch 13: 13.6-13.8  
IR Problems

3/03 (lab)

1H NMR Chemical Shift Ch 14: 14.1-14.5   Proton NMR Interpretation Tutorial

3/04 1NMR Spin-Spin Splitting Ch 14: 14.6-14.10



3/07 Carbon-13 NMR Ch 14: 14.11-14.12   Carbon-13
3/09 Carbon-13 NMR      



Spectroscopy Problems
    Organic Structure Elucidation Workbook
3/11 Spectroscopy Problems

Wednesday 8:00-10:00 AM (the room will open approximately 7:45 am giving you a few extra working minutes)

PROBLEM SET #3 DUE - Before taking the final exam

MIDTERM EXAMS 2@100 pts 200 pts

A: 600-546 pts

B: 528-486 pts

C: 468-426 pts

D: 408-366 pts

F: Below 348

QUIZZES 4@20 pts 80 pts
PROBLEM SETS 2@ 25 pts
1@ 50pts
100 pts
FINAL EXAM   120 pts
  TOTAL 600 pts


Short chapter quizzes will be given on the days denoted by the symbol . Quizzes will be given at 8 am. The top 4 scores will be used in determining your grade. No make-up quizzes will be given for missing class or being late to class.


During most class periods, questions will be posed during the class that you will answer using a student response device ("clicker"). These questions will serve as a review of the material covered in the video lecture. These questions are not an examination but rather intended as a review of the material. You may use your notes and discuss the questions with classmates before choosing your answers. However, if you have not studied the material sufficiently, you may not be able to answer the questions in the time alloted. Each day you can earn points on the following scale:

Points earned toward your grade = (points you earned /0.84)

You can keep track of your points.. DO NOT come to my office asking for that information. I will not calculate your participation scores until the end of the term. Since the answers to each question will be shown in the class, you should be able to determine if you earned 4, 2, 1 or no points each day!

In addition to the review "clicker" questions, you may work on problems covering the material for that day during the class. In this case, you are expected to work on those materials during the time alloted each day. This work may be done on paper or you might be asked to present a solution as a class group for all to see. You may not leave the class during this portion of the class. You also may not use this class time to study or do homework for other classes. This is your opportunity to ask questions while solving organic chemistry problems. If you do not participate fully in all parts of a class period, you will not be awarded any class participation points for that day.


You are expected to have completed the reading assignment and watched the lecture given for a particular date before coming to class on that date. Working the assigned homework problems is essential to success in organic chemistry. These assignments will NOT be graded by the instructor. In working the homework assignments, it is best to have read the testbook and viewed the lecture material first. 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. The quizzes will be based on the material covered by the homework problems.


Problem Sets are graded homework assignments not taken from the chapter homework assignments. A problem set is due at 8 am on the dates listed for it on the syllabus. A deduction of 5 points will be made for each day that the set is late, i.e., 5 pts deducted for assigments handed in from 9 am on the day due to 8 am next day; 10 pts deducted after 8 am the next day, etc. It is your responsibility to turn your assignment in on time. THERE WILL BE NO EXCEPTIONS TO THIS POLICY. Everyone will have the same amount of time to do the work.


It is your responsibility to be present at the times scheduled for exams. THERE WILL BE NO MAKEUP EXAMS GIVEN IN THIS COURSE. If you must miss an exam due to illness, the course grade will be determined by doubling the score on the final exam. The final exam will be taken only at the officially scheduled time. DO NOT SCHEDULE OTHER COMMITTMENTS FOR THE WEDNESDAY MORNING OF FINALS WEEK, YOU MUST BE PRESENT FOR THE FINAL EXAM AT THAT TIME. Do not ask to schedule the exam at an other time...NO EXCEPTIONS.

There are several drop days incorporated into the class participation schedule to accommodate illness, transportation difficulties, a lost or forgotten clicker, a non-functioning clicker, etc. There is no provision making up missed points for any lecture period. This is covered by the drop days. Frequently missing class or forgetting your clicker will be detrimental to your class participation score. There are also no extra credit assignments available to supplement class participation scores.

Co-enrollment in CH 337 is REQUIRED. If you are repeating CH 335 and have successfully completed CH 337, this requirement, with the consent of the instructor, may be waived. However, you will be responsible for attending lab during the spectroscopy portion of the term. Laboratory attendance is required. The experiments must be performed during the scheduled time period. There are no make up labs.

Cheating is a serious offense. If you cheat on any quiz, assignment or exam, the minimum penalty is a grade of zero for that work. Your conduct may also be referred to the Student Conduct Committee for assessment of a more severe penalty.

Direct suggestions, comments, and questions about this page to Arlene Courtney

Western Oregon University
Copyright 1997 Western Oregon University