Organic Chemistry I

Chemistry 2313

Fall 1998

Dr. James E. Hanson

Lecture: MWF 10:00-10:50 McNulty 219

421 McNulty



Laboratory: MW, 3:00-5:50 PM


McNulty 223


Office Hours: MW 1:30 - 3:00 PM


or by appointment


Organic Chemistry, Joseph M. Hornback

Techniques and Experiments for Organic Chemistry, 6th Edition, Addison Ault

Supplemental Materials

molecular model kits (recommended, not required)


Students who successfully complete this course will learn the structures and nomenclature, and the chemical, physical, and spectroscopic properties of organic compounds, primarily the hydrocarbons, halogenated organic compounds, alcohols, and ethers. They will learn the reactivities of these classes of compounds, and will be able to predict products when given starting materials and to suggest appropriate routes of synthesis. They will understand these reactivities using reaction mechanisms and energetics and simple theories of resonance and electrostatic stabilization. They will apply this knowledge in the laboratory, where they will learn the techniques of both synthesis and analysis in organic chemistry. Above all, the successful student will have learned to think synthetically and analytically about problems in organic chemistry, and will not rely solely on rote memorization.



3 x 100 = 300 points


100 points

Final Examination

150 points

Literature Projects & Assignments

100 points


150 points


800 points


All grades will be assigned based on a renormalization protocol. The high grade in the class will be assigned a value of 100% and all other percentages will be calculated from this norm. The scale will be the standard scale with an A > 90%, a B 80-89.9%, etc.

Note that since the normalization value (the high score) will not be known until grades for all components of the course are complete, it is difficult to define a grade with any accuracy until the end of the course.


Learning organic chemistry requires consistent effort. To encourage and promote this effort, an assignment or quiz will be given about once a week. As the lowest quiz grade will be dropped, there will be no make up quizzes. Three one hour exams will be given during the semester. Each will emphasize the most recent material, but as knowledge gained earlier in the course (and in prior prerequisite courses) may be necessary for understanding the problems, all exams can be considered essentially comprehensive. Exams will be short answer questions and problems, there will be no multiple choice. Exams will be scored and returned within one week. Upon return, the exam scores will be open for discussion for one week. Except for arithmetic mistakes, exams will only be re-scored in their entirety by the instructor: individual problems will not be re-scored. The final exam will be comprehensive. No make up tests will be given. In the event that an exam must be missed due to a documented medical or other legitimate emergency, the 100 point value of that exam will be added to the final exam. Sets of suggested problems from each chapter will be provided by the instructor. These problems should be worked, but will not be collected. Answers to these problems can be found in the study guide.

Academic dishonesty will NOT be tolerated. Any student found cheating on an exam or quiz or plagiarizing or falsifying a laboratory notebook will be given a zero for that exam, quiz, or lab. A letter describing the offense will then be placed in that studentís permanent record. A second infraction will result in dismissal from the course and a failing grade.


Safety: The laboratory contains many potential hazards and safety must be taken extremely seriously. Failure to observe safe operating procedures will result in expulsion from the laboratory for the day. A second safety violation will result in permanent expulsion and a zero for the laboratory portion of the grade. Appropriate attire is required at all times in the laboratory as part of safe laboratory practices. This begins with safety glasses and includes long pants or skirts. Shorts, bare feet, and open-toed sandals are NOT permitted. Lab coats and gloves are recommended.

Preparation and Notebook Keeping: Preparation is essential for safety and efficiency in the laboratory. No one will be permitted to work in the lab who has not documented their preparation in the laboratory notebook. This pre-lab preparation will be checked at the beginning of each lab period. As is the practice in all industrial and research laboratories, the notebook will be the primary document for the laboratory. (Most students will have learned how to maintain a laboratory notebook in General Chemistry. Those who have not should purchase Writing the Laboratory Notebook by H.M.Kanare, available in the bookstore.) Notebooks will be collected and graded every third or fourth week.

Grading: The grade for the laboratory will be based on the laboratory notebook, performance in the laboratory, and on a written report over the multi-step synthesis. The lab grade will be based approximately 40% on the notebook, approximately 30% on laboratory performance, and about 30% on written reports.


Approximate Date

Tentative Topics

9/30 - 10/7

chapters 1-6

10/30 - 11/9

chapters 6-9

12/11 - 12/14

chapters 9-10, 12-13

FINAL: December 15, 12:45 PM


Last day for withdrawal: October 23

Schedule of Lecture Topics

Introduction (Chapters 1 & 2)

Orbitals & Bonding (Chapter 3)

Acids and Bases (Chapter 4)

Functional Groups (Chapter 5)

Stereochemistry (Chapter 6)

Nucleophilic Substitution (Chapter 7)

Elimination (Chapter 8)

Synthesis (Chapter 9)

Addition (Chapter 10)

Spectroscopy (Chapters 12 & 13)

Schedule of Laboratory Experiments

(Schedule subject to adjustment.)

Laboratory meets Monday and Wednesday in 223 McNulty

Week 1

Check in; Laboratory Safety (Section 1), Recrystallization (Section 9)

Week 2

Distillation (Section 10)

Week 3

Extraction (Section 14), Chromatography (Section 15.1-15.4)

Week 4

Limonene (E10), Optical Activity (Section 21)

Week 5

Review Session for Exam I, Study Sections 6 & 31-39, Make-Up

Week 6

Piperene (E6), Resolution (E12)

Week 7

Cyclohexyl Bromide (E19)

Week 8

Gas Chromatography (Section 15.7), Competitive Substitution (E28)

Week 9

Cyclohexene (E17 or E18), Molecular Modeling (handout)

Week 10

Review Session for Exam II, Make-Up

Week 11

Grignard Reagents (E37 or E38), Dixanthylene (E84)

Week 12

Luminol (E87), Steroid Transformations (E88)

Week 13

Steroid Transformations (E89)

Week 14

Steroid Transformations (E90 and E91)

Week 15

Review for Exam III and Final, Check Out

No laboratory on the following days: 9/7, 10/12, 11/25