CHEMISTRY 241 - 601

Fall Semester, 2006


University of Pennsylvania

College of General Studies

Instructor: William A. Price, Ph.D.


Teaching Assistants: Rebecca Arvary (email:, Joel Courter (email:, Tom Haimowitz (email:

Class Meetings: Tuesdays, September 12 - December 5, 2006 from 6:30-9:15 in DRL A-4.

Recitation: Three recitation sections: Tom - Tuesday, 5-6 PM in CHEM 514; Joel - Wednesday, 7-8 PM in CHEM 109; Becky - Wednesday, 9-10 AM in IAST 2000. To get to Becky's session, (Vagelos labs), enter Chem bldg, go to 2nd floor and cut across (north) to the Vagelos bldg (connected). At these sessions, assigned problems from the book and posted problem sets will be addressed. It is strongly recommended that you attend either one of these classes every week.

My Fall Semester Schedule


Texts: L.G. Wade, Jr., Organic Chemistry, 6th Edition, Prentice Hall, 2006.


Other Materials: Darling Molecular Model Set (available in Bookstore) or Chem-Tutor model kit available from instructor.


Web sites: / F. Carey's interactive site (needs MDL Chime)


Course Description and Objectives:

The area of organic chemistry is concerned with the chemistry of carbon-containing compounds. This field of chemistry is central to the areas of pharmaceuticals, petroleum, plastics, flavors, fragrances, pesticides, and life processes.Organic compounds include such molecules as cholesterol, proteins, lipids, DNA, chemotherapeutic agents, AZT, agent orange, and aspirin. Although organic compounds potentially contain many elements of the periodic table, this course will limit its coverage to those compounds containing carbon, hydrogen, oxygen, and the halogens.

It has been suggested that the properties and reactivities of organic compounds are a direct reflection of their geometries, bond strengths, and electron distribution (polarities). The course begins by reviewing atomic and molecular structure using modern orbital theories. Then, beginning with methane, the simplest organic compound, we will begin to develop the foundation of organic chemistry.

The study of organic chemistry is organized by investigating different groups or categories of compounds (these are called functional groups). All compounds in a given functional group contain a common sub-molecular portion that typically dictates the physical, chemical, and often the biological properties of the molecule. Students of organic chemistry are often overwhelmed by the number of compounds, names, reactions, and mechanisms that confront them. Perhaps the most important skill that a student can develop in CHM 241 is the ability to organize, categorize and apply. By learning an abstract concept and having the flexibility to apply it to a variety of similar situations, the amount of memorization is drastically reduced.



The amount of material to be covered is quite large (approximately 500 text book pages) thus it is imperative that you keep up with the course. Keeping up is most easily accomplished by reading the appropriate chapter prior to attending class. Work as many of the assigned problems from the book (as well as any suggested supplementary problems) as possible and ask for help when necessary. This is not the type of course where one can cram everything in the night before an exam. You may also find that rewriting your lecture notes in a less hurried (and more legible) fashion will help in your retaining and comprehending the material.


Chapter Sequence and Suggested Problems:

We will cover chapters 1-11 in CHM 241. Chapter coverage will be somewhat selective. It is the student's responsibility to know what portions of chapters are not covered in lectures and thus not covered on exams.

The text contains an excellent set of problems. It is recommended that you solve the suggested problems in the running text as you read the material (you may want to use a composition notebook for problems). Recommended problems from the chapters will be posted and can be used to fine-tune your grasp of the material.


Recommended problems from L.G. Wade, 6th edition:

Wade CH 1

Wade CH 6

Wade CH 2

Wade CH 7

Wade CH 3

Wade CH 8

Wade CH 4

Wade CH 9

Wade CH 5

Wade CH 10


I will periodically post practice exams and problem sets in addition to the assigned problems. For these, you will need

Adobe Acrobat Reader.

A link to our ambitious schedule for the semester is below. Please make note of the examination and quiz dates. The final examination is scheduled for Tuesday, December 19at 6:30 PM.

Schedule for Fall Semester, 2006

Printable Periodic Table

Chapters 1 & 2 material

Introduction ppt

Hybridization review

Bonding patterns for C, N, & O

Acids and Bases ppt

Structure and Bonding ppt

Chapter 1,2 problems for some of these you will need to read ahead a bit. answers

resonance, acid/base, arrows some practice problems answers

Drawing structures

Curved Arrow tutorial with problems / Lewis dot tutorial from UCLA

Chapter 3 - Structure and Stereochemistry of Alkanes

Conformational Analysis ppt Nomenclature ppt

Nomenclature good naming problems answers

Language of Conformational analysis (glossary from Carey)

Newman Projections and Chair conformations (some drawing tips from Carey)

Conformational analysis using CHIME Outstanding site from Dublin City University detailing open-chain and cyclic systems

Conformational analysis problems / answers

2 more conformation problems / answers

Chapter 4 - Chemical Reactions

Organic Reactions ppt

Chapter 3-4 problems

Slides from end of class - "The Study of Reactions" from U.T. Dallas

EXAM I answers

Chapter 5 - Stereochemistry

Stereochemistry ppt

Stereochemistry problems / answers

specific rotation slide (Prozac etc.)

Problem set on Stereochem posted 10/28/05 answers

Chapter 6 - Alkyl Halides

Substitution & Elimination

SN1, SN2, E1, E2 ppt

Nucleophilic Substitution overview with definitions (modified from F. Carey)

SN2 inversion

SN2 or E2?

Practice SN2/E2 reactions / answers

SN1/E1 mechanisms / answers

Flow chart

Practice Quiz 2 / answers

Quiz 2 answers

Chapters 7 & 8 - Alkenes

Alkenes ppt


Addition reactions tutor (adapted from F.Carey's site)

Nomenclature problems / answers

Alkenes problem set / answers

Allylic Bromination with NBS explanation and some problems

Addition reaction mechanisms (how things work)

Asymmetric Hydrogenation

Cyclopropanation and Epoxidation


Alkene reactions - summary table

Addition reactions chapter 8 problems answers

Exam II answers

Chapter 9 - Alkynes

Alkynes ppt

endiyne antitumor agents

Alkyne hydrogenation and hydration mechanisms

Ch. 8 & 9 practice problems / answers

H2/O3 problems / answers

Synthesis exercises



Chapter 10 - Structure and Synthesis of Alcohols

Alcohols ppt


Quiz 3 answers

Chapter 11 - Reactions of Alcohols

Reactions of Alcohols ppt



Mol4D an interactive tutorial site from University of Nijmegen, the Netherlands (requires CHIME) especially good for 1st semester material

Molecular Viewing Gallery  from Dublin City University (requires CHIME)

Practice test 1 (pdf) / answers

Practice test 2 (pdf) / answers




The grading breakdown is as follows. The point values of individual credit exercises are likely to vary somewhat from those listed below:


3 Quizzes ~210pts (30%)

2 Exams ~300pts (44%)

Final Exam ~180 pts (26%)