CHEMISTRY 201-01
ORGANIC CHEMISTRY I -
4 credits
Fall Semester, 2017

Instructor: William A. Price, Ph.D.
Office: Holroyd 345
Phone: (215) 951-1261

Section 01 M,W,F 11:45-12:35

Course Syllabus

Lab Syllabus and Schedule

Texts:

Lecture: L.G. Wade Jr., Organic Chemistry, 9th Edition, Pearson Publishing, Boston, MA, 2017. ISBN-13: 978-0-321-97137-1

Homework Assignments: www.SaplingLearning.com  - Sapling Learning Online Homework: $40.00 for 1 semester. La Salle University - CHM 201 - FALL17 PRICE (see syllabus for details)

Laboratory: The following text is required for the laboratory portion of the course:

J. R. Mohrig, C.N. Hammond, P.F. Schatz and T.C. Morrill, CHL 201-202 Laboratory Manual from Modern Projects and Experiments in Organic Chemistry, W.H. Freeman Custom Publishing, New York, 2010.

Strongly recommended: Chem-Tutor Student Modeling System for Organic Chemistry, Aldrich Chemical Co. (available from instructor)

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, neurotransmitters, antidepressants, ecstacy 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 201 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 purpose of a good textbook is to organize this vast amount of material into a few basic principles off of which many extensions and applications can be made. Our goal is to become problem solvers or diagnosticians at the molecular level - not memorizers!


Strategy:
The amount of material to be covered is quite large (over 450 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 problems from the book (as well as the workbook) as possible and ask for help when necessary. 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. You will find the study guide useful only if you attempt the problems on your own first.

Sapling Learning:

Homework will be posted on the Sapling Learning site in a timely fashion. Due dates will be posted as well. After the due date, the assignment will not be accessable for credit unless you have a reasonable excuse. There will be 10 problem sets assigned throughout the semester. They will be posted roughly a week before they are due. These may take up to two hours to complete so do not start them at the last minute. You can save your work and come back to it at a later time. A very important new skill that you will need to develop is the ability to draw molecules using the template drawing tools supplied in pertinant questions. The first week, you should do the assignments on "drawing tips shortcuts" and the curved arrow overview so that you are familiar with nuances like subscripts, superscripts, drawing Lewis structures and structures of more elaborate organic molecules (sometimes in 3 dimensions), etc.


Chapter Sequence:
We will cover chapters 1-10 in CHM 201. Chapter coverage will be 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 problems in the running text as you read the material (you may want to use a composition notebook for problems). Recommended problems are suggested throughout and at the end of the chapters and can be used to fine tune your grasp of the material.

I have posted some old examinations and problem sets. You should be aware that content coverage varies from year to year. The back exam should be used as a guide for style but not necessarily for content. You will need Adobe Acrobat to read these exercises. All lecture powerpoint slides are posted in burnt orange links. It is suggested that you download/print these and keep them in an organized notebook (2-3 per page).

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Printable Periodic Table

Organic Chemistry Tutorials from UCLA, acids/bases, formal charge, resonance, Lewis dot, curved arrows...

The ORBITRON University of Sheffield, UK - a gallery of atomic orbitals and molecular orbitals as images and animated plots

Chapter 1 - Structure and Bonding

Bonding patterns for C, N, & O

Lewis dot tutorial from UCLA

Curved Arrow tutorial with problems

Hybridization review

Resonance and Arrow Formalism / answers

Drawing Structures

 

 

Chapter 6 - Alkyl Halides: Nucleophilic Substitution & Elimination

SN1, SN2, E1, E2 ppt lecture

Allylic bromination with NBS

Allylic bromination and F.R. chlorination problems (omit q. 3) from old exams answers

Alkyl Halides from Alcohols ppt slides

Problem set for CH 6 (look at questions 1,2, and 6)

Practice SN2/E2 reactions / SN2/E2 answers

SN1 and E1 explained (including rearrangements)

SN1/E1 mechanisms

SN1/E1 mechanism answers

SN2, SN1, E2, E1 reactions from old exams answers

 

Chapter 2 - Acids and Bases

Acids and bases and more arrows / answers

Acids & Bases - helpful tutorial

Functional Groups

Chapter 1 and 2 Problems / answers

 

 

 

Alkenes - Chapter 7

Alkenes ppt slides

Alkenes problem set

Answers

 

 

Chapter 3 - Structure and Stereochemistry of Alkanes

Nomenclature

Nomenclature good naming problems answers

Conformational Analysis

Conformational Analysis some problems off old exams answers

More Newman Projection Problems / answers

3 more problems

 

 

Chapter 8 - Reactions of Alkenes

Reactions of Alkenes ppt slides

Carbocation rearrangements

Addition Reactions Tutor (adapted from F. Carey's site)

Addition reaction mechanisms oxymercuration, hydroboration, bromination, bromohydrin, both HBr additions

Ozonolysis

Alkene reactions - summary table

Chapter 8 problems addition reactions and rearrangements answers

CH 7,8 problems - Wade

 

Chapter 4 - The Study of Chemical Reactions

Organic Reactions

Free radical halogenation problem / answers

Another free radical problem / answer

Free radical chlorination problems / answers

 

 

Chapter 9 - Alkynes

Alkynes

Alkyne hydrogenation and hydration

Hydrogenation, ozonolysis problem with answer

CH 5,8-9 Problems (for CH 8-9, problems 1,4,6)

2 more H2/O3 problems

Hydrogenation and Hydration mechanisms

Synthesis exercises / answers

Chapter 5 - Stereochemistry

Stereochemistry ppt lecture

CH 5 Problems / (for CH 5, problems 2,3,5) answers

Specific rotations of known molecules

Stereochemistry problems / stereochem answers

 

 

CH 10 - Structure and Synthesis of Alcohols

Alcohols - Structure and Synthesis - ppt slides

 

Hour Exam I practice / Answers ///

Good links

Frank Carey's excellent interactive help site

Grades:
The course consists of both lecture (80%) and laboratory (20%). Your lab grade is determined by your laboratory instructor. In order to pass the course,
you must have a passing grade in both parts (>60%).
The breakdown is as follows:

4 hour exams 500 pts (50%)
Homework & Quizzes 150 pts (15%)
Final exam 150 pts (15%)
Laboratory 200 pts (20%)


A schedule of exams (roughly every 10th lecture) with probable coverage is shown below (see syllabus for details):

Wednesday, Sept. 21 Chapters 1-3.6
Friday, Oct. 14 Chapters 3.7-5
Monday, Nov. 7 Chapters 6-7
Friday, Dec. 2 Chapters 8-9

Final Exam will be held in the same classroom on the designated day and time for MWF 11:45 classes. It will be cumulative with a slight emphasis on CH 10 (new material).

Academic Calendar, 2017-2018