CHEMISTRY 201
ORGANIC CHEMISTRY I
Summer Session I , 2019
Instructor: William A. Price, Ph.D.
Office: HOLR 345
Phone: (215) 951-1261
M-TH 9:00-10:45

 

Lecture Syllabus

Lecture Schedule

Lab Syllabus

Lab Schedule

Texts:

For Lecture:

L.G. Wade Organic Chemistry , 8th Edition, Pearson, Boston, MA, 2013. ISBN10 : 0-321-76841-8,   ISBN13 : 978-0-321-76841-4

Homework Assignments: www.SaplingLearning.com  - Sapling Learning Online Homework: $40.00 for 1 semester. La Salle University - CHM 201 - Summer19– PRICE

Student registration instructions: 

1. Go to  http://saplinglearning.com  and click on your country ("US Higher Ed") at the top right.

2. a. If you already have a Sapling Learning account, log in and skip to step 3.
b. If you have Facebook account, you can use it to quickly create a Sapling Learning account. Click "Create an Account," and then "Create my account through Facebook." You will be prompted to log into Facebook if you are not already logged in. Choose a username and password, then click "Link Account." You can then skip to step 3.
c. Otherwise, click "Create an Account.” Supply the requested information and click "Create My Account." Check your email (and spam filter) for a message from Sapling Learning and click on the link provided in that email.

3.  Find your course in the list (listed by subject, term, and instructor) and click the link.

4.  Select a payment option and follow the remaining instructions.

Once you have registered and enrolled, you can log in at any time to complete or review your homework assignments.

For Lab: The lab manual can be found on Canvas

taken in large part from 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.


Recommended: Molecular Visions, Molecular Model Kit (comes with text in book store) or Chem-Tutor Molecular Models from Sigma-Aldrich (available in Stockroom).

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.


Strategy:
The amount of material to be covered is quite large (over 400 text book pages) thus it is imperative that you keep up with the course. Additionally, the typical 15 week semester is compressed to 5.5 weeks. Keeping up is most easily accomplished by reading the appropriate chapter prior to attending class. This is not a course where one can effectively cram immediately prior to an exam – you must work day to day. Read the assigned sections before class, take good notes then go home and recopy these notes while comparing the information to the textbook. Work through each example. Repetition is extremely important. It takes time to master some of the difficult concepts and going back over certain ideas will make them much easier to comprehend. In addition, new ideas that you learn later in a chapter will often make earlier concepts more understandable.

Work as many of the problems from the book as possible in addition to the Sapling homework - 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.


Chapter Sequence and Suggested Problems:
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). 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 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). I strongly recommend downloading the free plug-in MDL CHIME for excellent 3-D visualization of organic molecules.

________________________________________

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 - Introduction and Review

Bonding patterns for C, N, & O

Lewis dot tutorial from UCLA

Curved Arrow tutorial with problems

Acids and bases and more arrows / answers

Resonance and Arrow Formalism / answers

Drawing Structures

 

Chapter 6 - Alkyl Halides: Nucleophilic Substitution & Elimination

SN1, SN2, E1, E2 ppt lecture

Allylic bromination with NBS

Alkyl Halides from Alcohols ppt slides

Problem set for CH 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 - Structure and Properties of Organic Molecules

Hybridization review

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

MolView - molecule viewer

 

 

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 10 practice problems from old exams answers

Chapter 4 - The Study of Chemical Reactions

Organic Reactions

Free radical halogenation problem / answers

Another free radical problem / answer

 

 

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

 

 

Chapter 12 - Continued

Infrared Spectroscopy

IR analysis tutor from UCLA

IR overview with problems excellent site from Michigan State, good explanations and problems

IR/mass matching problems

 

Hour Exam I practice / Answers / Hour Exam II practice (Answers) / Hour Exam III practice / Answers

More practice: Hour Exam I practice / Hour Exam II practice / Hour Exam III practice / Hour Exam IV practice

Good links

Frank Carey's excellent interactive help site

Grades:
The course consists of both lecture (75%) and laboratory (25%). Your lab grade is determined by your laboratory instructor. In order to pass the course,
you must have a passing grade in both parts. The breakdown is as follows:

4 hour exams 400 pts (50%)
3 Quizzes and Homework 200 pts (25%)
Laboratory 200 pts (25%)