ORGANIC CHEMISTRY I
Chemistry 211
Gordon College, Fall 2002


Prof. Irvin J. Levy
Office Hours:
MWF, 12:30-1:00pm, 2:00-2:30pm
T, 10:30am-12:30pm
Online study session, TBA

The two semester course in Organic Chemistry will seek to develop an appreciation of the importance of carbon chemistry in our lives and in our world. In a practical light, we will endeavor to acquire a level of expertise in the theoretical and actual manipulation of carbon compounds.

TEXTS

1. Organic Chemistry, 7th ed. upgrade, Graham Solomons & Craig Fryhle
2. The Organic Chem Lab Survival Manual, 5th ed., Zubrick
(Recommended) Study Guide to Organic Chemistry,7th ed. upgrade, Solomons & Fryhle

ADDITIONAL MATERIALS

1. Bound notebook for laboratory
2. Safety goggles as required by Department
3. Protective gloves
(Recommended) Darling Flexible Stereochemical Models

MODES OF EVALUATION

Organic Chemistry is very much like a language. As with any language, mastery is only possible with regular practice. Accordingly, homework assignments following the enclosed Class Schedule will be given daily. It is expected that the assignment will be completed before the next lecture. Homework will be assigned to help clarify important concepts; however, homework will not be collected and will not directly affect the course grade. Homework does, of course, affect the grade in that it is unlikely that the course content can be mastered without significant practice. Self-evaluation of homework will be possible through the use of the Study Guide.

A brief quiz covering recent lecture material will normally be given at the beginning of every other class period. The first quiz will occur on the fourth day of class. Regular attendance is, thus, necessary to achieve success in the course. The three lowest quiz scores will be discarded when calculating the final quiz score. Make-up quizzes will not be administered under any circumstances. All quizzes are closed-book, closed notes.

Three Opportunities will be administered on the dates listed below. Make-ups will be given only under extreme circumstances (illness, serious personal difficulty). The third opportunity will occur during the final examination period established by the registrar. This opportunity will be cumulative over all reactions covered during the semester and will also include sections regarding theory from the chapters which were not previously covered in Opportunity #1 or #2. All opportunities are closed-book, closed-notes.

Laboratory work will be assessed in the following way. A student is expected to attend all labs (or makeup assignment if missed through excusable absence), properly utilize a laboratory notebook (which will be subject to examination without notice), show evidence of preparation for lab (through lab quizzes, flowcharts, etc.), and strictly adhere to all chemical hygiene rules. It is usually very difficult to make up missed labs, thus it is essential that lab attendance be very faithful. The lab grade begins at 100% and will be decreased by 10% for each nonperformance of the expected standards. After a one time grace period (no penalty), upon violation of a chemical hygiene rule, the student will be asked to leave the lab for the remainder of the class period. This will result in two reductions to the lab grade (chemical hygiene violation, nonexcused absence).

Laboratory notebooks will be prepared by the student and will be assessed by a combination of self-evaluation and peer-evaluation (neither of which will affect the actual grade in the course) and by evaluation by the lab instructor. Students who perform all laboratory work, observe all chemical safety regulations, and maintain an acceptable laboratory notebook will receive full credit for laboratory effort (representing 67% of the lab grade). During the final laboratory session, a laboratory examination will be administered. The score on this examination represents 33% of the lab grade.

Scores on graded materials are not curved. Final grades will be computed as follows:

      45% - Three Opportunities
      30% - Quizzes (drop three low scores)
      25% - Laboratory (includes lab exam)

MISCELLANEOUS INFORMATION

This course will endeavour to make us of the computer as tool to aid communication, to enhance learning and to provide reference information. To encourage students to take advantage of this resource an online study session run by the professor will be scheduled on a weekly basis. This is made possible by use of AIM (AOL Instant Messenger). This application is available from America Online for no cost. Specific instructions will be presented in class prior to the first online study session.

Make-up examinations will be allowed only if the absence is previously cleared with the instructor or in the event of an emergency. In the case of illness, a written excuse from the health center is required. In the case of a personal emergency, a note from the Center for Student Development is required.

Make-up quizzes are not administered under any circumstances.

Students with documented disabilities must identify themselves in writing no later than the second Friday of classes in order for an accommodation to be made available.

USEFUL WEB RESOURCES

General resources

------------------------------------------------------- FOR SECOND SEMESTER ONLY --------------------------------------------------------------------------------
ChemSketch: All-Purpose Chemical Drawing and Graphics Softwaredownload
IUPAC Naming Tooldownload
Laboratory Notebook Guidelineshandout
Calculating limiting reagents and percentage yieldhandout
Aldrich Chemical Company Search Pagewebsite
ChemExper Chemical Directorywebsite
Acros Chemicalswebsite
NIST Chemistry Webbookwebsite

Special topics

Please note that these resources are all managed by other institutions. Consequently, the links may not work depending on the whim of the creators of these web resources.

IUPAC Rules of Nomenclature
WEB-ster's Organic Chemistry, A List of Lists
Visualizing Aids For Organic Chemistry
The Organic Laboratory
Named Reactions in Organic Chemistry
Basic Organic Nomenclature
Organic Structure Elucidation
NMR Made Simple
Stereochemistry Online
------------------------------------------------------- FOR SECOND SEMESTER ONLY PRACTICE EXAMINATIONS (EXTERNAL WEBSITES)
Royal Society of Chemistry - Multiple Choice Exam
    Solutions

Illinois/Chicago
UCLA
Maryland, Organic 1
Maryland, Organic 2
Wisconsion/Osh Kosh
California/Santa Cruz
Wisconsin/Madison
Nebraska/Lincoln
--------------------------------------------------------------------------------



Tentative Class Schedule


Meeting(s)  Chapter  Topic

1---Syllabus and Introduction
2-41Carbon Compounds & Chemical Bonds
5-72.1-13Representative Carbon Compounds
82.14,15Relationships Between Physical Properties
and Molecular Structure
93Acids & Bases in Organic Chemistry
10-134.1-9Alkanes: Nomenclature, Properties & Conformational Analysis
14, Sep 30---* * * OPPORTUNITY #1 * * *
15,164.10-14Conformational Analysis of Cycloalkanes
17,184.17-20Synthesis, Backwards then Forwards!
19-225Stereochemistry
23-276Reaction Mechanism & Competition:
Nucleophilic Substitution & Elimination
28-317Alkenes and Alkynes. Properties & Synthesis
32---Catch-up
33, Nov 15---* * * OPPORTUNITY #2 * * *
34-378Alkenes and Alkynes. Ionic Addition Reactions
38-4010Radical Mechanisms. Alkane Halogenation
41,42---Selected Special Topics; Preparation for Final Examination;
Retrosynthesis Redux, Selected examples.
Dec 18, 8:00-10:00am (sorry!)---* * * OPPORTUNITY #3 * * *



Tentative Lab Schedule


Laboratories during the first semester focus on development of techniques commonly used in the organic chemistry laboratory. Through these experiences we will learn to perform organic chemical reactions as well as some organic laboratory operations, such as use of ground glass chemical apparatus, melting point determination, recrystallization, decolorization, vacuum filtration, distillation (several types), extraction, drying, evaporation, gas chromatography and infrared spectroscopy.

Note: Laboratory is preceeded by a mandatory pre-lab lecture. Reading: chapter numbers below refer to reading required from The Organic Chem Lab Survival Manual before arriving on the lab day. Handouts will be provided online (links below) or in hard copy. Failure to read the required material before arrival at lab may result in a reduction in the laboratory grade. Unannounced laboratory quizzes will be used as necessary. These will be graded on a Pass/Fail basis. Passing grades will not affect the laboratory grade; however, each failing grade will reduce the final laboratory score by 1/2 letter grade.

Meeting   Reading  Topic

Sep 3


1, 2,
handout #1
handout #2
Check-in, Orientation; "Powers of Observation"


Sep 10

3,12,
handout
Melting Point Determination and Significance

Sep 17 9, 11, 13, 17,
18, handout
Crystallization: Acetanilide
Sep 24

4, 19, 20,
handout
Simple and Fractional Distillation

Oct 131, handoutGas Chromatography of Distillate Fractions
Oct 8 handout Steam Distillation of Clove Oil
Supplementary Reading (optional):
Ethnopharmacology
Oct 15

10, 15,
handout
Isolation of Clove Oil

Oct 22 handout Country Chemistry: Ma Pearl's Oatmeal Soap
Oct 29

handout

Using the Chemical Literature
Drawing Structures with ChemSketch, (download now)
Nov 5 33, handout,
Solomons 2.16  
Infrared Spectroscopy
Nov 12---* * * NO LABORATORY * * *
Nov 19handoutWilliamson Ether Synthesis, SN2 Reaction
Nov 26handout Dehydration of 2-Methylcyclohexanol
Please note: Thanksgiving Week - normal lab schedule!
Dec 3handoutGC of Dehydration Product
Dec 10--- Laboratory Exam; Check-out