TEXTS

1. Organic Chemistry, 8th ed., Graham Solomons & Craig Fryhle
2. The Organic Chem Lab Survival Manual, 6th ed., Zubrick
(Recommended) Study Guide to Organic Chemistry, 8th ed., 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

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 Disabilities Gordon College is committed to assisting students with documented disabilities. (See Academic Catalog Appendix C, for documentation guidelines.) A student with a disability who may need academic accommodations should follow this procedure: Meet with a staff person from the Academic Support Center (Jenks 412, x4746) to: make sure documentation of your disability is on file in the ASC, discuss the accommodations for which you are eligible, discuss the procedures for obtaining the accommodations, and obtain a Faculty Notification Form. Deliver a Faculty Notification Form to each course professor within the first full week of the semester; at that time make an appointment to discuss your needs with each professor. Failure to register in time with your professor and the ASC may compromise our ability to provide the accommodations. Questions or disputes about accommodations should be immediately referred to the Academic Support Center. See Grievance Procedures available from the ASC.

USEFUL WEB RESOURCES

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.

Date	Reading   (before class)	Topic
Aug 24	---	Syllabus and Introduction
Aug 26	1.1-7	Carbon, bonds & charge
Aug 29	handout calculator	NO CLASS TODAY Review of chemical calculations due on Wednesday
Aug 30		No lab this week
Aug 31	1.9-14 1.16,17, 2.1-4	Orbitals and hybridization Molecular geometry; Representation of molecules
Sep 2	2.5.9	Structure vs. behavior: Introduction to functional groups
Sep 5	---	NO CLASS TODAY Labor Day
Sep 6	1, 2, handout #1 handout #2	Check-in, Orientation; "Powers of Observation"
Sep 7	2.10-13	Carbonyl compounds
Sep 9	2.14,15	Relationships Between Physical Properties and Molecular Structure
Sep 12	3.1-6	Acidity and Basicity
Sep 13	34, handout, Solomons 2.16	Infrared Spectroscopy: Functional group probe
Sep 14	3.12-15	Acids and bases in organic chemistry
Sep 16	4.1-7	Alkanes: Nomenclature and Properties
Sep 19	4.1-7	Alkanes: Nomenclature and Properties
Sep 20	3,12, handout	Melting Point Determination and Significance
Sep 21	---	Synthesis, Backwards first!
Sep 23	4.16-19	Synthesis, then Forward!
Sep 26	---	Catch up and preparation for opportunity
Sep 27	4, 19, 20 (class 1), handout	Simple Distillation Boiling Point Determination
Sep 28	---	* * * OPPORTUNITY #1 * * *
Sep 30	4.8,9	Conformational analysis of linear alkanes
Oct 4	4.10,11	Ring strain
Oct 5	4, 19, 20 (class 3), Dist. handout TopoCalc handout	Fractional Distillation Topological Indices as Predictors of Physical Properties
Oct 5	4.12-14	Conformational analysis of cyclohexanes
Oct 7	5.1-6	Stereochemistry: Chirality
Oct 10	5.7	Stereochemistry: Nomenclature
Oct 11	6, 9, 11, 13, 17, 18, handout	Synthesis and purification of an organic solid
Oct 12	5.8-11	Stereochemistry: Optical activity
Oct 14	---	No class, quad break
Oct 17	5.12-14	Conclusion, Stereochemistry
Oct 18	3, handout	Using the Chemical Literature Drawing Structures with ChemSketch, (download now)
Oct 19	6.1-4,14	Reaction types: Nucleophilic substitution
Oct 21	6.5-8	Mechanism: The SN2 mechanism
Oct 24	6.10-12	The SN1 mechanism
Oct 25	20 (class 3), handout	Dehydration of 2-Methylcyclohexanol
Oct 26	6.13	Competition: SN2 vs. SN1
Oct 28	6.15-19	Competition between types: Substitution vs. Elimination
Oct 31	7.1-4	Alkenes and alkynes: Nomenclature and stability
Nov 1	---	GC of dehydration product
Nov 2	7.5-8	Alkene synthesis: Zaitsev's rule
Nov 4	7.9-11	Alkyne synthesis
Nov 7	7.12-14	Hydrogenation revisited
Nov 8	---	No lab: Day of prayer
Nov 9	---	Catch up and preparation for opportunity
Nov 11	---	* * * OPPORTUNITY #2 * * *
Nov 14	8.1-5	Alkenes and alkynes: Ionic addition; Markovnikov's rule
Nov 15	handout	Green chemistry: Bromination of an alkene
Nov 16	8.6	Oxymercuration/demercuration
Nov 18	8.7-11	Organoborane chemistry
Nov 21	8.12-14	Alkene halogenation
Nov 22	---	Catch-up all unfinished IR/GC/melting points
Nov 23	---	No class, Prepare for Thanksgiving
Nov 25	---	No class, Recuperate from Thanksgiving
Nov 28	8.15-17	Alkene reactions with carbene; Oxidation
Nov 29	handout	Synthesis of an alkyne: Diphenylacetylene
Nov 30	8.18-21	Alkyne reactions
Dec 2	11.1-6,10	Alcohols: Reactions involving the O-H bond
Dec 5	11.7-9,11,13	Alcohols: Reactions involving the R-O bond Ethers
Dec 6	---	Laboratory Exam; Check-out
Dec 7	11.12,14,15,17	Ether reactions
Dec 13	2:00 - 4:00pm	* * * OPPORTUNITY #3 * * *