TEXTS

1. Organic Chemistry, 9th ed., Graham Solomons & Craig Fryhle
2. The Organic Chem Lab Survival Manual, 7th ed., Zubrick
(Recommended) Study Guide to Organic Chemistry, 9th 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 quizzes are not administered under any circumstances.

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.

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: 1. Meet with a staff person from the Academic Support Center (Jenks 412 X4746) to: a. make sure documentation of your disability is on file in the ASC, b. discuss the accommodations for which you are eligible, c. discuss the procedures for obtaining the accommodations, and d. obtain a Faculty Notification Form. 2. 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 also Grievance Procedures in Student Handbook.)

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 27	---	Syllabus and Introduction
Aug 29	1.1-7	Carbon, bonds & charge
Sep 1	---	NO CLASS TODAY Labor Day
Sep 2	1, 2, handout #1 handout #2 FW calculator	Check-in, Orientation "Powers of Observation" Review of Chemical Calculations
Sep 3	1.9-14 1.16,17, 2.1-4 Collected Homework: Organic Calculations Due in one week	Orbitals and hybridization Molecular geometry; Representation of molecules
Sep 5	2.5-9	Structure vs. behavior: Introduction to functional groups
Sep 8	2.10-13	Carbonyl compounds
Sep 9	3,12, handout	Melting Point Determination and Significance Candle lab report due (one per team)
Sep 10	2.14,15	Relationships Between Physical Properties and Molecular Structure
Sep 12	3.1-6	Acidity and Basicity
Sep 15	3.12-15	Acids and bases in organic chemistry
Sep 16	34, handout, Solomons 2.16	Infrared Spectroscopy: Functional group probe
Sep 17	4.1-7	Alkanes: Nomenclature and Properties
Sep 19	4.1-7	Alkanes: Nomenclature and Properties
Sep 22	---	Synthesis, Backwards first!
Sep 23	4, 19, 20 (class 1), handout	Simple Distillation Boiling Point Determination
Sep 24	4.16-19	Synthesis, then Forward!
Sep 26	---	NO CLASS TODAY Team synthesis project
Sep 29	---	* * * OPPORTUNITY #1 * * *
Sep 30	4, 19, 20 (class 3), Dist. handout TopoCalc handout	Fractional Distillation Topological Indices as Predictors of Physical Properties
Oct 1	4.8,9	Conformational analysis of linear alkanes
Oct 3	4.10,11	Ring strain
Oct 6	4.12-14	Conformational analysis of cyclohexanes
Oct 7	32, handout #1 handout #2	Gas Chromatography of Distillate Fractions Country Chemistry: Ma Pearl's Oatmeal Soap
Oct 8	4.12-14	Conformational analysis of cyclohexanes
Oct 10	5.1-6	Stereochemistry: Chirality
Oct 13	5.7	Stereochemistry: Nomenclature
Oct 14	No handout	A Green Metaexperiment: Comparative Ecotoxicity of Organic Solvents Optional, Browse: The Science of Chemical Safety Essential Toxicology
Oct 15	5.8-11	Stereochemistry: Optical activity
Oct 17	---	No class, quad break
Oct 20	5.12-14	Conclusion, Stereochemistry
Oct 21	6, 9, 11, 13, 17, 18, handout	Synthesis and purification of an organic solid
Oct 22	6.1-4,14	Reaction types: Nucleophilic substitution
Oct 24	6.5-8	Mechanism: The SN2 mechanism
Oct 27	6.10-12	The SN1 mechanism
Oct 28	20 (class 3), handout	Dehydration of 2-Methylcyclohexanol
Oct 29	6.13	Competition: SN2 vs. SN1
Oct 31	6.15-19	Competition between types: Substitution vs. Elimination
Nov 3	7.1-4	Alkenes and alkynes: Nomenclature and stability
Nov 4	---	No lab: Day of prayer
Nov 5	7.5-8	Alkene synthesis: Zaitsev's rule
Nov 7	7.9-11	Alkyne synthesis
Nov 10	7.12-14	Hydrogenation revisited
Nov 11	---	GC of dehydration product
Nov 12	---	Catch up and preparation for opportunity
Nov 14	---	* * * OPPORTUNITY #2 * * *
Nov 17	8.12-14	Alkene halogenation
Nov 18	3, handout	SciFinder: Using the Chemical Literature Drawing Structures with ChemSketch, (download now)
Nov 19	---	No class, Prepare for Thanksgiving
Nov 21	---	No class, Recuperate from Thanksgiving
Nov 24	8.1-5	Alkenes and alkynes: Ionic addition; Markovnikov's rule
Nov 25	handout - See Professor	Green chemistry: Bromination of an alkene
Nov 26	8.6	Oxymercuration/demercuration
Nov 28	8.7-11	Organoborane chemistry
Dec 1	8.15-17	Alkene reactions with carbene; Oxidation
Dec 2	handout - See Professor	Synthesis of an alkyne: Diphenylacetylene
Dec 3	8.18-21	Alkyne reactions
Dec 5	11.1-6,10	Alcohols: Reactions involving the O-H bond
Dec 8	11.7-9,11,13	Alcohols: Reactions involving the R-O bond Ethers
Dec 9	---	Laboratory Exam; Check-out
Dec 10	11.12,14,15,17	Ether reactions
Dec 16	TUESDAY 2:00 - 4:00pm	* * * OPPORTUNITY #3 * * *