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
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.
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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:
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. |
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 25 | --- | Syllabus and Introduction |
| Aug 27 | 1.1-7 | Carbon, bonds & charge |
| Aug 30 | 1.9-14 | Orbitals and hybridization |
| Aug 31 | 1, 2, handout #1 handout #2 | Check-in, Orientation; "Powers of Observation" |
| Sep 1 | 1.16,17, 2.1-4 | Molecular geometry; Representation of molecules |
| Sep 3 | 2.5.9 | Structure vs. behavior: Introduction to functional groups |
| Sep 6 | --- | l |
| Sep 7 | 3,12, handout | Melting Point Determination and Significance |
| Sep 8 | 2.10-13 | Carbonyl compounds |
| Sep 10 | 2.14,15 | Relationships Between Physical Properties and Molecular Structure |
| Sep 13 | 3.1-6 | Acidity and Basicity |
| Sep 14 | 34, handout, Solomons 2.16 | Infrared Spectroscopy: Functional group probe |
| Sep 15 | 3.12-15 | Acids and bases in organic chemistry |
| Sep 17 | 4.1-7 | Alkanes: Nomenclature and Properties |
| Sep 20 | 4.1-7 | Alkanes: Nomenclature and Properties |
| Sep 21 | 4, 19, 20 (class 1), handout | Simple Distillation Boiling Point Determination |
| Sep 22 | --- | Synthesis, Backwards first! |
| Sep 24 | 4.16-19 | Synthesis, then Forward! |
| Sep 27 | --- | Catch up and preparation for opportunity |
| Sep 28 | 4, 19, 20 (class 3), Dist. handout TopoCalc handout | Fractional Distillation Topological Indices as Predictors of Physical Properties |
| Sep 29 | --- | * * * OPPORTUNITY #1 * * * |
| Oct 1 | 4.8,9 | Conformational analysis of linear alkanes |
| Oct 4 | 4.10,11 | Ring strain |
| Oct 5 | 32, handout #1 handout #2 | Gas Chromatography of Distillate Fractions Country Chemistry: Ma Pearl's Oatmeal Soap |
| Oct 6 | 4.12-14 | Conformational analysis of cyclohexanes |
| Oct 8 | 5.1-6 | Stereochemistry: Chirality |
| Oct 11 | 5.7 | Stereochemistry: Nomenclature |
| Oct 12 | 6, 9, 11, 13, 17, 18, handout | Synthesis and purification of an organic solid |
| Oct 13 | 5.8-11 | Stereochemistry: Optical activity |
| Oct 15 | --- | No class, quad break |
| Oct 18 | 5.12-14 | Conclusion, Stereochemistry |
| Oct 19 | 3, handout | Using the Chemical Literature Drawing Structures with ChemSketch, (download now) |
| Oct 20 | 6.1-4,14 | Reaction types: Nucleophilic substitution |
| Oct 22 | 6.5-8 | Mechanism: The SN2 mechanism |
| Oct 25 | 6.10-12 | The SN1 mechanism |
| Oct 26 | 20 (class 3), handout | Dehydration of 2-Methylcyclohexanol |
| Oct 27 | 6.13 | Competition: SN2 vs. SN1 |
| Oct 29 | 6.15-19 | Competition between types: Substitution vs. Elimination |
| Nov 1 | 7.1-4 | Alkenes and alkynes: Nomenclature and stability |
| Nov 2 | --- | GC of dehydration product |
| Nov 3 | 7.5-8 | Alkene synthesis: Zaitsev's rule |
| Nov 5 | 7.9-11 | Alkyne synthesis |
| Nov 8 | 7.12-14 | Hydrogenation revisited |
| Nov 9 | --- | No lab: Day of prayer |
| Nov 10 | --- | Catch up and preparation for opportunity |
| Nov 12 | --- | * * * OPPORTUNITY #2 * * * |
| Nov 15 | 8.1-5 | Alkenes and alkynes: Ionic addition; Markovnikov's rule |
| Nov 16 | handout | Green chemistry: Bromination of an alkene | Nov 17 | 8.6 | Oxymercuration/demercuration |
| Nov 19 | 8.7-11 | Organoborane chemistry |
| Nov 22 | 8.12-14 | Alkene halogenation |
| Nov 23 | --- | To be announced |
| Nov 24 | --- | No class, Prepare for Thanksgiving |
| Nov 26 | --- | No class, Recuperate from Thanksgiving |
| Nov 29 | 8.15-17 | Alkene reactions with carbene; Oxidation |
| Nov 30 | handout | Synthesis of an alkyne: Diphenylacetylene | Dec 1 | 8.18-21 | Alkyne reactions |
| Dec 3 | 11.1-6,10 | Alcohols: Reactions involving the O-H bond |
| Dec 6 | 11.7-9,11,13 | Alcohols: Reactions involving the R-O bond Ethers |
| Dec 7 | --- | Laboratory Exam; Check-out |
| Dec 8 | 11.12,14,15,17 | Ether reactions |
| Dec 16 | 8:00 - 10:00am (sorry!) | * * * OPPORTUNITY #3 * * * |