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
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 a class forum will be made available on the Gordon College GO web site. More details will be provided as they are relevant.
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.
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 2 | 1, 2, handout #1 handout #2 | Check-in, Orientation; "Powers of Observation" |
| Sep 3 | 1.9-14 | Orbitals and hybridization |
| Sep 5 | 1.16,17, 2.1-4 | Molecular geometry; Representation of molecules |
| Sep 8 | 2.5.9 | Structure vs. behavior: Introduction to functional groups |
| Sep 9 | 3,12, handout | Melting Point Determination and Significance |
| Sep 10 | 2.10-13 | Carbonyl compounds |
| Sep 12 | 2.14,15 | Relationships Between Physical Properties and Molecular Structure |
| Sep 15 | 3.1-6 | Acidity and Basicity |
| Sep 16 | Lab cancelled | |
| Sep 16 | 34, handout, Solomons 2.16 | Infrared Spectroscopy: Functional group probe |
| Sep 17 | 3.12-15 | Acids and bases in organic chemistry |
| Sep 19 | 4.1-7 | Alkanes: Nomenclature and Properties |
| Sep 22 | 4.1-7 | Alkanes: Nomenclature and Properties |
| Sep 23 | 4, 19, 20 (class 1 & 3), handout | Simple and Fractional Distillation |
| Sep 24 | --- | Synthesis, Backwards first! |
| Sep 26 | 4.16-19 | Synthesis, then Forward! |
| Sep 29 | --- | Catch up and preparation for opportunity |
| Sep 30 | 6, 9, 11, 13, 17, 18, handout | Synthesis and purification of an organic solid |
| Oct 1 | --- | * * * OPPORTUNITY #1 * * * |
| Oct 3 | 4.8,9 | Conformational analysis of linear alkanes |
| Oct 6 | 4.10,11 | Ring strain |
| 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 24 | 34, handout, Solomons 2.16 | Infrared Spectroscopy: Functional group probe |
| Oct 15 | 5.8-11 | Stereochemistry: Optical activity |
| Oct 17 | --- | No class, quad break |
| Oct 20 | 5.12-14 | Conclusion, Stereochemistry |
| Oct 21 | 20 (class 4), handout | Steam Distillation of Clove Oil Supplementary Reading (optional): Ethnopharmacology |
| 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 | 10, 15, handout | Isolation of Clove Oil |
| Oct 28 | handout | Effect of solvent on rate of an SN2 reaction |
| 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 | 3, handout | Using the Chemical Literature Drawing Structures with ChemSketch, (download now) |
| 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 26 | 20 (class 3), handout | Dehydration of 2-Methylcyclohexanol |
| Nov 12 | --- | Catch up and preparation for opportunity |
| Nov 14 | --- | * * * OPPORTUNITY #2 * * * |
| Nov 17 | 8.1-5 | Alkenes and alkynes: Ionic addition; Markovnikov's rule |
| Nov 18 | --- | No lab: Day of prayer |
| Nov 19 | 8.6 | Oxymercuration/demercuration |
| Nov 21 | 8.7-11 | Organoborane chemistry |
| Nov 24 | 8.12-14 | Alkene halogenation |
| Nov 25 | --- | GC of dehydration product |
| Nov 26 | --- | No class, Prepare for Thanksgiving |
| Nov 28 | --- | No class, Recuperate from Thanksgiving |
| Dec 1 | 8.15-17 | Alkene reactions with carbene; Oxidation |
| Dec 2 | handout | Green chemistry: Bromination of an alkene |
| 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 15 | 10:30am - 12:30pm | * * * OPPORTUNITY #3 * * * |