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. We will seek to do this in ways that are consisent with the principles of green chemistry.
TEXTS
1. Organic Chemistry, 11th ed., Graham Solomons & Craig Fryhle; Amazon.com link
2. The Organic Chem Lab Survival Manual, 9th ed., Zubrick; Amazon.com link
(Recommended) Study Guide and Solutions Manual to Accompany Organic Chemistry, 11th ed., Solomons & Fryhle; Amazon.com link
ADDITIONAL MATERIALS
1. Bound notebook for laboratory (see link for example)
2. Safety goggles as required by Department
MODES OF EVALUATION
LECTURE
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. All opportunities are closed-book, closed-notes.
LABORATORY
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.
GREEN ORGANIC LITERACY PROPOSAL - The GOLum Project
During this course you will learn about green chemistry, chemistry that is designed to be safer for
human health and the environment. The concepts of green chemistry are vital to the development of a
sustainable world. Nonetheless, many chemists still know little about the principles of green
chemistry; likewise, chemistry is often viewed as a danger not a blessing by the media and others
who are not trained in the sciences. The ultimate goal of this project is to present useful materials
that will educate an audience beyond our class. This is not a simulated assignment. In order to
receive full credit you must actually spread the outcome of your work to another audience.
This is a complex project that can not be easily completed in one semester. During the first semester of our course you will do the following:
You must form a team. A team will consist of 4-5 students. The students on the team must commit to at least one day per week where they will be available to work together on GOLum for 1-2 hours. Ideally, you'll find that your partners have many of the same free times as you. You should also find that your partners' learning styles and working habits complement your own.
You must choose a target audience. Use your creativity to choose an actual audience to whom you can present your final work. Ideally this audience should have the potential to be affected in a significant way by your presentation. Some possible audiences are:
You must choose an actual topic to present. This is tightly connected to your audience. For example, the material you present to a chemical company is very different than what you might present to a chemistry teacher or the general public. Ask this important question as you brainstorm in your team: "What do we want to communicate?" Several students may receive permission to perform very similar projects. You are not competing against other students. As with the format/audience, the possibilities for the content are very wide. Here are the outreach projects that students completed last year, plus a couple of others I've been thinking about:
The majority of the work for this project typically occurs in the second semester. In the first semester you will do the following by the dates listed. All students in a team receive the same grade on each milestone. It is important to share the work equitably. Milestones will only be accepted electronically (unless previously arranged) by submission to green-chem@gordon.edu with all needed files attached. All milestones are due no later than 5pm on the due date. Submissions received after the 5pm deadline will be penalized.
Milestones
This milestone requires the formation of a team along with a work plan describing when you will meet weekly and what specific skills each team member brings to the project. Brainstorm about an audience, topic and format.
Revise your original proposal, including three or more possible projects ranked from your favorite ideas to your least favorites. Be specific.
This milestone requires the submission of a detailed list of resources that have been obtained for preparation of the forum. For each resource you must give a brief (1 paragraph) description of the article/book/website/etc. You may not simply copy blocks of text from an online source. You are to describe the article in your words, not copy its abstract! In a second paragraph you will then explain how this reference will be useful in the preparation of your forum. This is an extremely important milestone as you develop authority in your knowledge of the topic.
Please note: web sites may provide much valuable background material for your work; however, the quality of content and permanence of this
information must be considered before placing a web site into a bibliography. In general only .edu or .org web sites will be acceptable
sources. In special cases a .com web site may be appropriate. When in doubt, please ask. Specific websites that have excellent
resource material:
Several journals have emerged which are specifically devoted to green chemistry, most notably Green Chemistry, published by the Royal Society of Chemistry and Green Chemistry Letters and Reviews, published by Taylor & Francis. Both the Journal of Chemical Education and Chemical and Engineering News have each published special editions dedicated to the topic. In addition, many traditional journals include articles that support this project. Our library has several books specifically about green chemistry. You should also plan to venture beyond the confines of Gordon College and make use of the plethora of resources found in Boston. For example, the Boston University Science Library and Northeastern University Library are particularly helpful.
|
CRITICAL WARNING
Much of the reference material that you find for this work will come from the web, from journals, from magazines, from books, etc. You may not use any information from any source without including an appropriate bibliographic reference. In the cases where it is necessary to use someone else's exact words or images, you must use proper methods to attribute the work to the original authors, including a numerical endnote, following the style of the Journal of Chemical Education. There is nothing special about the need to scrupulously document resources in a research effort, but since you are producing an end product which will live beyond your professor's gradebook, it is essential to work in a manner that is consistent with academic expectations both at Gordon College and beyond. When in doubt, ask! Penalties for use of unattributed work are severe and, in flagrant cases, can result in a failing grade for the assignment or the course. |
Scores on graded materials are not curved. Final grades will be computed as follows:
A+ >97 B+ (87-90] C+ (77-80] D+ (67-70] A (93 - 97] B (83-87] C (73-77] D (63-67] A- (90 - 93] B- (80-83] C- (70-73] D- (60-63]
MISCELLANEOUS INFORMATION
Make-up quizzes are not administered under any circumstances. Ever. You are always welcome to request the quiz that you missed and you will always be able to receive feedback after you attempt the questions. You just won't receive credit. If you had several unavoidable absences on quiz days you are encouraged to bring this to the professor's attention at the end of the course. If your final grade will be changed by dropping an additional "low score" then that may be possible.
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 note from the health care provider is required. In the case of a personal emergency, a note from the Center for Student Development is required.
Academic Dishonesty Statement. "Academic dishonesty is regarded as a major violation of both the academic and spiritual principles of this community and may result in a failing grade or suspension. Academic dishonesty includes plagiarism, (see Plagiarism in Student Handbook), cheating (whether in or out of the classroom), and abuse or misuse of library materials when such abuse or misuse can be related to course requirements."
Statement on Academic Credit: "For each semester hour of credit, students should expect to spend a minimum of 2-3 hours per week outside of class in engaged academic time. This time includes reading, writing, studying, completing assignments, lab work, or group projects, among other activities."
Accommodations Statement: "Our academic community is committed to providing access to a Gordon education for students with disabilities. A student with a disability who intends to request academic accommodations should follow this procedure:1. Meet with a staff person from the Academic Support Center (ASC) and provide them with current documentation of the disability.Some accommodations need more time to arrange so communicating early in the semester is important. For more information consult the Academic Support Center webpage or email asc@gordon.edu."
2. Obtain a Faculty Notification Form from the Academic Support Center, listing appropriate accommodations.
3. Submit this form to professors and discuss those accommodations with them, ideally within the first two weeks of classes.
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 30 | --- | Syllabus and Introduction |
| Aug 31 | NO LAB | --- |
| Sep 1 | 1.1-7 | Carbon, bonds & charge Homework (after class): Textbook: 1.3, 1.11 |
| Sep 4 | --- | NO CLASS TODAY Labor Day |
| Sep 5/Sep 7 | 1, 2, Lab notebook handout FW calculator Collected Homework: Organic Calculations Due in two weeks | Lab Orientation, Checkin, Honing Observational Skills by Candlelight handout |
| Sep 6 | 1.9-11 1.16,17, 2.1-4 | Orbitals and hybridization Molecular geometry; Representation of molecules Homework (after class): Textbook: 1.14, 1.15, 1.16 Online problems; Solutions for online problems here |
| Sep 8 | 1.12-14, 2.5-9 | GOLum Milestone #1 due Structure vs. behavior: Introduction to functional groups Homework (after class): Textbook: 1.22, 1.35 |
| Sep 11 | 2.10-12 Top 100 Drugs | Carbonyl compounds Homework (after class): Take Two Assignment Additional practice with functional groups: 2.8, 2.9, 2.12, 2.15, 2.17, 2.30acd, 2.33, 2.36, 2.53 |
| Sep 12/14 | 3,12, handout | Melting Point Determination and Significance Candle Lab |
| Sep 13 | --- | GOLum Beginnings Green Chemistry lecture by Dr. John Warner video Only available on Gordon College campus network GOLum Brainstorming |
| Sep 15 | 2.13,14 | GOLum Milestone #2 due Relationships Between Physical Properties and Molecular Structure Homework (after class): Physical properties: 2.25, 2.27, 2.38, 2.46 |
| Sep 18 | 3.1-6,12-15 | Acids and bases in organic chemistry Homework (after class): Textbook: 3.1, 3.2, 3.9, 3.18, 3.20 |
| Sep 19/21 | 4, 18, 19 (class 1), handout #1 handout #2 | Simple Distillation Boiling Point Determination Laboratory Calculations - Due in class Monday |
| Sep 20 | --- | Acids and bases concluded Homework (after class): Textbook: 3.16, 3.17 Memorize Ka table as presented in class Estimate the Ka of the drugs you explored in the Take Two homework |
| Sep 22 | 4.1-7 | Lab calculations sheet due Alkanes: Nomenclature and Properties Homework (after class): 4.1 4.2, 4.5a |
| Sep 25 | --- | Special Event - Distinguished Green Chemistry Lecture (KOSC 104, 4:30PM) Nomenclature continued Homework (after class): 4.6 4.7a, 4.8, 4.23 (skip parts l, m & n), 4.28 |
| Sep 26/28 | NO LAB | --- |
| Sep 27 | --- | Nomenclature, concluded; Restrosynthetic concepts |
| Sep 29 | 4.15-17, 7.15 | Synthesis of alkanes Homework (after class): 4.19, 4.33, and Outline the synthesis of 2,2-dimethyldecane using organic reactants with six carbons or fewer as your starting materials. (click for solution) |
| Oct 2 | 4.8-10 | Conformational analysis of linear alkanes; Ring strain Homework (after class): 4.13, 4.38 (these will require a little reading beyond our lecture today) |
| Oct 3/5 | 4, 18, 19 (class 3), Distillation handout | Fractional Distillation |
| Oct 4 | 4.11-13 | Conformational analysis of cyclohexanes Homework (after class): Do the reading very carefully, then try these problems: (note - for some of these, we have not yet covered this in class! But try it out) 4.15, 4.16, 4.17, 4.18, 4.36 Optional: molinspiration structure generator To use molinspiration, draw structure and then click Galaxy 3D Generator button WARNING! This software is in development; I have discovered errors. You might, too! |
| Oct 6 | 4.12-13 | Continue chapter 4. Conformational analysis of cyclohexanes |
| Oct 9 | --- | Finish loose ends Preparation for Opportunity #1 Homework (after class): Prepare for Op#1 |
| Oct 10/12 | 30, 33 handout #1 handout #2, Solomons 2.16 | 1. Gas Chromatography of Distillate Fractions 2. Infrared spectroscopy of purified fractions |
| Oct 11 | --- | * * * OPPORTUNITY #1 * * * |
| Oct 13 | 5.1-6 | Stereochemistry: Chirality Homework (after class): 5.1, 5.4, 5.5, 5.6 |
| Oct 16 | 5.7 | Stereochemistry: Nomenclature Homework (after class): 5.9, 5.11, 5.12, 5.22, 5.36 |
| Oct 17/19 | NO LAB | --- |
| Oct 18 | 5.8-11 | Stereochemistry: Optical activity Homework (after class): 5.15, 5.40abcdefgmnopq, 5.52 (best problem ever!) |
| Oct 20 | --- | No class, quad break |
| Oct 23 | 5.12-14,16 | NATIONAL CHEMISTRY WEEK! MOLE DAY Celebrated ... The most chemical day of the year! Reaction types: Addition/Elimination/Substitution/Rearrangement Homework (after class): HW problems - click here for solutions |
| Oct 24/26 | Lab handout Using the microwave reactor | LAB: Microwave synthesis of an ionic liquid, [HMIM][I] Adapted from: Solvent-free preparation of ionic liquids using a household microwave oven" R. S. Varma and V. V. Namboodiri, Pure Appl. Chem., 2001, 73, 1309-1313. |
| Oct 25 | --- | Mechanism: SN2 Nucleophilic Substitution Homework (after class): TBA |
| Oct 27 | 6.1-4, 14 | Mechanism: SN1 Nucleophilic Substitution Homework (after class): 6.3, 6.23 |
| Oct 30 | 6.5-8 | Competition: The SN2 vs. SN1 mechanism Homework (after class): TBA |
| Oct 31/Nov 2 | 19 (class 3), traditional Revised version | Greener Dehydration of 2-Methylcyclohexanol |
| Nov 1 | 6.9-12 | Competition: SN2 vs. SN1 (continued) Homework (after class): 6.7, 6.8, 6.9, 6.10, 6.19, 6.20, 6.23, 6.25, 6.27, 6.29 |
| Nov 3 | 6.13 | Competition between types: Substitution vs. Elimination Homework (after class): TBA |
| Nov 6 | 6.15-19 | Final thoughts from chapter 6; Introducing chapter 7 Homework (after class): TBA |
| Nov 7 | NO LAB | Day Of Prayer |
| Nov 8 | --- | * * * OPPORTUNITY #2 * * * |
| Nov 9 | NO LAB | --- |
| Nov 10 | --- | GOLum Team Lunch Meet with your team to discuss goals for end of semester |
| Nov 13 | 7.1-4 | Alkenes and alkynes: Nomenclature and stability Homework (after class): Prepare for Op#2 |
| Nov 14/16 | 6, 9, 11, 13, 17, 18, handout | Synthesis and purification of an organic solid GC analysis of alkene products |
| Nov 15 | 7.9-11 | E2 vs. E1; Carbocation rearrangement Homework (after class): 7.1abcd, 7.2, 7.4, 7.6, 7.7, 7.11-7.14, 7.25, 7.26, 7.36, 7.37abcd, 7.41 |
| Nov 17 | 7.5-8 | Alkene synthesis: Zaitsev's rule; Olefin metathesis Homework (after class): TBA |
| Nov 20 | 7.12-14 | Alkyne synthesis Hydrogenation revisited Homework (after class): TBA |
| Nov 21 | NO LAB | --- |
| Nov 22 | --- | No class, Prepare for Thanksgiving |
| Nov 23 | --- | Be THANKFUL |
| Nov 24 | --- | No class, Recuperate from Thanksgiving |
| Nov 27 | 8.1-4 | Alkenes and alkynes: Ionic addition; Markovnikov's rule Homework (after class): 7.17, 7.19d, 7.21, 8.1, 8.2, 8.3, plus show how trans-2-pentene could be converted into cis-2-pentene |
| Nov 28/30 | web resource | The Dose Makes the Poison: Comparative ecotoxicity |
| Nov 29 | 8.5-10 | Oxymercuration/demercuration Organoborane chemistry Homework (after class): TBA |
| Dec 1 | 8.11-13 | GOLum Milestone #3 due Alkene halogenation Homework (after class): TBA |
| Dec 4 | 8.14-16 | Alkene reactions with carbene; Oxidation Homework (after class): TBA |
| Dec 5/7 | handout | Collect results from ecotoxicity experiment Preparation of an alkyne: Diphenylacetylene |
| Dec 6 | 8.17-20 | Alkyne reactions Homework (after class): All Chapter 8 problems: 8.1, 8.2, 8.3, 8.6, 8.8, 8.9, 8.11, 8.13, 8.15, 8.17, 8.20, 8.21, 8.26abfimn, 8.27abfghijklmn, 8.29, 8.53 |
| Dec 8 | 10.1-3,6 | Radical Reactions Homework (after class): TBA |
| Dec 11 | 10.4,5,7,10,11 | Radical Reactions Homework (after class): 10.1, 10.6, 10.7, 10.16, 10.19, 10.20, 10.29abcef |
| Dec 12/14 | --- | Laboratory Exam; Check-out |
| Dec 13 | --- | Review and Loose ends |
| Dec 18 | Monday 9:00AM - 11:00AM | * * * OPPORTUNITY #3 * * * |