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.

Since the ability to communicate effectively is a key to success in scientific endeavors, a writing assignment (the Green Organic Literacy forum, or GOLum) is an important element in this course. GOLum will engage a team of several students in the preparation of a useful end product to communicate the principles of green chemistry to an audience external to this course. Important note: this is not a standard research paper. Please refer to the section below which describes the style of the assignment before proceeding! A list of possible topics/audiences is provided; however, individual interests may be pursued with permission. While content is extremely important, this assignment will also be evaluated in terms of form of presentation. Due to the complexity of this project, several intermediate milestones are due (sse handout). Failure to observe these due dates will result in a one-half letter grade reduction in the final project grade for each milestone missed. Handwritten milestones will not be accepted. The final project is due as shown on the Class Schedule below. Late submissions will be penalized one letter grade for each day (or portion thereof) late - "Big mistake. Big. Huge."

Three Opportunities will be administered on the dates listed below. Make-ups will be given only under extreme circumstances (illness, serious personal difficulty). Opportunity #2 is a take-home, open-book assignment which will require a great deal of time on the week of March 20 to March 27. Please arrange to have a minimum of 10 hours to devote to this assignment. Individual students sometimes choose to work far beyond this suggested amount of time.

The final examination will be a multiple choice standardized American Chemical Society examination which is cumulative over both courses. Any student scoring at the national 90th percentile or higher on the this exam will automatically receive a grade of A in the course provided all laboratory work has also been completed.

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:

      30% - Three Opportunities
      15% - Quizzes (drop three low scores)
      20% - Laboratory (includes lab exam)
      20% - GOLum
      15% - Final examination (curved)

GREEN ORGANIC LITERACY FORUM (GOLum) ASSIGNMENT

As you know, the concepts of green chemistry are vital to the development of sustainable chemistry. 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 which 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.

Three elements are important as you begin to approach this assignment.

1. You must form a team. A team will consist of 3-4 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 partner has many of the same free times as you. You should also find that your partner's learning style and working habits complement your own.

2. You must choose a target audience. Use your creativity to find 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. For example, your presentation may be much more effective to a group of chemists than to a group of friends who meet to hear your work. Some possible audiences are:

   • home schooling parents
   • high school educators
   • high school students
   • college education majors
   • future CH211/212 classes
   • general campus (posters, presentations, articles, lectures, events)
   • general public (posters, presentations, asrticles)
   • college educators (poster presentation at ACS national meeting)
   • publication in professional journal

3. 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. The following ideas occur to me as I prepare the syllabus:

   • New Hope Tutorials - already underway
   • Beyond Benign Fellows high school/museum outreach - already underway
   • Green Chemistry, Video project for use in high school outreach
   • Rotating display cases, for example:
     • Presidential Green Chemistry Challenge - Green Chemistry Honored
     • From Silent Spring to Green Chemistry, A historical development
     • E-Factor - Measuring waste
     • From waste cooking oil comes ... Green Chemistry Revealed
   • Outreach-in-a-Box (EPA grant activity)
   • Hamilton-Wenham Community House after school program
   • Green chemistry lecture series
   • Green Chemistry ACS Student Affiliate Chapter jumpstart
   • Green Chemistry Through the Eyes of Faith; publication project
   • GOLum evaluation metaproject, Publication in research journal expected
   • Green Chemistry research project with a faculty collaborator, presentation and, possibly, publication expected
     • Benign oxidation of alcohols to aldeyhde/ketone Green Chem., 2007, 9, 421-423
     • Bismuth mediated hydration of an alkene, Research startup
     • Synthesis of Hantsch 1,4-dihydropyridines by fermenting bakers yeast, Jung Hwan Lee, Tetrahedron Letters 46 (2005) 7329-7330
     • Large scale Biginelli reaction via water-based biphasic media: a green chemistry strategy, Ajay K. Bose, Tetrahedron Letters 46 (2005) 1901-1903
     • Others?...

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. With the exception of direct quotations, you are encouraged not to use footnotes/endnotes since they detract from the readability1 of your work. 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.

Several important dates apply to the various milestones in this project. The timely submission of all items is essential to success in the project. Details of the milestones follow. Milestones will only be accepted electronically (unless previously arranged) by submission to greenchemistry@comcast.net 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

1. January 28 - Team organization

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. Present three or more possible projects ranked from your favorite ideas to your least favorites.

2. February 18 - Annotated Bibliography

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.

Several journals have emerged which are specifically devoted to green chemistry, most notably Green Chemistry, published by the Royal Society of Chemistry. 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.

3. February 27 - Forum Plan

Describe exactly who your presentation is directed toward (not in general, but specifically) and how you have arranged to communicate your work to your audience. Include copies of any communications between yourself and the audience representative. In the case of verbal communications, include a summary of the conversations. Include a one page summary, describing the purpose of your presentation and an outline of the actual content you wish to include.

4. March 23-25 - Critique of Draft by classmates

This milestone requires a complete project; however, instead of making your presentation to your target audience you will present the information, in its complete form, to another team in the class. The evaluating team will critique your work using a guide sheet provided by the professor. A written summary of this evaluation will be sent to your team (with a copy to greenchemistry@comcast.net) no later than Friday, March 27.

5. April 27 - Project completed and submitted in a binder with all relevant materials:

Name of project amd team members Brief bio statements (with photos) and abstract	1 page maximum
Description of the audience	about 1 page
Description of the presentation forum	about 1 page
Mirror: Copies of all material presented for the audience	variable, 5-15 pages
Updated annotated bibliography	variable, 1-10 pages
Critique, analysis of outcomes, suggestions for future work	1-2 pages

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. Really. We drop low quiz scores, though.

Students with disabilities who may need academic accommodations should follow this procedure: Contact Ann Seavey in the Academic Support Center (Jenks 412, x4746) to make sure documentation of your disability is on file in the Academic Support Center. (See Academic Catalog Appendix C, for documentation guidelines.) Meet with an Academic Support Center (ASC) staff person to discuss the accommodations for which you are eligible and the procedures for obtaining them. Obtain a Faculty Notification Form from the ASC and deliver it your professor within the first full week of the semester. Set up a follow-up appointment to discuss your needs with your professor. Your failure to register in time with your professor and the ASC may compromise our ability to provide the accommodations, so please follow the above procedure. Questions or disputes about accommodations should be immediately referred to the Academic Support Center. Gordon College is committed to assisting students with documented disabilities. If you have a disability, it is essential that you obtain appropriate documentation of the disability and that you understand the accommodations, appropriate to the specific disability, to which you are entitled.

USEFUL WEB RESOURCES

PRACTICE EXAMINATIONS (EXTERNAL WEBSITES)

Note: Laboratory is preceeded by a mandatory pre-lab lecture. Reading: 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.

Meeting	Reading	Topic
Jan 20	handout	Check-in Light as reagent: Photochemical synthesis of benzopinacol
Jan 27	handout	Sodium borohydride reduction of a ketone: Preparation of meso-hydrobenzoin
Feb 3	handout	The Grignard synthesis of a 3° alcohol: Synthesis of triphenylmethanol by two methods with "green-ness" comparisons
Feb 10	handout	TBA: Multicomponent reactions: Synthesis of a β-acetamidoketone
Feb 17	handout (in class)	Aqueous Diels-Alder reaction
Feb 24	handout	Electrophilic aromatic substitution: Iodination of an arene
Mar 3	handout	Workup of iodovanillin
Mar 17		TBA - Please Check Back!
Mar 24	Solomons ch. 9	NMR lecture video Problem solving with NMR spectra Homework, Read textbook 9.1-9.11C (skip 9.5, 9.9D) Practice homework: chapter 9.28 DUE ON FRIIDAY AS PART OF OPPORTUNITY #2: Link
Mar 31	handout	Preparation of biodiesel
Apr 7	handout	Claisen condensation: Preparation of dibenzalacetone
Apr 14	handout	TBA: Alkene metathesis, Green aldehyde preparation, or Green carbonyl reduction
Apr 21	handout	Thiamine-catalyzed benzoin condensation
Apr 28	---	Laboratory Exam; Check-out
May 5	---	Disruption of Space/Time Continuum Tuesday becomes Thursday at Gordon College No lab today

ENDNOTES

1. See? They really do detract from readability. : )