ORGANIC CHEMISTRY I
Chemistry 211
Gordon College, Fall 2011

Irvin J. Levy
Professor of Chemistry and Computer Science
Office Hours:
MWF, 8:30-9:30am
R, 8:30-9:30am; or by appointment

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, 10th ed., Graham Solomons & Craig Fryhle
2. The Organic Chem Lab Survival Manual, 8th ed., Zubrick
(Recommended) Study Guide to Organic Chemistry, 10th 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

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.

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 inthe 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:

  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 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:

  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:

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.

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 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. September 19 - Team organization proposal

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. December 5 - Initial 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 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.

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.

ASSIGNMENT WEIGHTS
        2% - Green Organic Literacy team proposal
        5% - Initial Annotated Bibliography
      15% - Opportunity #1
      15% - Opportunity #2
      15% - Opportunity #3 (final exam week)
      28% - Quizzes (drop three low scores)
      20% - Laboratory (includes lab exam)

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.

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



Tentative Class Schedule

For each date below, the assigned reading should be read before coming to class on that day. Occasionally we will spend more (or less) time on a topic than indicated below. Accordingly, variations in the reading schedule may occur as announced in class.

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 24---Syllabus and Introduction
Aug 261.1-7Guest lecturer: Carbon, bonds & charge
Aug 291.9-14
1.16,17, 2.1-4
Guest lecturer: Orbitals and hybridization
Molecular geometry; Representation of molecules
Aug 31


1, 2, Lab notebook handout
FW calculator

Collected Homework:
Organic Calculations
Due in one week 		No lab session today.
Read handouts and work on Chemical Calculations sheet

Aug 31---Green Chemistry video
Only available on Gordon College campus network
Sep 22.5-9Structure vs. behavior: Introduction to functional groups
Sep 5---NO CLASS TODAY
Labor Day
Sep 61, 2, handout Lab Orientation, Checkin,
Honing Observational Skills by Candlelight
Sep 72.10-13
Top 100 Drugs		Carbonyl compounds
Sep 92.14,15Relationships Between Physical Properties
and Molecular Structure
Sep 123.1-6,12-15Acids and bases in organic chemistry
Sep 133,12, handout #1
handout #2,
Solomons 2.16   		Melting Point Determination and Significance
Infrared Spectroscopy
Sep 14---Acids and bases concluded
Sep 16---Inauguration Day
Sep 194.1-7Alkanes: Nomenclature and Properties
Sep 20Handout to be distributedCups to Cleaners: A Green Chemistry Lab
Sep 21---Nomenclature concluded
Sep 234.16-19Hydrogenation; IHD
Sep 264.8,9Conformational analysis of linear alkanes
Sep 27

4, 19, 20 (class 1),
handout		Simple Distillation
Boiling Point Determination
Sep 284.10,11Ring strain
Sep 304.12-14Conformational analysis of cyclohexanes
Oct 34.12-14Conformational analysis of cyclohexanes
Oct 4


4, 19, 20 (class 3),
Distillation handout		Fractional Distillation
Oct 5---* * * OPPORTUNITY #1 * * *
Oct 75.1-6Stereochemistry: Chirality
Oct 105.7Stereochemistry: Nomenclature
Oct 11

32, handout #1
handout #2,
Solomons 2.16  		Gas Chromatography of Distillate Fractions
Infrared spectroscopy of purified fractions
Oct 12---Reaction types: Addition/Elimination/Substitution/Rearrangement
Oct 14---No class, quad break
Oct 175.8-11Stereochemistry: Optical activity
Oct 18

6, 9, 11, 13, 17, 18,
handout 		Synthesis and purification of an organic solid

Oct 195.12-14Conclusion, Stereochemistry
Oct 21---Chemical reactions: Backwards then forward
Oct 246.1-4, 14NATIONAL CHEMISTRY WEEK!
Mechanism: Nucleophilic Substitution
Oct 2520 (class 3),
traditional
Revised version 		Greener Dehydration of 2-Methylcyclohexanol
Oct 266.5-8Mechanism: The SN2 mechanism
Oct 286.10-12The SN1 mechanism
Oct 316.13Competition: SN2 vs. SN1
Nov 1

handout to be distributed Microwave Synthesis of an Ionic Liquid
Nov 26.15-19Competition between types: Substitution vs. Elimination
Nov 4---* * * OPPORTUNITY #2 * * *
Nov 77.1-4Alkenes and alkynes: Nomenclature and stability
Nov 8--- No lab: Day of prayer
Nov 97.5-8Alkene synthesis: Zaitsev's rule; Olefin metathesis
Nov 117.9-11Alkyne synthesis
Nov 147.12-14Hydrogenation revisited
Nov 15handout - See ProfessorGreen chemistry: Bromination of an alkene
Nov 168.12-14Alkene halogenation
Nov 188.1-5Alkenes and alkynes: Ionic addition; Markovnikov's rule
Nov 218.6-11Oxymercuration/demercuration
Organoborane chemistry
Nov 22web resourceThe Dose Makes the Poison: Comparative ecotoxicity

Optional: Browse the web resource:
    The Science of Chemical Safety
    Essential Toxicology
Nov 23---No class, Prepare for Thanksgiving
Nov 25---No class, Recuperate from Thanksgiving
Nov 288.15-17Alkene reactions with carbene; Oxidation
Nov 29handout - See ProfessorSynthesis of an alkyne: Diphenylacetylene
Dec 308.18-21Alkyne reactions
Dec 111.1-6,10Alcohols: Reactions involving the O-H bond
Dec 511.7-9,11,13Alcohols: Reactions involving the R-O bond
Ethers
Dec 6--- Laboratory Exam; Check-out
Dec 711.12,14,15,17Ether reactions
Dec 13TUESDAY 2:30pm - 4:30pm* * * OPPORTUNITY #3 * * *