ORGANIC CHEMISTRY I
Chemistry 211
Gordon College, Fall 2016


Prof. Irvin J. Levy
Office Hours:
MWF, 12:30 - 1:30 PM
T, 3:30-4:30 PM
or by appointment

Prof. Katy van Kirk, Lab section L3

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:

  1. 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.

  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. Here are the outreach projects that students completed last year, plus a couple of others I've been thinking about:

    For more ideas you may want to skim the titles of all of the GOLum projects that have been completed over the years.

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

1. September 7 - Team development

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.

2. September 16 - Team plan initial proposal

Revise your original proposal, including three or more possible projects ranked from your favorite ideas to your least favorites. Be specific.

3. November 30 - 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. 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.


GRADE COMPUTATION

ASSIGNMENT WEIGHTS

        1% - GOLum Team Development
        1% - GOLum Team initial proposal
        5% - GOLum 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. 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.

Gordon College policy states that 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.

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 25NO LAB ---
Aug 261.1-7Carbon, bonds & charge

Homework (after class):
Textbook: 1.3, 1.11
Aug 291.9-11
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
Aug30/Sep 11, 2, Lab notebook handout
FW calculator

Collected Homework:
Organic Calculations
Due in two weeks
Lab Orientation, Checkin,
Honing Observational Skills by Candlelight
handout
Aug 311.12-14, 2.5-9Structure vs. behavior: Introduction to functional groups

Homework (after class):
Textbook: 1.22, 1.35
Sep 22.10-12
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 5---NO CLASS TODAY
Labor Day
Sep 6/83,12, handout Melting Point Determination and Significance
Candle Lab
Sep 72.13,14GOLum Milestone #1 due
Relationships Between Physical Properties
and Molecular Structure

Homework (after class):
Physical properties:
2.25, 2.27, 2.38, 2.46
Sep 93.1-6,12-15Acids and bases in organic chemistry

Homework (after class):
Textbook: 3.1, 3.2, 3.9, 3.18, 3.20
Sep 12---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 13/154, 18, 19 (class 1),
handout #1
handout #2
Simple Distillation
Boiling Point Determination
Laboratory Calculations - Due in class Monday
Sep 14---GOLum Beginnings
Green Chemistry lecture by Dr. John Warner video
Only available on Gordon College campus network

GOLum Brainstorming
Sep 164.1-7GOLum Milestone #2 due
Lab calculations sheet due
Alkanes: Nomenclature and Properties

Homework (after class):
4.1 4.2, 4.5a
Sep 19---Nomenclature continued

Homework (after class):
4.6 4.7a, 4.8, 4.23 (skip parts l, m & n), 4.28
Sep 20/22 4, 18, 19 (class 3),
Distillation handout
Fractional Distillation
Sep 21---Nomenclature, concluded; Restrosynthetic concepts
Sep 234.15-17, 7.15Synthesis 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)
Sep 264.8-10Conformational analysis of linear alkanes; Ring strain

Homework (after class):
4.13, 4.38 (these will require a little reading beyond our lecture today)
Sep 27/2930, 33 handout #1
handout #2,
Solomons 2.16  
1. Gas Chromatography of Distillate Fractions
2. Infrared spectroscopy of purified fractions
Sep 284.11-13Conformational 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!
Sep 30---Preparation for Opportunity #1
Oct 34.12-13Special Event - Distinguished Green Chemistry Lecture (Jenks 237, 4:30PM)
Conformational analysis of cyclohexanes

Homework (after class):
Prepare for Op#1
Oct 4NO LAB ---
Oct 5---* * * OPPORTUNITY #1 * * *
Oct 66, 9, 11, 13, 17, 18,
handout
Synthesis and purification of an organic solid
Oct 75.1-6Stereochemistry: Chirality

Homework (after class):
5.1, 5.4, 5.5, 5.6
Oct 105.7Stereochemistry: Nomenclature

Homework (after class):
5.9, 5.11, 5.12, 5.22, 5.36
Oct 116, 9, 11, 13, 17, 18,
handout
Synthesis and purification of an organic solid
Oct 125.8-11Stereochemistry: Optical activity

Homework (after class):
5.15, 5.40abcdefgmnopq, 5.52 (best problem ever!)
Oct 13NO LAB Quad break
Oct 14---No class, quad break
Oct 175.12-14,16NATIONAL CHEMISTRY WEEK!
Reaction types: Addition/Elimination/Substitution/Rearrangement

Homework (after class):
HW problems - click here for solutions
Oct 18/20---LAB: Microwave synthesis of an ionic liquid, [HMIM][Cl]
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.

Use of the CEM Discover Microwave Reactor
Oct 19---Mechanism: SN2 Nucleophilic Substitution

Homework (after class):
TBA
Oct 216.1-4, 14MOLE DAY Celebrated ... (Almost) The most chemical day of the year!
Mechanism: SN1 Nucleophilic Substitution

Homework (after class):
6.3, 6.23
Oct 246.5-8Competition: The SN2 vs. SN1 mechanism

Homework (after class):
TBA
Oct 25/2719 (class 3),
traditional
Revised version
Greener Dehydration of 2-Methylcyclohexanol
Oct 266.9-12Competition: 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
Oct 286.13Competition between types: Substitution vs. Elimination

Homework (after class):
TBA
Oct 316.15-19Final thoughts from chapter 6; Introducing chapter 7

Homework (after class):
TBA
Nov 1NO LAB ---
Nov 2---* * * OPPORTUNITY #2 * * *
Nov 3---GC analysis of alkene products
Nov 47.1-4Alkenes and alkynes: Nomenclature and stability

Homework (after class):
Prepare for Op#2
Nov 77.5-8Alkene synthesis: Zaitsev's rule; Olefin metathesis

Homework (after class):
TBA
Nov 8NO LAB Day Of Prayer
Nov 97.9-11E2 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 10web resourceThe Dose Makes the Poison: Comparative ecotoxicity: Set up test plates
Nov 11---GOLum Team Lunch
Meet with your team to discuss goals for end of semester/td>
Nov 147.12-14Alkyne synthesis
Hydrogenation revisited

Homework (after class):
TBA
Nov 15Lab #1 - web resource
Lab #2 - GC
1. The Dose Makes the Poison: Comparative ecotoxicity: Set up test plates
2. GC analysis of alkene products
Nov 168.1-4Alkenes 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 17web resourceThe Dose Makes the Poison: Comparative ecotoxicity: Collect results
Nov 188.5-10Oxymercuration/demercuration
Organoborane chemistry

Homework (after class):
TBA
Nov 218.11-13Alkene halogenation

Homework (after class):
TBA
Nov 22web resourceThe Dose Makes the Poison: Comparative ecotoxicity: Collect results
Nov 23---No class, Prepare for Thanksgiving
Nov 24---Be THANKFUL
Nov 25---No class, Recuperate from Thanksgiving
Nov 288.14-16Alkene reactions with carbene; Oxidation

Homework (after class):
TBA
Nov 29/Dec 1handout Preparation of an alkyne: Diphenylacetylene
Nov 308.17-20GOLum Milestone #3 due
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 210.1-3,6Radical Reactions

Homework (after class):
TBA
Dec 510.4,5,7,10,11Radical Reactions

Homework (after class):
10.1, 10.6, 10.7, 10.16, 10.19, 10.20, 10.29abcef
Dec 6/8--- Laboratory Exam; Check-out
Dec 7---Review and Loose ends
Dec 12Monday
9:00AM - 11:00AM
* * * OPPORTUNITY #3 * * *