1. Organic Chemistry, 11th ed., Graham Solomons & Craig Fryhle
2. The Organic Chem Lab Survival Manual, 9th ed., Zubrick
(Recommended) Study Guide to Organic Chemistry, 11th ed., Solomons & Fryhle
| Prof. Irvin J. Levy Office Hours: MWF, 12:30-2:00 PM Th, 10:00-noon or by appointment |
This semester we will expand our intitial understanding of green chemistry by producing outreach projects to enhance green chemistry literacy for others.
TEXTS
1. Organic Chemistry, 11th ed., Graham Solomons & Craig Fryhle
2. The Organic Chem Lab Survival Manual, 9th ed., Zubrick
(Recommended) Study Guide to Organic Chemistry, 11th 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 service-learning 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. Due to the complexity of this project, several intermediate milestones are due (sse below). Failure to observe these due dates will result in a one-half letter grade reduction in the final project grade for each milestone missed.
Three Opportunities will be administered on the dates
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. The study guide for this examination is available for purchase
from the ACS at this link.
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 unless otherwise indciated. Final grades will be computed as follows:
30% - Three Opportunities
GREEN ORGANIC LITERACY FORUM (GOLum) ASSIGNMENT
Last semester was a time to gather with a team and develop a plan for a GOLum project. This semester you will bring your project to
completion. Several important dates apply to the various milestones in the 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 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
In this milestone all of the members of your team will gather with the professor to brainstorm
about the project, find intial resources, and clarify the goals. Every member of the team must
attend this 15-20 minute meeting which will be scheduled in advance.
In this milestone you will report the following:
Based on the purpose of your project, you need to develop specific expertise in green chemistry as well as having general
knowledge of the topic. In this assignment you are to compile resources (books, articles, web resources, people, etc.) that can be used
to support your outreach and to provide your "training" as you prepare to reach out. Include
a descriptive entry for every web site, article, book, handout, or person (other than your team members or your professor) that is
relevant to your project.
You are to resubmit your Team Report (from the previous milestone) noting what tasks have been accomplished and altering the timeline
as needed. Add a paragraph that clearly states change in the report from the previous version and the reason for those changes.
During the months of March and April, projects will be nearing completion. Teams will need peer support to complete their projects. For
example, if students produce a video, they will need others to critique their script or raw footage; if students produce written materials,
they will need others to critique their written work; if students prepare new lab activities, they will need others to test their activities;
if students are visiting a high school, they will need an audience on our campus to run a "dress rehearsal".
Each student in the class will be required to perform three (3) critiques in support of their peers. In order for a critique to count, the student must
first confirm (verbally) with the professor that the critique is permitted (for example, I can't have 20 people critique the same video!). Unless otherwise
directed, credit is received when the student sends a WRITTEN critique to all members of the team along with a copy to green-chem@gordon.edu. In order to
receive credit, the written critique must be submitted within seven (7) days of the peer review.
Your team will submit a white 1" binder containing the following:
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.
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.
15% - Quizzes (drop three low scores)
25% - Laboratory (includes lab exam)
20% - GOLum
10% - Final examination (curved)
CD with relevant documents, handouts, photos, and copy of all of the following materials 1 CD Name of project and team members
Brief bio statements (with photos) and abstract1 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 Final annotated bibliography variable, 1-10 pages Final action plan 1-2 pages Written critiques from peers 1-3 pages Your own critique, analysis of outcomes, suggestions for future work 1-2 pages
Students with disabilities who may need academic accommodations
should follow this procedure:
Jan 14 12.1-3 (skip 12.3D) Introduction to organic redox reactions
Reductions: Alcohols from carbonyl compounds
Homework:
Syllabus
Quickstart assigned
Jan 16 12.4 (skip 12.4AB) Oxidations: Synthesis of carbonyl compounds.
Homework:
12.3, 12.5abcd, 12.14, 12.17, 12.18abde, 12.19, 12.25
---------------------
Jan 19 Martin Luther King Holiday
I Have A Dream speech
LAB, Jan 20 Sodium borohydride reduction of a ketone: Preparation of meso-hydrobenzoin
handout
Jan 21 12.5-8 The Grignard Reaction
Jan 23 Chapter concluded
--- MILESTONE #1 ---
Homework:
Take home quiz distributed - Synthetic Interlude
---------------------
Jan 26 13.1-4 Conjugated Unsaturated Systems
The Game of Resonance
--- Take Home Quiz Collected ---
Homework:
13.2, 13.3, 13.4, 13.5
LAB, Jan 27 Selective Oxidation of Benzyl Alcohol
handout
Jan 28 13.5-7, 13.9 Conjugated Unsaturated Systems: Conjugated Dienes
--- Quickstart draft #1 due today ---
--- MILESTONE #2 ---
Team Report, one per team, emailed to green-chem@gordon.edu
Homework:
13.6, 13.9, 13.13, 13.14, 13.32, 13.33
Jan 30 13.9-10 Dienes and the Diels-Alder Reaction
Homework:
13.14, 13.15, 13.16, 13.39, 13.40, 13.43
---------------------
Feb 2 14.1-4 Aromaticity, introduced
Homework:
14.1, 14.16abcdefghjkmnpqr
LAB, Feb 3 Aqueous Diels-Alder Reaction
Check email for handout
Feb 4 14.5, 14.6A Aromaticity, Chemical definition
Feb 6 14.7B, 14.7D, Aromaticity, Hückel's Rules
14.8-14.10
Homework:
14.12, 14.18, 14.21, 14.22
Take-Home Quiz (due next Wednesday)
---------------------
Feb 9 GOLum Work Day No lecture - meet with team to prepare for
next Milestone
LAB, Feb 10 TBA
Feb 11 15.1-5 Reactions of aromatic compounds, Introduction
Electrophilic Aromatic Substitution:
Halogenation, Nitration, Sulfonation, Desulfonation
--- Take Home Quiz collected ---
--- MILESTONE #3 ---
Annotated Bibliography & Revised Team Report
one per team, emailed to green-chem@gordon.edu<
Homework:
15.1
Feb 13 15.6-10 Reactions of aromatic compounds: Alkylation & Acylation
Homework:
15.3, 15.4, 15.5abc, 15.22c
---------------------
Feb 16 --- Catch-up for Op #1
LAB, Feb 17 Synthesis of Iodovanillin, begins
Check email for handout
Feb 18 --- * * * OPPORTUNITY #1 * * *
Feb 20 15.10 Reactions of aromatic compounds: Polysubstitution
---------------------
Feb 23 15.11,13 Reactions of aromatic compounds, continued
Homework:
15.8, 15.28, 15.29, 15.30
LAB, Feb 24 Synthesis of Iodovanillin, continues
Feb 25 15.14-15 Reactions of aromatic compounds, continued
Homework:
15.31abcefg, 15.38, 15.51
Feb 27 16 Aldehydes and ketones I.
Nucleophilic addition to the carbonyl group
---------------------
Mar 2 16 continued...
Homework:
16.3, 16.4abcd, 16.5, 16.5, 16.12, 16.22abdej
LAB, Mar 3 Synthesis Team Projects
Introduction and First Steps
Project ideas
Mar 4 16 concluded...
Wolff-Kishner Reduction, Link 1
Link 2
---------------------
!!! Spring Break !!!
---------------------
Mar 16 17 Carboxylic acids and their derivatives
LAB, Mar 17 Team Projects Begin
Mar 18 17 continued...
Homework:
17.1abcd, 17.3, 17.4abdhi, 17.5, 17.6, 17.18abcd, 17.21
Mar 20 17 continued...
--- OPPORTUNITY #2 Distributed ----
(Take-Home)
---------------------
Mar 23 No lecture
GOLum Work Time
LAB, Mar 24 NMR Video
Reading and Homework:
Solomons 9.1-9.4, 9.6-9.9C, 9.9E
9.1, 9,2, 9.4, 9.6, 9.9, 9.10, 9.25, 9.38 (great practice!)
NMR Homework - Due as separate portion of Op#2
Mar 25 No lecture
GOLum Work Time
Mar 27 17 continued...
* * * OPPORTUNITY #2 Collected * * *
---------------------
Mar 30 17 concluded.
LAB, Mar 31 Continue Team Projects
Apr 1 18 Enolate Chemistry, Part 1
Apr 3 --- Easter Break
---------------------
Apr 6 --- Easter Break
LAB, Apr 7 Continue Team Projects
Apr 8 18.1 - 18.3C, concluded
18.5 - 18.8,
18.10 (except rxn 9)
Homework:
18.7, 18.8, 18.9, 18.12, 18.15, 18.19b,
18.21, 18.33a, 18.33b
Apr 10 19 Enolate Chemistry, Part 2
---------------------
Apr 13 19 concluded
LAB, Apr 14 Continue Team Projects
Apr 15 20 Amines
Apr 17 --- No lecture today.
GOLum group meeting - Assign final binder tasks
---------------------
Apr 20 20 concluded
LAB, Apr 21 Continue Team Projects
Preparation for poster presentation
Apr 22 21 Phenols and Aryl Halides
--- HAPPY Earth Day! ---
Apr 24 21 concluded
---------------------
Apr 27 --- --- MILESTONE #6 ---
GOLum Binders Due, Summary Reports to Class
LAB, Apr 28 --- Lab Exam (oral)
Check-out
Apr 29 TBA Special Topics (Radical reactions, etc)
May 1 --- * * * OPPORTUNITY #3 * * *
---------------------
May 4 --- Research posters - Share with class before posting
May 5 --- Thursday schedule - No lab
Extended office hours
May 6 Conclusion
Discussion of final
Friday, May 8, 2:30 - 4:30 PM * * * FINAL EXAMINATION * * *