ORGANIC CHEMISTRY II
Chemistry 212
Gordon College, Spring 2013


Prof. Irvin J. Levy
Office Hours:
MWF, 12:30 - 2:00 PM
T, 12:45-1:15 PM; or by appointment

This continuation of 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 based molecules. Thorough knowledge of the material from the first semester of the course is an assumed prerequisite (syllabus for that course is found here).

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, 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

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 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 significant amount of time on the week of April 8 to April 12. 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. 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
      15% - Quizzes (drop three low scores)
      25% - Laboratory (includes lab exam)
      20% - GOLum
      10% - Final examination (curved)

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

1. January 18 - Group Meeting w/Professor

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.

2. January 25 - Team Report

In this milestone you will report the following:

3. February 11 - Annotated Bibliography & Revised Team Report

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.

4. March/April - Peer Support

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.

5. April 29 - Project completed and submitted in a binder with all relevant materials (Note: this one due date is negotiable, for good cause, if approved in writing at least one week in advance)

Your team will submit a white 1" binder containing the following:
CD with relevant documents, handouts, photos, and copy of all of the following materials1 CD

Name of project and team members
Brief bio statements (with photos) and abstract
1 page maximum

Description of the audienceabout 1 page
Description of the presentation forumabout 1 page
Mirror: Copies of all material presented for the audiencevariable, 5-15 pages
Final annotated bibliographyvariable, 1-10 pages
Final action plan1-2 pages
Written critiques from peers1-3 pages
Your own critique, analysis of outcomes, suggestions for future work1-2 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:

  1. 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.)
  2. Meet with an Academic Support Center (ASC) staff person to discuss the accommodations for which you are eligible and the procedures for obtaining them.
  3. Obtain a Faculty Notification Form from the ASC and deliver it your professor within the first full week of the semester.
  4. 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




Tentative Class Schedule


Meeting(s)  Chapter  Topic
Jan 1612.1-3Syllabus
Quickstart assigned
Introduction to Organic redox reactions
Reductions: Alcohols from carbonyl compounds.
Jan 18---GOLum group team meetings
Milestone #1; Group Meeting
as scheduled in previous class
Jan 21---Martin Luther King Holiday
LAB Jan 22handoutSodium borohydride reduction of a ketone: Preparation of meso-hydrobenzoin
Jan 2312.4Oxidations: Synthesis of carbonyl compounds.
Jan 2512.5-8The Grignard Reaction
Milestone #2 due; Team Report
one per team, emailed to green-chem@gordon.edu
Jan 28---

chapter concluded
LAB Jan 29handoutSelective Oxidation of Benzyl Alcohol
Jan 30

13.1-5Conjugated Unsaturated Systems
The Game of Resonance
Feb 1---continued
Feb 4---continued
LAB Feb 5handoutGrignard Reaction: Preparation of Triphenylmethanol
Feb 613.6-11Dienes and the Diels-Alder Reaction
Feb 8---continued
Feb 1114Aromaticity
Milestone #3 due; Annotated Bibliography & Revised Team Report
one per team, emailed to green-chem@gordon.edu
LAB Feb 12handoutAqueous Diels-Alder Reaction
Feb 13---concluded
Feb 1515Reactions of aromatic compounds
Feb 18---continued
LAB Feb 19handoutSynthesis of Iodovanillin
Feb 20--continued
Feb 22---* * * OPPORTUNITY #1 * * *
Feb 2515EAS, continued
LAB Feb 26---continued
Feb 27, LEAP DAY---continued
Mar 115EAS, concluded, at last!
Mar 416Aldehydes and ketones I.
Nucleophilic addition to the carbonyl group
LAB Mar 5Synthesis of a quinoxalineHeterocyclic amines via imine formation
Mar 6---Wolff-Kishner Reduction, Link 1, Link 2
------Spring Break
Mar 18

---

Olefin Methathesis, Link 1, Link 2
LAB Mar 19---Synthesis Team Projects
Introduction and First Steps
Mar 2017Carboxylic acids and their derivatives
Mar 22---continued
Mar 2517

continued
LAB Mar 26---Continue Team Projects
Mar 27---

concluded
Mar 29---Easter Break
Apr 1---Easter Break
LAB Apr 2---Continue Team Projects
Apr 318Enolate chemistry, Part I
Apr 5

--

concluded
Opportunity #2 Distributed
Apr 8---No lecture
GOLum Work Time
LAB Apr 9Solomons 9.1-9.11C
(skip 9.5, 9.9D)
Practice problems:
9.28
NMR video
DUE ON FRIDAY AS PART OF OPPORTUNITY #2: Link
Apr 10---No lecture
GOLum Work Time
Apr 12

---concluded
* * * OPPORTUNITY #2 COLLECTED * * *
Apr 1519Enolate chemistry, Part II
LAB Apr 16---Continue Team Projects
Apr 17

--

continued
Apr 19

---concluded
Apr 2220Amines
LAB Apr 23---Conclude Team Projects
Apr 24---concluded
Apr 2621Phenols and aryl halides
Nucleophilic aryl substitution
Apr 2921

concluded
Milestone #6. GOLum binder is due
LAB Apr 30---Lab Exam
Check-out
Preparation for poster presentation
May 1---* * * OPPORTUNITY #3 * * *
May 3---TBA: Special Topics
May 6---Research Poster Peer Presentation
May 7---Thursday schedule, No Organic Lab
May 8

---Conclusion, Discussion of final
URS 2013; Poster day for Synthesis Teams
Friday, May 10
2:30 - 4:30 PM
---

* * * FINAL EXAMINATION * * *