ORGANIC CHEMISTRY II
Chemistry 212
Gordon College, Spring 2010


Prof. Irvin J. Levy
Office Hours:
MWF, 8:00-9:00am, 12:30-1:00pm
T, 8:00-9:30am; or by appointment
It's good to be green!
- K.

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.

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

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 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 20 - Team Report

In this milestone you will report the following:

2. February 17 - Revised Annotated Bibliography & Revised Team Report

You prepared an annotated bibliography last semester. You are to revise it by adding all new resources that you have discovered and by deleting resources that were on the original bibliography that you no longer believe are useful. Remember that you should include a descriptive entry for every web site, article, book, handout, and 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.

3. 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 greenchemistry@comcast.net. In order to receive credit, the written critique must be submitted within seven (7) days of the peer review.

4. April 21 - 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)

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

PRACTICE EXAMINATIONS (EXTERNAL WEBSITES)




Tentative Class Schedule


Meeting(s)  Chapter  Topic
Jan 1311.1-6,10Alcohols: Reactions involving the O-H bond
Quickstart assigned
Jan 1511.7-9,11,13Alcohols: Reactions involving the R-O bond
Jan 18---NO CLASSES - MARTIN LUTHER KING DAY
LAB Jan 19handoutSodium borohydride reduction of a ketone: Preparation of meso-hydrobenzoin
Jan 2011.12,14,15,17Ether reactions
GOLum Milestone Due--Team Report
Jan 2212.1-3Introduction to Organic redox reactions
Reductions: Alcohols from carbonyl compounds.
Jan 2512.4

Oxidations: Synthesis of carbonyl compounds.
LAB Jan 26handoutSelective Oxidation of Benzyl Alcohol
Jan 27

12.5-8The Grignard Reaction
Milestone #1 due
Jan 29---concluded
Feb 113.1-5Conjugated Unsaturated Systems
The Game of Resonance
LAB Feb 2handoutGrignard Reaction: Preparation of Triphenylmethanol
Feb 3---continued
Feb 5---continued
Feb 813.6-11Dienes and the Diels-Alder Reaction
LAB Feb 9handoutAqueous Diels-Alder Reaction
Feb 10---continued
Feb 1214Aromaticity
Feb 15---concluded
LAB Feb 16handoutSynthesis of Iodovanillin
Feb 1715Reactions of aromatic compounds
GOLum Milestone due-Revised Annotated Bibliography & Revised Team Report
Feb 19---* * * OPPORTUNITY #1 * * *
Feb 22---continued
LAB Feb 23---EAS continued
Feb 24---continued
Feb 26---continued
Milestone #3 due
Mar 1---continued
LAB Mar 2J. Chem. Educ. articleMicrowave-Assisted Synthesis of a Natural Insecticide
Mar 3---concluded, at last!
------Spring Break
Mar 15

16

Aldehydes and ketones I.
Nucleophilic addition to the carbonyl group
LAB Mar 16---Synthesis Team Projects
Mar 17---Wolff-Kishner Reduction, Link 1, Link 2
Mar 19---Olefin Methathesis, Link 1, Link 2
* * * OPPORTUNITY #2 AVAILABLE * * *
Mar 22---No lecture
GOLum Work Time
LAB Mar 23Solomons 9.1-9.11C
(skip 9.5, 9.9D)
Practice problems:
9.28
NMR video
DUE ON FRIDAY AS PART OF OPPORTUNITY #2: Link
Mar 24---No lecture
GOLum Work Time
Mar 26

---concluded
* * * OPPORTUNITY #2 COLLECTED * * *
Mar 2917

Aldehydes and ketones II.
Enolate reactions
LAB Mar 30---Continue Team Projects
Mar 31---

continued
Apr 2---concluded
Apr 5

18

Carboxylic acids and their derivatives
Nucleophilic addition-elimination at the acyl carbon
LAB Apr 6---Continue Team Projects
Apr 7---continued
Apr 9---Easter Break
Apr 12---Easter Break
LAB Apr 13---Conclude Team Projects
Apr 14

18

continued
Apr 16

---concluded
Apr 1919Synthesis and reactions of β-dicarbonyl compounds
LAB Apr 20handoutBiginelli Reaction
Apr 21---concluded
GOLum Binder Is Due!
Apr 2320Amines
Apr 26---* * * OPPORTUNITY #3 * * *
LAB Apr 27---Lab Exam/Check-out
Apr 2821

Amines, concluded
Apr 30---Phenols and aryl halides
Nucleophilic aryl substitution
May 3---continued
May 4---Thursday schedule, No Organic Lab
May 5

---Conclusion, Prep for final
Poster day for Synthesis Teams
Monday, May 10
2:00 pm - 4:00 pm
---

* * * FINAL EXAMINATION * * *