ORGANIC CHEMISTRY II
Chemistry 212
Gordon College, Spring 2014


Prof. Irvin J. Levy
Office Hours:
MWF, 9:00-10:15, 12:30-1:30 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, 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 listed below. Make-ups will be given only under extreme circumstances (illness, serious personal difficulty).

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 17 - 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 24 - Team Report

In this milestone you will report the following:

3. February 10 - 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 28 - 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 1512.1-3 (skip 12.3D)Syllabus
Quickstart assigned
Introduction to Organic redox reactions
Reductions: Alcohols from carbonyl compounds.
Jan 1712.4 (skip 12.4AB)

Homework:
12.3, 12.5abcd, 12.14, 12.17,
12.18abde, 12.19, 12.25
Oxidations: Synthesis of carbonyl compounds.
Milestone #1 due
Jan 20---Martin Luther King Holiday
LAB Jan 21handoutSodium borohydride reduction of a ketone: Preparation of meso-hydrobenzoin
Jan 2212.5-8The Grignard Reaction
Jan 24---

Homework:
Take home quiz distributed
chapter concluded
Milestone #2 due; Team Report
one per team, emailed to green-chem@gordon.edu
Jan 27---

GUEST SPEAKER #1 - Dr. Joshua Martin - KOS 104 - 11:25 am
optional GUEST SPEAKER #2 - Dr. David Tyler - KOS 124 - 4:30 pm
LAB Jan 28Quickstart Completion Day - No Laboratory today
Jan 29

13.1-4

Homework:
13.2, 13.3, 13.4, 13.5
Take home Quiz collected

Conjugated Unsaturated Systems
The Game of Resonance
Jan 31---

GUEST SPEAKER - Dr. Michael Paul - KOS 104 - 11:25 am
Feb 3

13.5-7, 13.9

Homework:
13.6, 13.9, 13.13, 13.14
13.32, 13.33
Conjugated Unsaturated Systems: Conjugated Dienes

Quickstart draft #1 due today

optional GUEST SPEAKER - Ms. Otonye Braide - KOS 124 - 4:30 PM
LAB Feb 4handoutSelective Oxidation of Benzyl Alcohol
Feb 513.9,10

Homework:
13.14, 13.15, 13.16, 13.39
13.40, 13.43
Dienes and the Diels-Alder Reaction

optional GUEST SPEAKER - Dr. Mary Devadas - KOS 124 - 4:30 PM
Feb 714.1-4

Homework:
14.1, 14.16abcdefghjkmnpqr
Aromaticity, Introduced
Feb 1014.5, 14.6AAromaticity, Chemical definition

Milestone #3 due; Annotated Bibliography & Revised Team Report
one per team, emailed to green-chem@gordon.edu
LAB Feb 11handoutAqueous Diels-Alder Reaction
Feb 1214.7B, 14.7D, 14.8-14.10

Homework:
14.12, 14.18, 14.21, 14.22
Aromaticity, Hückel's Rules
Feb 1415.1-5

Homework:
Review reading section 14.2
Problems 15.1, Take-Home Quiz (due Monday)
Reactions of aromatic compounds, Introduction
Electrophilic Aromatic Substitution: Halogenation, Nitration,
Sulfonation, Desulfonation
Feb 1715.6-10

Homework:
15.3, 15.4, 15.5abc, 15.22c
Reactions of aromatic compounds: Alkylation & Acylation

optional GUEST SPEAKER - Stephanie Skiles - KOS 124 - 4:30 PM
LAB Feb 18handoutSynthesis of Iodovanillin
Feb 1915.10Reactions of aromatic compounds: Polysubstitution
Feb 21---* * * OPPORTUNITY #1 * * *
Feb 2415.11,13

Homework:
15.8, 15.28, 15.29, 15.30
Reactions of aromatic compounds, continued
LAB Feb 25---Reactions of aromatic compounds, continued
Feb 2615.14-15

Homework:
15.31abcefg, 15.38, 15.51
Reactions of aromatic compounds, continued
Feb 2816Aldehydes and ketones I.
Nucleophilic addition to the carbonyl group
Mar 316
Homework:
16.3, 16.4abcd, 16.5, 16.5, 16.12, 16.22abdej
Aldehydes and ketones I.
Nucleophilic addition to the carbonyl group, continued
LAB Mar 4Project ideasSynthesis Team Projects
Introduction and First Steps
Mar 516Wolff-Kishner Reduction, Link 1, Link 2
---Spring Break, March 6 - 16
Mar 17No lecture
GOLum Work Time
LAB Mar 18Solomons 9.1-9.4, 9.6-9.9C, 9.9E
Practice problems:
9.1, 9,2, 9.4, 9.6, 9.9, 9.10, 9.25,
9.38 (great practice!)
NMR video
DUE ON FRIDAY: Link
Mar 19No lecture
GOLum Work Time
Mar 2117Carboxylic acids and their derivatives
Mar 2417
Homework:
17.1abcd, 17.3, 17.4abdhi, 17.5, 17.6,
17.18abcd, 17.21
continued
LAB Mar 25---Team Projects Begin
Mar 2617continued
Mar 2817concluded
Mar 31---
* * * OPPORTUNITY #2 * * *
LAB Apr 1---Continue Team Projects
Apr 218

Enolate Chemistry, Part 1
Apr 418

continued
Apr 7Reading:
18.1 - 18.3C, 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
concluded
LAB Apr 8---Continue Team Projects
Apr 919Enolate Chemistry, Part 2
Apr 1119continued
Apr 14No lecture
GOLum Work Time
Annual Green Chemistry Lecture
Dr. David Constable, KOS 104, 4:30-5:30 pm
LAB Apr 15---Continue Team Projects
Apr 1619concluded
Apr 18---Easter Break
Apr 21---Easter Break
LAB Apr 22
Earth Day!
---Conclude Team Projects
Apr 2320Amines
Apr 25

20

continued
Apr 2820concluded
Milestone #6. GOLum binder is due
LAB Apr 29---Lab Exam
Check-out
Preparation for poster presentation
Apr 3021Phenols and Aryl Halides
May 2---* * * OPPORTUNITY #3 * * *
May 521continued
May 6Thursday schedule, No Organic Lab
May 7

---Conclusion, Discussion of final
URS 2014; Poster day for Synthesis Teams
Friday, May 9
2:30 - 4:30 PM
---

* * * FINAL EXAMINATION * * *