ORGANIC CHEMISTRY II
Chemistry 213
Salem State College, Summer 2003


Prof. Irvin J. Levy
Lecture:
MWF, 9:00am-12:00pm
Laboratory:
T/Th, 9:00am-12:30pm
There is excitement, adventure and challenge and there can be great art in organic synthesis.
- R.B. Woodward

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. This second semester course assumes a working knowledge of the material from the first semester of the course. For reference, the syllabus from the first course is available online.

TEXTS

1. Organic Chemistry, 7th ed. upgrade, Graham Solomons & Craig Fryhle
2. The Organic Chem Lab Survival Manual, 5th ed., Zubrick
(Recommended) Study Guide to Organic Chemistry,7th ed. upgrade, Solomons & Fryhle

ADDITIONAL MATERIALS

1. Bound notebook for laboratory
2. Safety goggles as required by Department
3. Protective gloves

COURSE STRUCTURE

Daily effort through reading and problem solving is essential to success in this course. Specific 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 not be collected; however, in order to provide continuing motivation, each lecture will begin with a brief quiz based upon the previous assignment. Self-evaluation of homework will be possible through the use of the Study Guide.

CRITERIA FOR EVALUATION

Two Opportunities will be offered on the dates listed in the enclosed Class Schedule. Make-up opportunities are not available. Two low quiz scores will be dropped when computing the final quiz grade. Make-up quizzes are not available.

Laboratories during the second semester use the techniques introduced during the first semester to develop continued depth of skill in the chemistry laboratory. In particular it is assumed that students are familiar with the use of ground glass chemical apparatus, melting point determination, recrystallization, decolorization, vacuum filtration, simple distillation, fractional distillation, extraction, drying, evaporation, and gas chromatography. Students will be challenged to think critically about their work and to take significant responsibility for planning their use of time in the lab.

Laboratory work will be assessed in the following way. A student is expected to attend all labs (or make-up 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 attendance be very faithful. The lab grade 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 critiqued by self-evaluation, peer-evaluation (neither of which will affect the lab grade) and discussion with the professor which will affect the lab grade. Additionally, during the last laboratory session, a laboratory exam will be administered. The lab grade will be determined as follows:

          0% - Self-evaluation, Peer-evaluation
          67% - Professor's evaluation
          33% - Laboratory examination

Overall grades will be computed as follows:


          20% - Opportunity #1
          20% - Opportunity #2 (ACS standardized final examination)
          35% - Quizzes (drop 2 low scores)
          25% - Laboratory

Both lecture and laboratory must have passing grades in order for a passing grade in the course.

Please note: The summer course in organic chemistry is an accelerated class which covers the same material as the normal fall/spring curriculum. This class is an equivalent time commitment to a full-time job. Between lecture, laboratory, reading and homework problems you should plan to spend about 40 hours per week working on this class. If you are not able to make this significant time commitment your final result is likely to be very poor. Please make time to allow for success.

IMPORTANT! The grade assigned at the end of the course is based solely on performance on graded work during the semester. There is no element of the grade which depends on what a student "needs" to receive in the class. Sorry to include something that should be obvious. Believe me, from past experience, it's necessary.



RESOURCES

ChemSketch: All-Purpose Chemical Drawing and Graphics Softwaredownload
IUPAC Naming Tooldownload
Laboratory Notebook Guidelineshandout
Calculating limiting reagents and percentage yieldhandout
IUPAC Rules of Nomenclaturewebsite
Aldrich Chemical Company Search Pagewebsite
ChemExper Chemical Directorywebsite
Acros Chemicalswebsite
NIST Chemistry Webbookwebsite

Tentative Class Schedule


Date   Chapter  Topic

M, June 2311Alcohols and Ethers
W, June 25

12

Oxidation & Reduction of Carbonyl Compounds
The Grignard Reaction
F, June 2713Resonance - Conjugation - Delocalization - Stability

M, June 3014Aromaticity
W, July 215.1-10Reactions of Aromatic Compounds, part 1
Th, July 315.11-15Reactions of Aromatic Compounds, part 2

M, July 7

---
16.1-6
* * * OPPORTUNITY #1 * * *
After Opportunity: Aldehydes and Ketones: Synthesis; Nucleophilic addition
W, July 916.7,8,10-14Aldehydes and ketones: Wittig reaction; Ammonia addition compounds
F, July 1117.1-4Enolate Chemistry: Introduction to aldol reaction

M, July 1417.5-7,9Enolate Chemistry: Modifications to the simple aldol reaction
W, July 1618Carboxylic acids and their derivatives, part 1
F, July 18

18,19

Carboxylic acids and their derivatives, part 2
Acetoacetic ester synthesis; Malonic estersynthesis

M, July 21

20.1-8,13
21
Amines (selected topics)
Phenols; Nucleophilic Aromatic Substitution
W, July 23---Catch-up; Directed Study Session
F, July 25--- * * * OPPORTUNITY #2 * * *



Tentative Lab Schedule


Note: Laboratory is preceeded by a mandatory pre-lab lecture. Chapters below refer to reading required from "The Organic Chem Lab Survival Manual" before arriving on the lab day. All handouts must be read before arriving on the lab day. Unannounced lab quizzes may be administered. These quizzes will be graded on a Pass/Fail basis. Passing scores will not affect the final lab grade. Each failing score will reduce the final lab grade by 1/3 of a letter grade.

Meeting  Chapter  Topic

June 24


handout
ALL NEW
students
New Students ONLY:
Introduction to Organic Laboratory
Check-in to lockers
June 26


handout
pp. 61-62,
ch. 9, 10, 22, 23
Grignard synthesis of triphenylmethanol



July 1

handout

Diels-Alder preparation of
endo-norbornene-5,6-dicarboxylic anhydride

July 8handoutPreparation of p-nitroaniline
July 10handoutPurification of p-nitroaniline

July 15handout #1Preparation of soap: Large-scale organic synthesis
handout #2Photochemical preparation of benzopinacol
July 17handoutClaisen-Schmidt condensation of dibenzalacetone

July 22handoutTBA - Stay tuned!
July 24---Laboratory Exam, Check-Out