Chemistry 212
Gordon College, Summer 2013

Irvin J. Levy,
Professor of Chemistry
Katy van Kirk,
Laboratory Instructor
M-Th, 6:00pm-10:00pm
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. We will seek to do this in ways that are consisent with the principles of green chemistry.

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.


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


1. Bound notebook for laboratory
2. Safety goggles as required by Department
3. Protective gloves
(Recommended) Darling Flexible Stereochemical Models


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.


Two Opportunities will be offered on the dates listed in the enclosed Class Schedule. Opportunity #2 is the American Chemical Society's examination for Organic Chemistry. Students who perform at the 90th percentile or higher on this exam will receive an automatic grade of A for the course, provided all laboratory work is completed. A 164-page study guide for this exam is available for purchase online.

Two low quiz scores will be dropped when computing the final quiz grade. Make-up quizzes are not available.

Laboratories during the second semester build from the techniques practiced during the first semester. Specifically, students should be familiar with the use of ground glass chemical apparatus, infrared spectroscopy, melting point determination, recrystallization, vacuum filtration, distillation (several types), extraction, drying, and evaporation.

Laboratory grading is partially subjective; you will be evaluated on your general preparedness and effort. Additionally, during the last laboratory session, a laboratory exam will be administered. Details will be provided in the laboratory syllabus on the first evening of lab. The lab grade will be determined as follows:

          33% - Professor's evaluation
          33% - Pre-laboratory quiz
          33% - Laboratory examination

Overall grades will be computed as follows:

          40% - Opportunity #1 and #2
          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. Between lecture, laboratory, reading and homework problems you should plan to spend about 20 hours per week working on this class. Past experience shows that students who have large time commitments outside this class often perform very poorly. 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.


Tentative Class Schedule

For each date below, the assigned reading should be read before coming to class on that day. Occasionally we will spend more (or less) time on a topic than indicated below. Accordingly, variations in the reading schedule may occur as announced in class.

Note: The syllabus for laboratory will be distributed during the first laboratory session. Come equipped with lab notebook, goggles and proper laboratory attire.

Date          Reading assignment            Topic

June 24       chap. 11 skip sections:       Alcohols and Ethers
              11.11CDE, 11.16
              Homework problems: 
              11.3, 11.4, 11.5, 11.6, 
              11.12, 11.19, 11.26ade, 

LAB, June 25  LAB - See lab syllabus

June 26 12.1-8 Oxidation & Reduction of Carbonyl Compounds The Grignard Reaction Homework: 1. When reading, be sure to carefully read 12.8B which we have not discussed 2. Homework problems: 12.3, 12.4, 12.5, 12.7, 12.8, 12.9, 12.26 (good review!), 12.30g

LAB, June 27  LAB - See lab syllabus

July 1 13.1-8,10 Resonance - Conjugation - Delocalization - Stability Diene reactions: Homework problems: o conjugate addtion 13.2, 13.3, 13.4, 13.5, o the Diels-Alder reaction 13.6, 13.9a, 13.11, 13.12, 13.29, 13.40abcde

LAB, July 2   LAB - See lab syllabus        

July 3 14 Aromaticity 15.1-2 Introduction to the reactions of aromatic molecules Homework: 14.1acd, 14.16abcdefghijklmnpqr, 14.21 work on take-home quiz July 4 No class, Celebrate your independence!
July 8 15.3-16 Take-home quiz is due Homework: Reactions of aromatic molecules, continued a. Carefully read 15.11 b. Homework problems: 15.4, 15.7, 15.8, 15.11, 15.16, 15.17, 15.18, 15.31, 15.32 July 9 16.1-16.8,10-14 Aldehydes and Ketones Special Topic G.2 Nomenclature, Synthesis (found between pgs Reactions: Nucleophilic addition 999 and 1000 in text) Ammonia addition compounds Wittig reactions and Greener Alternatives Homework: Link to Nobel Prize site: Grubbs lecture 16.2, 16.3a, 16.4abcde, Metathesis animation 16.13, 16.17abcde, G.9 Metathesis dancers

LAB, July 10  LAB - See lab syllabus

July 11 17 Carboxylic acids and their derivatives Homework problems: 17.1, 17.3, 17.4abdhi, 17.5, 17.6, 17.7b, 17.13ab, 17.18abcdefghijk, 17.22acdefghijkl, 17.28, 17.36 Prepare for Op#1
July 15 *** Opportunity #1 *** Chaps. 11 - 16

              After opportunity:            LAB - See lab syllabus

July 16 18.1-3,5-8,10 Enolate Chemistry - Part I (skip 18.3D) Tautomerization Haloform reaction Active methylene syntheses w/ acetoacetic ester & malonic ester 19.1,2,4-7 Enolate Chemistry - Part II Claisen condensation Aldol reactions Claisen-Schmidt reaction Homework problems: 18.7, 18.8, 18.9, 18.12, 18.15, 18.18adf, 18.21ab, 18.22ab, 18.28 (this is a good problem that reviews a lot!) Chapter 19 - TBA Also, show how an alkyne can be used to prepare a) 2-hexanone and b) pentanal.

LAB, July 17  LAB - See lab syllabus

LAB, July 18  LAB - See lab syllabus

July 22 20.1-7,12 Amines 21 Phenols; Nucleophilic Aromatic Substitution

LAB, July 23  LAB - See lab syllabus

LAB, July 24  LAB - See lab syllabus
              Lab checkout
              Laboratory examination

              Q&A for Opportunity #2
July 25 *** Opportunity #2 *** July 26 Sit back and relax. You made it!