Chemistry 211
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.


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. 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 first semester focus on development of techniques commonly used in the organic chemistry laboratory. Through these experiences we will learn to perform organic chemical reactions as well as some organic laboratory operations, such as use of ground glass chemical apparatus, melting point determination, recrystallization, vacuum filtration, distillation (several types), extraction, drying, evaporation, and gas chromatography.

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

May 20        1.1-7,9-18                     Syllabus and Introduction
                                             Carbon Compounds and Chemical Bonds 
              Homework problems:
              1.5, 1.6, 1.7, 1.19, 1.22, 
              1.24, 1.25, 1.28, 1.31efgh

LAB, May 21   LAB - See lab syllabus

May 22 2.1-12 Representative Carbon Compounds Homework assignment: 1. Take Two assignment 2. Textbook problems: 1.13, 2.10, 2.12, 2.15, 2.19, 2.30, 2.34, 2.54 LECTURE & LAB, May 23 LECTURE - 6:00 - 8:00 PM 2.13-14 Physical Properties and Molecular Structure 3.1-7,12-17 Acids and Bases in Organic Chemistry Homework: 2.25, 2.27, 2.36, 3.9, 3.16, 3.17, 3.29, memorize Ka table

              LAB  - 8:00 - 10:00 PM - See lab syllabus

May 27 No class, Memorial Day

LAB, May 28   LAB - See lab syllabus

LECTURE & LAB, May 29                        

              LECTURE - 6:00 - 8:00 PM

              Take-two assignment due

              4.1-4                          Alkane Nomenclature and Properties
              Homework:                      Take-two assignment due
                 4.2, 4.8, 4.13,
                 4.23 (skip parts l, m & n),
                 4.28, 4.36, 4.39

              LAB  - 8:00 - 10:00 PM - See lab syllabus

LAB, May 30   LAB - See lab syllabus

June 3 4.16 Introduction to chemical synthesis: The synthon approach 4.8-14 Conformational Analysis of Alkanes and Cycloalkanes Homework: a. Read chapter 5 before class on Wednesday b. Homework problems: 4.15, 4.16, 4.41 c. Outline the synthesis of 2,2-dimethyldecane using organic reactants with six carbons or fewer as your starting materials. (click for solution)

LAB, June 4   LAB - See lab syllabus

June 5 5 Stereochemistry LECTURE & LAB, June 6 *** Opportunity #1 *** (covers material in chapters 1 - 4) Note: during normal "lab time" meet in classroom After opportunity: 6.1-12 Ionic Reactions, Introduction to nucleophilic substitution Take home quiz

               BRIEF LAB TIME - See lab syllabus

June 10 Chapter 5 take-home quiz due 6.13-19 Competitive reaction mechanisms: Substitution vs. Elimination Homework: a. Memorize Table 6.7 b. Homework problems: 6.2, 6.3, 6.5, 6.7, 6.9, 6.12, 6.14, 6.20acde, 6.21ad, 6.23, 6.25, 6.29 June 11 7 Alkenes and Alkynes: Nomenclature, Properties & Synthesis Homework: a. Read ahead into chapter 8 b. Homework problems: 7.1abcd, 7.2, 7.4, 7.6, 7.7, 7.14, 7.15, 7.17, 7.19c, 7.20, 7.21, 7.24, 7.28abcd

LAB, June 12   LAB - See lab syllabus

LAB, June 13   LAB - See lab syllabus

June 17 Chapter 8 Alkenes and Alkynes, Addition Reactions Sections: 1-3, 5-10, 12-15, 18 and 19 Homework problems: 8.2, 8.9, 8.11, 8.13, 8.17, 8.26abcfghimn, 8.29 June 18 Chapter 8 Alkenes and Alkynes, Oxidation Reactions Sections: 16, 17, and 20 --- Loose ends and review for Op#2 Homework: Prepare for Opportunity #2

LAB, June 19   LAB - See lab syllabus
               Lab checkout
               Laboratory examination
LAB, June 20 *** Opportunity #2 *** "Office hour time" with pizza from 6-7 pm Opportunity begins at 7 pm