ORGANIC CHEMISTRY I
Chemistry 211
Gordon College, Summer 2015

Irvin J. Levy, irv.levy@gordon.edu
Professor of Chemistry
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.

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

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 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.

USEFUL WEB RESOURCES


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 18        1.1-7,9-18                     Syllabus and Introduction
                                             Carbon Compounds and Chemical Bonds 

              Textbook practice problems:
              
              1.2, 1.3, 1.5, 1.6, 1.7, 
              1.11, 1.14, 1.15, 1.28, 
              1.32, 1.35abcdefg, and
              online problems                (solutions for online problems here)




LAB, May 19   LAB - See lab syllabus


                     
                                            
May 20         2.1-12                        Representative Carbon Compounds
               1.12B-1.14 (review)

               Homework problems:

               1. COLLECTED! Take Two assignment; Top 100 drugs list               
               2. Textbook practice problems:
                  1.22, 2.10, 2.12, 2.15, 2.17,
                  2.21, 2.22, 2.29, 2.30, 2.34
                  
LECTURE & LAB, May 21  

              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  
              
                                             Slides from lecture powerpoint 
              Homework assignment:           
            
              1. Memorize Prof. Levy's Ka table (not the huge one above!)
              2. Textbook practice problems:
                 2.25, 2.27, 2.38, 2.41,
                 3.1, 3.2, 3.4, 3.6, 3.9, 3.16, 
                 3.18, 3.19, 3.32
                 



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


                     




May 25                                      No class, Memorial Day


May 26        Take-two assignment due

              4.1-4                          Alkane Nomenclature and Properties
              (skip 4.3F, 4.4B)
              
              Textbook practice problems:    
              2.11, 2.13, 2.14, 2.16,
              4.1, 4.2, 4.6, 4.8abcd,
              4.23abcdefo, 4.24abc                           
                                  
 
May 27        4.16                           Introduction to chemical synthesis: The synthon approach
              4.8-14                         Conformational Analysis of Alkanes and Cycloalkanes                     
              



LAB, May 28   LAB - See lab syllabus
              

 
                                            



June 1        5                              Stereochemistry




LAB, June 2   LAB - See lab syllabus


                     

June 3                                       *** Opportunity #1 ***
                                             (covers material in chapters 1 - 4)
                                             
                                             After opportunity:
               6.1-12                            Ionic Reactions, Introduction to nucleophilic substitution
               


               
LAB, June 4   LAB - See lab syllabus


                     




June 8                                       Chapter 5 take-home quiz due

               6.13-19                       Competitive reaction mechanisms: Substitution vs. Elimination
                  




LAB, June 9   LAB - See lab syllabus


                     
  
June 10        7                             Alkenes and Alkynes: 
                                             Nomenclature, Properties & Synthesis
  



LAB, June 11   LAB - See lab syllabus
                                             

                     

   

                                          
            
June 15        Chapter 8                     Alkenes and Alkynes, Addition Reactions

June 16        Chapter 8                     Alkenes and Alkynes, Oxidation Reactions
               Chapter 10                    Brief Survey of Radical Reactions
               



LAB, June 17   LAB - See lab syllabus
  
               Lab checkout
               Laboratory examination
               

                     

LAB, June 18   *** Opportunity #2 ***