ORGANIC CHEMISTRY I
Chemistry 211
Gordon College, Summer 2016


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 23        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 24   1, Z2                          Orientation
                                             Lab notebook handout
                                             Safety Discussion
                                             
                                             Green Chemistry Metrics
                                             Organic Chemistry Calculations
                                             Formula weight calculator
          
                                             Lab prep always includes, for every substance that we use:

                                                 Name
                                                 Structural drawing
                                                 Molecular weight
                                                 GHS Signal Word
                                                 Hazard pictograms
                                                 Hazard statements
                                                 If solid, melting point
                                                 If liquid, density & boiling point
                                                 
                                             ACTIVITY: "Powers of Observation"    
May 25 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 May 26 LECTURE 2.13-14 Physical Properties and Molecular Structure 3.1-7,12-17 Acids and Bases in Organic Chemistry pKa table - for reference only 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 Optional Sporcle practice quiz: Estimating Ka values
May 30 No class, Memorial Day May 31 LECTURE TODAY 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 Optional Sporcle practice quiz: Alkane nomenclature


LAB, June 1   LAB TODAY
 
              Solomons 2.15-16, Z32  Infrared Spectroscopy: Functional group analysis
                                             Spectral Database for Organic Compounds

                                                Possible substances:
                                                
                                                Alcohols           Ketones            Carboxylic acids
                                                ----------------   ----------------   ----------------
                                                methanol           acetone            acetic acid
                                                ethanol            butanone           propanoic acid
                                                1-propanol         2-pentanone        butyric acid
                                                2-propanol         3-pentanone        2-methylbutyric acid
              
June 2 LECTURE TODAY 4.16 Introduction to chemical synthesis: The synthon approach 4.8-14 Conformational Analysis of Alkanes and Cycloalkanes Homework assignment: 1. Textbook practice problems: 4.19, 4.33, 4.36, 4.38, 4.39, 4.41 2. Outline the synthesis of 2,2-dimethyldecane using organic molecules with six carbons or fewer as your starting materials. (click for solution) 3. Prepare for Opportunity #1 - summarize chapters Optional: molinspiration structure generator To use molinspiration, draw structure and then click Galaxy 3D Generator button WARNING! This software is in development; I have discovered errors. You might, too!
June 6 5 Stereochemistry Homework: 1. PREPARE FOR OP#1! The following homework is not part of Op#1 - wait until after the opportunity to do this study. 2. Textbook practice problems: 5.1, 5.4, 5.5, 5.6, 5.10, 5.11, 5.12, 5.13, 5.15, 5.19, 5.20, 5.22, 5.38, 5.40abcdefgmnop, and 5.52 (best problem ever!) 3. Optional Sporcle practice quiz: Comparing 3-D structures


LAB, June 7   Z3, Z12                        Melting Point & Its Significance
                                             Continue with chemical calculation sheet

June 8 *** Opportunity #1 *** (covers material in chapters 1 - 4) After opportunity: 6.1-12 Ionic Reactions, Introduction to nucleophilic substitution

               
LAB, June 9   Z4, Z17, Z18, Z19, Z20, Z32    Purification of volatile liquids
                                             Simple Distillation & Fractional Distillation
                                             Chemical Calculations sheet due


June 13 Chapter 5 take-home quiz due 6.13-19 Competitive reaction mechanisms: Substitution vs. Elimination Homework: 0. Correct errors in Op#1 for your own review 1. Memorize Table 6.6 2. Textbook practice problems: 6.2, 6.3, 6.7, 6.8, 6.9, 6.10, 6.14, 6.15, 6.20acde, 6.21ad, 6.23, 6.25, 6.27, 6.29, 6.46 Optional Sporcle practice quiz: Predicting reaction type


LAB, June 14   Z6, Z9, Z11, Z13              Preparation and purification of dibenzalacetone
               
                                             GC analysis of purified liquids from fractional distillation
                                             IR analysis of purified liquids
                                            
                                             Chemical Calculations sheet due

June 15 7 Alkenes and Alkynes: Nomenclature, Properties & Synthesis Textbook practice problems: 7.1abcd, 7.2, 7.4, 7.6, 7.7, 7.11, 7.12, 7.13, 7.15, 7.21, 7.21, 7.22, 7.32agh, 7.34c, 7.41


June 16        9.1-9.4, 9.6-9.9C, 9.9E       NMR Spectroscopy

               Textbook practice problems:
               9.1, 9,2, 9.4, 9.6, 9.9, 9.10, 
               9.25, 9.38 (great practice!)
                                             

June 20 Chapter 8 Alkenes and Alkynes, Addition Reactions Sections: 1-3, 5-10, 12-15, (Hydrohalogenation, Hydration) 18 and 19 Textbook practice problems: 8.1, 8.2, 8.3, 8.6, 8.8, 8.9, 8.11, 8.13, 8.26abfimn, 8.27abfimn June 21 Chapter 8 Alkenes and Alkynes, Oxidation Reactions Sections: 16, 17, and 20 Chapter 10 Brief Survey of Radical Reactions Textbook practice problems: 8.15, 8.17, 8.20, 8.21, 8.27ghjkl, 8.29, 8.53 Chapter 10 problems ...


LAB, June 22   Lab checkout
               Laboratory examination
               
LAB, June 23 *** Opportunity #2 ***