ORGANIC CHEMISTRY I
Chemistry 212-01
Salem State University, Summer 2014


Irvin J. Levy, ilevy@salemstate.edu
Visiting Professor of Chemistry
Lecture: M/W, 9:00am-12:30pm
Laboratory: M/Th, 1:00pm-4:30pm
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. We will seek to do this in ways that are consisent with the principles of green chemistry.

Catalog description:

Introduction to chemistry of carbon compounds. Survey of the principal classes of aliphatic and aromatic compounds and their reactions. The application of the techniques of synthetic organic chemistry to the preparation and purification of simple organic compounds is taken up in the laboratory. Required of Chemistry and Biology Majors. Three lecture hours, and one three-hour laboratory per week. This course, with CHE130 satisfies the full year sequence in a laboratory science.
Prerequisite: CHE130.

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.

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 not possible 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 day. This will result in two reductions to the lab grade (chemical hygiene violation, nonexcused absence).

To assure that students come to lab prepared for the day's activities, a brief open-notebook quiz will often be administered at the beginning of the lab session.

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. 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

Salem State University is committed to providing equal access to the educational experience for all students in compliance with Section 504 of The Rehabilitation Act and The Americans with Disabilities Act and to providing all reasonable academic accommodations, aids and adjustments. Any student who has a documented disability requiring an accommodation, aid or adjustment should speak with the instructor immediately. Students with Disabilities who have not previously done so should provide documentation to and schedule an appointment with the Office for Students with Disabilities and obtain appropriate services.



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.

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.

Note: Laboratory is preceeded by a mandatory pre-lab lecture and quiz. Handouts will be provided online (links below) or in hard copy. Reading in the Organic Chem Lab Survival Manual is indicated by chapters beginning with the letter Z.


Date          Reading assignment             Topic

May 19        1.1-7,9-17                     Syllabus and Introduction
                                             Carbon Compounds and Chemical Bonds 
              Homework 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  After lab read: Z1, Z2          Orientation
                                             Lab notebook handout

                                             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
                                                 
                                             Chemexper web page
May 21 2.1-2.12 Representative Carbon Compounds 1.12B-1.14 (review) Homework assignment: 1. COLLECTED! Take Two assignment; Top 100 drugs list 2. Textbook problems: 1.22, 2.10, 2.12, 2.15, 2.17, 2.21, 2.22, 2.29, 2.30, 2.34


LAB, May 22   Z1, Z2                         Safety discussion, Check-in to lab
                                             1. "Powers of Observation"
              Solomons 2.15-16, Z32          2. Infrared Spectroscopy: Functional group analysis

                                                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
                                                

May 26 No class, Memorial Day - MAKEUP LECTURE MAY 30 May 28 3.1-7,3.12-16 Acids and Bases in Organic Chemistry pKa table - for reference only Slides from lecture powerpoint Take-two assignment due Class ends early today Homework assignment: 1. Memorize Prof. Levy's Ka table (not the huge one above!) 2. Textbook problems: 3.1, 3.2, 3.4, 3.6, 3.9, 3.16, 3.18, 3.19, 3.32 After tomorrow's brief lecture: 2.25, 2.27, 2.38, 2.41 Optional Sporcle practice quiz: Estimating Ka values


LAB, May 29   2.13-14                        Physical Properties and Molecular Structure

              Z3, Z12                         Melting Point & Its Significance
                                             Continue with chemical calculation sheet
May 30 4.1-4, 4.8-14 SPECIAL LECTURE DAY, 9:00 - noon (DGCE Makeup Day for Memorial Day Holiday) Alkane Nomenclature, Properties Conformational Analysis of Alkanes and Cycloalkanes Homework: 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
June 2 4.16 Synthesis of Alkanes Conformational Analysis of Alkanes and Cycloalkanes Homework: 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 reactants with six carbons or fewer as your starting materials. (click for solution) 3. Prepare for Opportunity #1 - summarize chapters


LAB, June 2   Z4, Z17, Z18, Z19, Z20, Z32    Purification of volatile liquids
                                             Simple and Fractional Distillation
                                             Chemical Calculations sheet due

June 4 5 Stereochemistry Homework: 1. PREPARE FOR OP#1! The following homework is not part of Op#1 - wait until after class tomorrow 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 5                                *** Opportunity #1 ***
                                             (covers material in chapters 1 - 4)
                                             Note: 1:00 pm during normal "lab time"
                                                   meet in laboratory space
                                             

June 9 6 Ionic Mechanisms 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 9    Z6, Z9, Z11, Z13              Preparation and purification of dibenzalacetone
                                             

June 11 7.1-16 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 12        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 16 Chapter 8 Alkenes and Alkynes, Oxidation Reactions Sections: 16, 17, and 20 Textbook practice problems: 8.15, 8.17, 8.20, 8.21, 8.27ghjkl, 8.29, 8.53


LAB, June 16                                 Multi-tasking Instrumental Day!
               Z32                               1. Gas Chromatography of distillate 
               Solomons 2.16, Z34                2. IR of previous products
                                                 3. Melting point of previous product 
                                                 

June 18 Solomons 9.1-9,10 Identification of molecules by NMR spectroscopy Z35 Homework: 0. Prepare for chapter 8 quiz on Monday 1. Textbook practice problems for chapter 9: 9.2, 9.3, 9.4abc, 9.38 (try a few at random) 2. Take home quiz on NMR (also due Monday) - sent via email


LAB, June 19   ---                           Select the greener way to prepare an alkene:

                                             Dehydration of an alcohol: Preparation of methylcyclohexenes
                                             -or-  Montmorillonite-clay catalyzed dehydration: Greener options


June 23 10, selected sections Radical reactions: An overview


LAB, June 23   handout                       Bromination of an alkene: Dibromostilbene
                                               
                                             NMR Take Home Due
                                             Lab checkout
                                             Laboratory examination            
June 25 No meeting today STUDY DAY - Prepare for final exam June 26 *** Opportunity #2 *** Meet in lab classroom, MH544