ORGANIC CHEMISTRY I
Chemistry 212-01/L01
Salem State University, Summer 2019


Irvin J. Levy, ilevy@salemstate.edu
Visiting Professor of Chemistry
Katy van Kirk, Assisting
Lecture: M/W, 9:00am-12:30pm
Laboratory: M/W, 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, 12th ed., Graham Solomons & Craig Fryhle. Amazon link
2. The Organic Chem Lab Survival Manual, 10th ed., Zubrick. Amazon link
(Recommended) Solutions Manual to Organic Chemistry, 12th ed., Solomons & Fryhle. Amazon link

ADDITIONAL MATERIALS

1. Bound notebook for laboratory
2. Safety goggles as required by Department
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.

Occasionally, in place of a quiz you may be assigned a take home project that will be collected in a future class and averaged into the quiz score. Usually, you are permitted to work with others on such an assignment provided you follow these rules:

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

1. All students are expected to be familiar with the academic regulations, including those regarding Academic Integrity, for Salem State University as published in the college catalog. In addition, each student is responsible for completing all course requirements and for keeping up with all that goes on in the course (whether or not the student is present).

2. 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.

3. In the event of a university declared critical emergency, Salem State University reserves the right to alter this course plan. Students should refer to salemstate.edu for further information and updates. The course attendance policy stays in effect until there is a university declared critical emergency. In the event of an emergency, please refer to the alternative educational plans for this course located at/in [faculty member determines this]. Students should review the plans and gather all required materials before an emergency is declared.



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 20        Chapter 1                      Syllabus and Introduction
              Skip section 8, 13B            Carbon Compounds and Chemical Bonds 
              Skim section 9
              
              Textbook practice problems:
              1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 
              1.11, 1.12, 1.14, 1.15, 1.28, 
              1.32, 1.35abcdefg, and
              online problems                (solutions for online problems here)




LAB           After lab read: Z1, Z2         Orientation
                                             Lab notebook handout
                                             
                                             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
                                                 
                                             Chemexper web page
May 22 2.1-2.12 Representative Carbon Compounds 1.12-1.14 (review) Homework assignment: 1. COLLECTED! Take Two assignment; Top 100 drugs list 2. Textbook practice problems: 1.22, 2.3, 2.5, 2.9, 2.10, 2.12, 2.15, 2.17, 2.21, 2.22, 2.29, 2.30, 2.34 3. Prepare for Wednesday lab (look up substances & reading procedure and Zubrick)


LAB           Z1, Z2                         Safety discussion, Check-in to lab
                                             1. "Powers of Observation"
              Solomons 2.15-16, Z32          2. 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
                                                

May 27 --- No class, Memorial Day - MAKEUP LECTURE JUNE 1 May 29 READING 2.13-14 Physical Properties and Molecular Structure 3.1-3, Acids and Bases in Organic Chemistry 3.5-7, 3.12, Slides from lecture powerpoint 3.14-15 pKa table - for reference only Take-two assignment collected Homework assignment: 1. Begin to memorize Prof. Levy's Ka table (not the huge one above!) 2. Textbook practice problems: 2.25, 2.27, 2.38 3.1, 3.3, 3.6, 3.7b, 3.9, 3.18, 3.19, 3.20, 3.21, 3.28, 3.38a Optional Sporcle practice quiz: Estimating Ka values


LAB           Z3, Z12                        Melting Point & Its Significance
                                             Continue with chemical calculation sheet
May 31 SPECIAL LECTURE DAY Make up lecture for Memorial Day Holiday 4.8 - 4.13 Conformational Analysis of Alkanes and Cycloalkanes Homework: 1. Textbook practice problems: 4.13, 4.15, 4.16, 4.17, 4.18, 4.43 2. Finish Chemical Calculations handout 3. Be sure Ka table is memorized for quiz next time 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!


             No lab today



June 3 4.1-4, 4.7 Skip 4.4B Alkane Nomenclature, Properties Homework: 0. Advance reading - Chapter 4.8 - 4.14 1. Textbook practice problems: 2.11, 2.13, 2.14, 2.16, 4.2, 4.8, 4.23abcdefghijklo, 4.24abcdf 2. Finish memorizing Prof. Levy's Ka table 3. Prepare for next lab Optional Sporcle practice quiz: Alkane nomenclature


LAB           Z4, Z17, Z18, Z19, Z20, Z32    Purification of volatile liquids
                                             Simple (today!) and Fractional Distillation
                                             
                                             Chemical Calculation sheet is due.
June 5 NMR Spectroscopy; Reading, Study Problems, and Optional Video Links No class meeting today -- at home assignment: 1. Quick overview Reading: 9.1-9.3 2. Number of Sets of Peaks and their Location Reading: 9.4-9.5 Homework: 9.1, 9.3, 9.4, 9.6 (try several) OPTIONAL! Video on sets and area (use only if needed) OPTIONAL! Video on location (use only if needed) 3. Splitting of peaks into sub-peaks Reading: 9.6, SKIP section 9.6C Homework: 9.9, 9.22 OPTIONAL! Video (use only if needed) 4. Carbon-13 NMR Reading: 9.8A and 9.8B 5. Problem solving Homework: 9.35 (try three of these, one from near the beginning, one from the middle, one from the end. If you get all three right, good job. Otherwise, try three more until you either get all of them correct or you run out of examples!) OPTIONAL! Video (use only if needed) HOMEWORK ASSIGNED TODAY: Take home quiz assigned (see email) - Due on June 10 as part of Opportunity #1 LAB No lab today
June 10 8:30-9:30 AM Zoom meeting Q&A for the opportunity


Lab            In the lab space 
               Opportunity #1 - chapter 1-4, no synthesis
               with Katy van Kirk 
               NMR Take Home Due
                                         
                                             
June 12 Worksheet assignments from home or together 4.15, 4.16, 7.18 Synthesis of Alkanes worksheet Chapter 5 Stereochemistry worksheet Homework: 1. Textbook practice problems: 4.19, 7.25, 7.26 2. Outline the synthesis of 2,2-dimethyldecane using organic reactants with six carbons or fewer as your starting materials. (click for solution) Homework: Complete worksheets TBA


              Assisted by Katy van Kirk
              
LAB           Z4, Z17, Z18, Z19, Z20, Z32    Purification of volatile liquids
                                             Simple and Fractional Distillation (today!)


June 17 Chapter 6 Reaction types Ionic Mechanisms Competitive reaction mechanisms: Acid/Base Nucleophilic Substitution Elimination Worksheets on Synthesis and Stereochemistry are due. Read chapter 6 Homework: Textbook practice problems: 6.2, 6.3, 6.7, 6.8, 6.10, 6.14, 6.15, 6.16, 6.20acde, 6.21ad, 6.23, 6.25, 6.29, 6.35 Optional Sporcle practice quiz:
Predicting reaction type


Lab             ---                          Select the greener way to prepare an alkene:

                                             Dehydration of an alcohol: Preparation of methylcyclohexenes
                                             
                                             -or-  
                                             
                                             Montmorillonite-clay catalyzed dehydration
                                             
June 19 7.1-17 Alkenes and Alkynes: Nomenclature, Properties & Synthesis 7.1abcd, 7.2, 7.4, 7.6, 7.7, 7.11, 7.12, 7.13, 7.15, 7.21, 7.22, 7.37abceghi Begin Chapter 8 Alkenes and Alkynes, Addition Reactions TBA


LAB            Z6, Z9, Z11, Z13              Preparation and purification of dibenzalacetone
                                                                                         

June 24 Finish Chapter 8 Alkenes and Alkynes, Oxidation Reactions TBA


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

                                             Lab checkout
June 26 9:00-10:00 AM Office hours (in lab) 10:00-12:30 AM *** Opportunity #2 *** Cumulative rections, reagents, mechanisms, NMR 1:00-2:00 PM Laboratory examination (open lab notebook)