ORGANIC CHEMISTRY II
Chemistry 212
Gordon College, Summer 2016


Irvin J. Levy, irv.levy@gordon.edu
Professor of Chemistry
T/Th, 2:00pm-10:00pm
Dinner break will be scheduled daily
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.

This second semester course assumes a working knowledge of the material from the first semester of the course. For reference, the syllabus from the first course is available online.

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. Opportunity #2 is the American Chemical Society's examination for Organic Chemistry. Students who perform at the 90th percentile or higher on this exam will receive an automatic grade of A for the course, provided all laboratory work is completed. A 164-page study guide for this exam is available for purchase online.

Two low quiz scores will be dropped when computing the final quiz grade. Make-up quizzes are not available.

Laboratories during the second semester build from the techniques practiced during the first semester. Specifically, students should be familiar with the use of ground glass chemical apparatus, infrared spectroscopy, melting point determination, recrystallization, vacuum filtration, distillation (several types), extraction, drying, and evaporation.

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)
          20% - Laboratory
           5% - Lecture Engagement

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.

Date          Reading assignment            Topic

June 28       Special Start Time - 5:00 PM

              chap. 11 skip sections:       Alcohols and Ethers
              11.11CDE, 11.16
               
              Homework: 
              1. Quickstart review of reactions
              2. Textbook practice problems:
                  11.2, 11.3, 11.5, 11.6, 11.9,
                  11.12, 11.16, 11.18, 11.26ade,
                  11.33, 11.34 (skip GHI), 11.37 
              3. READ AHEAD (important!) - Chapter 12.1-12.8          



LAB           No lab tonight
    
June 30 Special Start Time - 5:00 PM Work on draft of chapter 1-11 reaction database 12.1-8 Oxidation & Reduction of Carbonyl Compounds The Grignard Reaction Textbook practice problems: 12.3, 12.5abc, 12.7, 12.8, 12.9abcd, 12.10, 12.12, 12.28 (good review!), 12.32abc


LAB           Lab - NMR Demonstration



July 5 13.1-8,10,11 Resonance - Conjugation - Delocalization - Stability Diene reactions: o conjugate addtion o the Diels-Alder reaction Textbook practice problems: 13.2, 13.3, 13.4, 13.6, 13.25, 13.31 Diels-Alder questions: 13.14, 13.15, 13.16, 13.43abcde


LAB           Z9, Z10, Z24                  Sodium borohydride reduction of a ketone:
                                            Preparation of meso-hydrobenzoin
                                            
              ---                           Preparation of Benzaldeyhde by Greener Oxidation:           
                                                Part A. Preparation of octamolybdate catalyst
                                            
July 7 14 Aromaticity 15.1-2 Introduction to the reactions of aromatic molecules Homework: 0. Try some practice problems with this online quiz 1. Textbook practice problems: 14.1acd, 14.16abcdefghknmpqr, 14.18, 14.21 2. Work on take-home quiz (see email)


LAB           ---                           Preparation of Benzaldeyhde by Greener Oxidation:           
                                                Part B. Preparation of benzaldehyde





              -- SPECIAL SCHEDULE THIS WEEK -- 

July 14 15.3-16 Reactions of aromatic molecules, continued Textbook practice problems: 15.4, 15.7, 15.8, 15.11, 15.16, 15.31, 15.32abcdehim, 15.36a


LAB           Z4, Z13, Z22, Z23             Electrophilic aromatic substitution:
                                                Preparation of iodovanillin (paper handout)  


July 15 16.1-16.8,16.10-16.14 Aldehydes and Ketones Special Topic G.2 Nomenclature, Synthesis (found between pgs Reactions: Nucleophilic addition 978 and 979 in text) Ammonia addition compounds Wittig reactions and Greener Alternatives Link to Nobel Prize site: Grubbs lecture Metathesis animation Metathesis dancers Textbook practice problems: 16.1a, 16.2, 16.3a, 16.4abcde, 16.6, 16.9, 16.12, 16.13, 16.17abcde, and Practice problem G.9 in the Special Topic Section


LAB           ---                           A. Heterocyclic amines via imine formation: Synthesis of a quinoxaline                                                                                  
                                            B. Microwave-assisted synthesis of benzil from benzoin (handout)
                                            




              -- SPECIAL SCHEDULE THIS WEEK -- 

July 20 *** Opportunity #1 *** Chaps. 11 - 15 (2:00-4:00 PM) Dinner break - 4:00-5:00 PM 5:00 PM 17 Carboxylic acids and their derivatives

LAB           ---                           CLASS ASSISTED DEMONSTRATIONS - 

                                            Esterification: Preparation of fragrant esters (handout)
                                            Saponification: Preparation of soap (handout)

July 21 18.1-3,5-8,10 Enolate Chemistry - Part I (skip 18.3D) Tautomerization Haloform reaction Active methylene syntheses w/ acetoacetic ester & malonic ester 19.1,2,4-7 Enolate Chemistry - Part II Claisen condensation Aldol reactions Claisen-Schmidt reaction Demo: Preparation of dibenzalacetone 20.1-7,12 Amines 21 Phenols; Nucleophilic Aromatic Substitution

No lab tonight


July 26 Q&A, Study session for Final Exam


LAB           Finish all prior lab work; Lab exam

July 27 Optional: Study session July 28 Office hours 2:00 - 5:00 PM *** Opportunity #2 *** 5:00 - 7:00 PM July 29 Sit back and relax. You made it!