Organic Chemistry

Chemistry 2311

Fall 1996

Dr. James E. Hanson Lecture: MWF 11:00-11:50 Science Amph.
422 McNulty M 4:30-5:20 Corrigan 64
761-9416Laboratory: Tuesday or Thursday, AM or PM
email: hansonja@lanmail.shu.edu McNulty 221 or 223
homepage: http://www.shu.edu/~hansonja/ Office Hours: M 3:00 - 4:00 PM
T/R 3:00 - 5:00

Textbooks

Organic Chemistry, 6th edition, T.W.G.Solomons

Organic Chemistry Study Guide 6th edition, Solomons & Fernandez

Organic Nomenclature: A Programmed Introduction, J.G.Traynham

Organic Experiments, 7th edition, Fieser & Williamson

Supplemental Materials

molecular model kits (recommended, not required)

Objectives

The students who successfully complete this course will master a body of knowledge concerning several classes of organic compounds: the alkanes, alkenes, alkynes, haloalkanes, alcohols, and ethers. This body of knowledge includes structure, nomenclature, chemical properties, physical properties, and spectroscopy. Successful students will learn the reactivities of these compounds, being able to predict products given starting materials and to suggest appropriate routes of synthesis. They will understand reactivities using reaction mechanisms and simple theories of resonance and electrostatic stabilization. They will understand the stereochemistry of organic compounds and the relationship of the various reactions to the stereochemistry of reactants and products. They will apply this knowledge in the laboratory, where they will learn the roles of both synthesis and analysis in organic chemistry. Above all, the successful student will have learned to think analytically about problems in organic chemistry, and will not rely solely on rote memorization.

Grading
Examinations 4 x 100 = 400 points
Final Examination 150 points
Literature Project 100 points
Laboratory200 points
TOTAL850 points
Assignments/Quizzes pass/fail

Policies

Learning organic chemistry requires consistent effort. To encourage and promote this effort, an assignment or quiz will be given each week. These assignments or quizzes will generally be administered on Fridays and/or Mondays. Four one hour exams will be given during the semester. Each will emphasize the most recent material, but as knowledge gained earlier in the course (and in prior prerequisite courses) may be necessary for understanding the problems, all exams can be considered essentially comprehensive. Exams will be short answer questions and problems, there will be no multiple choice. Exams will be scored and returned within one week. Upon return, the exam scores will be open for discussion for one week. Except for arithmetic mistakes, exams will only be re-scored in their entirety by the instructor: individual problems will not be re-scored. The final exam will be comprehensive. No make up tests will be given. In the event that an exam must be missed due to a documented medical or other legitimate emergency, the 100 point value of that exam will be added to the final exam. Sets of suggested problems from each chapter will be provided by the instructor. These problems should be worked, but will not be collected. Answers to these problems can be found in the study guide.

ACADEMIC DISHONESTY WILL NOT BE TOLERATED. ANY STUDENT FOUND CHEATING ON AN EXAM OR QUIZ OR PLAGIARIZING OR FALSIFYING A LABORATORY NOTEBOOK WILL BE GIVEN A ZERO FOR THAT EXAM, QUIZ, OR LAB. A LETTER DESCRIBING THE OFFENSE WILL THEN BE PLACED IN THAT STUDENTÍS PERMANENT RECORD. A SECOND INFRACTION WILL RESULT IN DISMISSAL FROM THE COURSE AND A FAILING GRADE.

Laboratory

Safety: The laboratory contains many potential hazards and safety must be taken extremely seriously. Failure to observe safe operating procedures will result in expulsion from the laboratory for the day. A second safety violation will result in permanent expulsion and a zero for the laboratory portion of the grade. Appropriate attire is required at all times in the laboratory as part of safe laboratory practices. This begins with safety glasses and includes long pants or skirts. Shorts, bare feet, and open-toed sandals are NOT permitted. Lab coats and gloves are recommended.

Preparation and Notebook Keeping: Preparation is essential for safety and efficiency in the laboratory. No one will be permitted to work in the lab who has not documented their preparation in the laboratory notebook. This pre-lab preparation will be checked at the beginning of each lab period. As is the practice in all industrial and research laboratories, the notebook will be the primary document for the laboratory. (Most students will have learned how to maintain a laboratory notebook in General Chemistry. Those who have not should purchase Writing the Laboratory Notebook by H.M.Kanare, available in the bookstore.) To have your laboratory grade applied toward the total grade, a complete and satisfactory laboratory notebook is required. Notebooks will be collected and examined every third or fourth week, and any unsatisfactory experimental write-ups will be noted and will require correction.

Grading: The grade for the laboratory will be based on performance in laboratory examinations or practicals. There will be three of these practicals during the semester, and they should be prepared for as thoroughly as any written lecture exam. Each practical will be worth 60 points A written laboratory safety quiz will make up the final 20 points of the lab grade.

Evaluation

All students who complete all of the quizzes and assignments without errors and who attend and complete all laboratory experiments and submit a complete and satisfactory laboratory notebook, while scoring at least a 50% (after renormalization - see below) of the high grade will be assured a minimum grade of D+. These students may earn a higher grade based on their performance on the lecture exams, final, literature project, and lab practicals. All grades will be assigned based on a renormalization protocol. The high grade in the class will be assigned a value of 100% and all other percentages will be calculated from this norm. The scale will be:
A> 90%
B+87.5 - 89.9%
B80.0 - 87.4%
C+77.5 - 79.9%
C70.0 - 77.4%
D+67.5 - 69.9%
D60.0 - 67.4%
F< 60%

Note that since the normalization value (the high score) will not be known until grades for all components of the course are complete, it is difficult to define a grade with any accuracy until the end of the course.

Examinations
Approximate Date Tentative Topics
September 23 Chapters 1 - 4
October 21Chapters 4 -8
November 19Chapters 7,8,10,11
December 13Chapters 10, 11, 9, 13
FINAL: December 20, 10:45 AM CUMULATIVE

Last day for withdrawal: October 18

Schedule of Lecture Topics

Introduction and Review (Chapters 1 & 3)

Nomenclature and Functional Groups (Chapter 2)

Alkanes (Chapter 4)

Stereochemistry (Chapter 5)

Heterolytic Reactions (Chapters 6)

Alkenes and Alkynes (Chapters 7 & 8)

Alcohols and Ethers (Chapters 10 & 11)

Homolytic Reactions (Chapter 9)

Spectroscopy (Chapter 13)

Schedule of Laboratory Experiments

(Schedule subject to adjustment with at least one week's notice.)

Laboratory meets in 221 and 223 McNulty
8/27 & 8/29 Check In
9/3 & 9/5 Recrystallization and Melting Points (Exp. 3 & 4)
9/10 & 9/12 Distillation (Exp. 5)
9/17 & 9/19 Extraction (Exp. 8)
9/24 & 9/26 Thin Layer Chromatography (Exp. 9)
10/1 & 10/3 Practical #1: Separation and Purification
10/8 & 10/10 1-Bromobutane
10/15 & 10/17 Fall Break: No Labs
10/22 & 10/24 Benzoic Acid (Exp. 31 with handouts)
10/29 & 10/31 Cyclohexene (Exp. 11)
11/12 & 11/7 Practical #2: Synthesis
11/19 & 11/14 Nucleophilic Substitution (Exp. 14)
11/26 & 11/21 Biosynthesis of Ethanol (Exp. 18)
12/3 & 12/5 Practical #3: Synthesis and Purification
12/10 & 12/12 Check Out