CHEM 2319-2 Spring 2008
Organic Chemistry

MWF 9:30 - 10:20 SLH

Instructor: Dr. Steven Bachrach

Office: 215D MEB

email: sbachrach@trinity.edu

phone: 999-7379

Office Hours: MWF 1:00-2:00pm or by appointment

HHMI Peer tutor: Clint Fuller

6:00pm - 7:15pm MTh (106 MEB)

Study Sessions: Tuesday 5-6 MEB 105
                Dr. Mills help session: Tuesdays 4-5 in MEB 103

Text:
                John McMurry, Organic Chemistry, Seventh Edition (required)
                David R. Klein, Organic Chemistry as a Second Language (required)
                Susan McMurry, Study Guide and Solution Manual (recommended)

Description:

This is the first semester of a two-semester sequence of organic chemistry. We will roughly follow the order of topics covered in the text as we discuss material from chapters 1 through 16 (don't panic, some of these chapters are short). Familiarity with concepts learned in introductory chemistry course such as electronegativity, Lewis structures, resonance, acid/base chemistry will be beneficial. The course will emphasize functional groups, structure, nomenclature, physical properties, reaction and reaction mechanisms. The corresponding lab course, Chem 2119, is a corequisite and all students must remain enrolled in both courses. Any student who fails to meet this corequisite will be dropped from 2319.

Grading:

Your grade for the course will be based on your highest three exam scores (out of four), your six highest quiz scores (there will be at least 7 quizzes) and the final exam. Each exam is worth 100 points for a total of 300 points possible, each quiz is worth 10 points for 60 possible points and the final exam is worth 140 points. The grade scale for will be discussed in class after each exam; the scale will be no more severe than >90% A, >80% B, >70% C, >60% D, <60% F. Exam dates are listed in the tentative course outline; quiz dates will be announced in class.

Quiz Scores:60 points
Top 3 Exams:300 points
Final Exam:140 points
Total:500 points

Make-ups:

No late or make-up exams will be given. If you miss an exam it will automatically become the exam you drop. Note that any subsequent missed exam will receive a score of zero. If you know in advance that you will be absent for one of the exam dates you must inform me at least one week in advance and we may arrange for an alternate time for your exam.

Web Site: www.trinity.edu/sbachrac/chem2319

Online Molecular Structures: hackberry.chem.trinity.edu/SMB/chem2319/structuresJ1.html

Homework:

Relevant homework problems from the textbook will be announced periodically throughout the class. No homework will be collected or graded, however, I am happy to check/discuss your answers in office hours and study sessions. The homework problems listed below are representative of the kinds of questions I will ask on the tests and quizzes. These are the minimum number of homework problems I would expect every student to work out. If you are having difficulties, l you should try additional problems in the textbook, or find any other textbook (or the Internet) for additional problems.

Chapter 1

25, 26, 30, 31, 33, 38, 49, 52

Chapter 2

27, 32, 34, 35, 37, 40, 43, 53, 56

Chapter 3

30, 38, 42, 48

Chapter 4

25, 31, 34, 40, 48, 52, 54

Chapter 5

21, 22, 23, 30, 38

Chapter 6

23, 26, 28, 30, 31, 36, 39, 42, 44, 47, 48, 53, 58

Chapter 7

25, 26cd, 28, 38, 42, 43(not c), 46, 55, 56

Chapter 8

18, 19, 22, 23, 24, 28, 31, 35, 35, 41, 45

Chapter 9

31, 33, 37, 39, 44, 45, 50, 52, 61, 63, 64, 72, 77, 81, 82

Chapter 10

17, 18, 21, 23cefg, 25, 27, 30, 32, 36, 37

Chapter 11

25, 28, 30, 34, 36, 38, 41, 45, 47, 52, 56, 58, 64

Chapter 12

14, 21, 32, 34, 44

Chapter 13

32, 36, 38, 42, 44, 46, 49, 50, 52, 53, 57, 66, 67

Chapter 14

20, 24, 27, 32, 36, 40, 43, 50, 55

Chapter 15

18, 20, 25, 32, 33, 36, 45, 46

Chapter 16

30, 32, 35, 36, 38, 43, 46, 48, 52, 60, 64, 70, 73

Honor Code Policy:

All students are covered by a policy that prohibits dishonesty in academic work. The Academic Honor Code covers all those who entered the fall of 2004 or later. Under the Code, a faculty member will (or a student may) report an alleged violation to the Academic Honor Council. It is the task of the Council to investigate, adjudicate, and assign a punishment within certain guidelines if a violation has been verified.

Students who are under the Honor Code are required to pledge all written work that is submitted for a grade:  "On my honor, I have neither given nor received any unauthorized assistance on this work" and their signature.  The pledge may be abbreviated "pledged" with a signature.

All exams and quizzes will be subject to the honor code, and each must be done individually. If we have some group assignments, I will inform you of how this will be handled under the Honor Code at that time.

Tentative Course Outline

   :    :    :

Section 1. Chapters 1-4,6

Atomic structure, bonding, hybridization, Lewis structures, resonance, acids and bases, drawing molecules, nomenclature, Conformations of alkanes, Conformations of cycloalkanes
Alkenes: nomenclature and stability

Exam 1: Monday February 11, 2008

Section 2. Chapters 5-8

Polar and radical reactions, Describing organic reactions
Alkenes: electrophilic addition, electrophilic addition, carbocations, carbocation rearrangements, Hammond postulate, preparations and reactions, polymers
Alkynes: preparation and reactions, acetylide anions, organic synthesis, problem solving

Exam 2: Wednesday March 5, 2008

Section 3. Chapters 9-11

Stereochemistry: nomenclature, drawing, chirality, R and S, enantiomers and diastereomers, stereochemistry of reactions, chirality in nature, Alkyl halides: preparations and reactions, radicals, Nucleophilic Substitution, Sn1 and Sn2, Elimination, E1 and E2, Substitution vs Elimination, Problem Solving

Exam 3: Wednesday April 2, 2008

Section 4. Chapters 12-16

IR and Mass spectroscopy, NMR spectroscopy, Problem Solving, Conjugated dienes
Aromaticity: naming, rules, ions, heterocycles, polycycles, spectroscopy, electrophilic substitution reactions

Exam 4: Wednesday April 23, 2008

Section 5. Chapter 16

substituent effects, Nucleophilic Aromatic Substitution, Organic Synthesis, Course Review

Comprehensive Final Exam: Monday May 12, 2:00pm

Please note that I will try very hard to follow this schedule. However, the only rigorously maintained items on the schedule are the dates of the exams.

Tips for Success in Organic Chemistry

First, you must dispel any rumors regarding how difficult this course is. As you will find, organic chemistry is a very logical subject. Once you understand its principles and trends, the material will make sense and become predictable. Second, do not get behind.We will work at a fairly rapid pace where new material builds on principles learned in earlier chapters. If you do not understand these early chapters, subsequent topics will be much more difficult. If you encounter trouble, get help early! I highly recommend reading ahead of lecture so our class discussion can answer any questions you may have from the text. Third, work as many homework problems as you possibly can. When doing homework, do not rely too heavily on the solutions manual to obtain the answer. You will learn much more if you struggle through a problem yourself or if you ask for help. Once you understand the solutions you should re-attempt to solve the problem on your own the next day. The small paperback by Klein, Organic Chemistry as a Second Language, is a wonderful book. It takes the material from your text and summarizes it in a very readable fashion. It captures the hardest concepts to master and discusses them in a very accessible way. Don't forget to read it! Lastly, when doing these homework questions and studying for the exams, try to avoid simply memorizing the material. While some material you will simply need to remember, the majority of organic chemistry is best learned by recognizing the underlying principles and patterns.

I want to re-emphasize that if you are having difficulties with the homework problems, please seek help early on. Waiting until after the test to find out how to work certain problems will do nothing to improve that score. Our peer tutor, Clint Fuller will be available at scheduled office hours. I am available at office hours and by appointment and at help sessions. There is no reason not to take advantage of these resources being made available to you - and I am that principle resource! I monitor my email pretty regularly and am happy to answer your questions using email. Keep in mind however that organic chemistry is very much a visual science - we will be constantly writing out structures, mechanisms and reactions - something that is difficult to do via email. So, don't count on email as a primary means for getting your questions answered.

Test Answers

Quiz Answers