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CHEMISTRY
2319-2 Organic Chemistry I
Spring 2011
MWF 9:30 – 10:20 Chapman 126 (auditorium)
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: Michael Cammarata, office hours: SMT 8-10pm, MEB 106
Study Sessions: Monday 5-6pm
Dr. Mills help sessions: Tuesdays 4-5pm
Textbook:
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 15 (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 are essential. The course will emphasize functional groups,
structure, nomenclature, physical properties, reactions 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 CHEM 2319.
Web Site: http://www.trinity.edu/sbachrac/chem2319
Online Molecular Structures: http://comporgchem.com/chem2319/structures1.html
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. Dr. Mills and I will each write and grade our own exams. Nonetheless,
attending her help sessions might provide an approach that you may find
helpful.
| Quiz Scores: | 60 points |
| Top 3 Exams: | 300 points |
| Final Exam: | 140 points |
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| Total: | 500 points |
Make-ups
No
late or make-up exams will be given. If
you miss an exam for an excused reason it will automatically become the exam
you drop. (What constitutes and excused exam is at the sole discretion of Dr.
Bachrach; examples include illness, athletic/academic event, death
in the family.) 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 you to take the
exam.
Homework
Relevant
homework problems from the textbook are listed below. 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.
| Chapter 1
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25, 26, 30, 31, 33, 38, 49, 52
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Chapter 2
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27, 32, 34, 35, 37, 40, 43, 53, 56
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Chapter 3
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30, 38, 42, 48
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Chapter 4
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25, 31, 34, 40, 48, 52, 54
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Chapter 5
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21, 22, 23, 30, 38
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Chapter 6
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23, 26, 28, 30, 31, 36, 39, 42, 44, 47, 48, 53, 58
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Chapter 7
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25, 26cd, 28, 38, 42, 43(not c), 46, 55, 56
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Chapter 8
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18, 19, 22, 23, 24, 28, 31, 35, 35, 41, 45
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Chapter 9
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31, 33, 37, 39, 44, 45, 50, 52, 61, 63, 64, 72, 77,
81, 82
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Chapter 10
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17, 18, 21, 23cefg, 25, 278, 30, 32, 36, 37
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Chapter 11
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25, 28, 30, 34, 36, 38, 41, 45, 47, 52, 56, 58, 64
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Chapter 12
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14, 21, 32, 34, 44
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Chapter 13
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32, 36, 37, 38, 42, 44, 46, 49, 50, 52, 53, 57, 66,
67
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Chapter 14
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20, 24, 27, 32, 36, 40, 43, 50, 55, 58
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Chapter 15
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18, 20, 25, 32, 33, 36, 45, 46
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These are the minimum number of
homework problems I would expect every student to work out. If you are having
difficulties, you should try additional problems in the textbook, look in the
Klein book, find any other textbook, or consult the Internet. For example, the
web site associated with the textbook has a multiple choice quiz for each
chapter.
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: Wednesday February 9, 2008
Section 2. Chapters 5,7,8
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 9, 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 6, 2008
Section 4. Chapters 12-14
IR and Mass spectroscopy, NMR spectroscopy, Problem Solving, Conjugated dienes
Exam 4: Monday April 25,
2008
Section 5. Chapter 15
Aromaticity: naming, rules, ions, heterocycles,
polycycles, spectroscopy,
Course Review
Comprehensive Final Exam: Monday May 9, 12:00pm
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 disregard
any rumors regarding how difficult this course is. Many students perform very
well in this class. 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!
Fourth,
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.
Fifth, 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, Michael Cammarata, will be available at
scheduled office hours. I am available at office hours and by appointment and
at help sessions. There is no excuse for not taking advantage of these
resources being made available to you. I am that principle resource! You cannot
come to too many office hours or make too many appointments. I am here for
you. 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.
Be sure to consult the
class web site for interactive molecules and ancillary materials that can be
helpful in learning organic chemistry.
Useful Web sites:
Handouts
Test answers
Quiz answers
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