Organic Chemistry I
Spring 2014

9:30 – 10:20 CSI 437

Instructor:Dr. Steven Bachrach
Office:CSI 370G
Office Hours:MWF 1:00-2:00pm or by appointment
HHMI Peer tutor:Helene Nepomuceno (
Office hours: TR 8-9:30pm
Help Sessions:Monday 5-6pm, CSI 441
Dr. Mills help session: Tuesday, 4:00-5:00 PM, CSI 104
Text:David R. Klein, Organic Chemistry (required)
Electronic access Sapling Learning Systems-Organic (required)
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, we will skip some sections). 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:
Online Molecular Structures:
Movies: SN2 reaction
SN1 reaction (first step)
Water symmetric stretch
Water asymmetric stretch
Water bend
Cyclopropane wag
In-class Assignment NMR problems (Chapter 16)

Your grade for the course will be based on your highest three exam scores (out of four), your online homework, and the final exam. Each exam is worth 100 points for a total of 300 possible points, all of the homework assignments collectively are worth 100 points, and the final exam is worth 150 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. 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.

Homework:100 points
Top 3 Exams:300 points
Finale Exam:150 points
Total:550 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.

We are using Sapling Learning for online homework this semester. There will be weekly homework assignments, except for weeks when we have an exam. Each homework set will have 12-25 problems, so expect to take an hour or two (maybe more) to complete each assignment. They do not have to be completed in one sitting. If you get a wrong answer you can try again, often with some hints, but each additional answer will be docked some points. You can use your textbook while doing the online homework, but you must work alone.

You may wish to do additional homework problems. The end of each chapter of our textbook has additional problems. You might even want to do a few of these before going online. Please seek help from me or Helene at office hours, help sessions or by appointments for assistance with the homework!

Additional suggested problems

163, 66
261, 66
352, 56, 61
464, 67, 69
553, 58, 60
650, 53, 54
766, 68, 69, 73
882, 83, 85, 87
973, 74, 81, 82
1665, 67
Sapling Learning Instructions

1. Go to

2a. If you already have a Sapling Learning account, log in and skip to step 3.
2b. If you have Facebook account, you can use it to quickly create a SaplingLearning account. Click the blue button with the Facebook symbol on it (just to the left of the username field). The form will auto-fill with information from your Facebook account (you may need to log into Facebook in the popup window first). Choose a password and timezone, accept the site policy agreement, and click "Create my new account". You can then skip to step 3.
2c. Otherwise, click "create account”. Supply the requested information and click "Create my new account". Check your email (and spam filter) for a message from Sapling Learning and click on the link provided in that email.

3. Find your course in the list (you may need to expand the subject and term categories) and click the link.

4. Select a payment option and follow the remaining instructions.

5. Work on the Sapling Learning training materials. The activities, videos, and information pages will familiarize you with the Sapling Learning user environment and serve as tutorials for efficiently drawing molecules, stereochemistry, etc. within the Sapling Learning answer modules. These training materials are already accessible in your Sapling Learning course.

Once you have registered and enrolled, you can log in at any time to complete or review your homework assignments. During sign up - and throughout the term - if you have any technical problems or grading issues, send an email to explaining the issue. The Sapling support team is almost always more able (and faster) to resolve issues than your instructor.

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




Jan 15

Lewis structures, formal charge, atomic orbitals, hybridization, dipoles, intermolecular interactions, molecular representations



Jan 20

molecular representations, resonance


Jan 27

Acids and bases, alkane nomenclature

3, 4.1-4.2

Feb 3

Alkane isomers, conformations, cycloalkanes


Feb 10

Stereoisomers, chirality, optical activity

Feb 12 Exam 1


Feb 17

Thermodynamcis, equilibria, kinetics, mechanisms and arrow pushing


Feb 24

Alkyl halides, substitution reactions, SN1, SN2


Mar 3

Alkenes, nomenclature, elimination reactions, substitution vs, elimination


Mar 10

Spring break


Mar 17

Introduction to addition reactions

Mar 19 Exam 2


Mar 24

Addition reactions, multistep synthesis


Mar 31

Alkynes, nomenclature preparation and reactions


Apr 7

Spectroscopy, NMR

Apr 11 Exam 3


Apr 14

IR spectroscopy, synthesis

15.2-15.7, 12

Apr 21

Alcohols, nomenclature preparation


Apr 28

Ethers and expoxides, nomenclature

Apr 30 Exam 4



May 10, noon, Final Exam


Exam Schedule

            Exam 1: February 12

            Exam 2: March 19

            Exam 3: April 11

            Exam 4: April 30

            Comprehensive Final Exam: Saturday May 10, noon

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, working through lots of homework problems is essential. There will be weekly graded homework assignments handled through the Sapling Learning online tool. Additional problems can be found at the end of every chapter. You might want to try a few homework problems from the textbook before doing the online homework sets.  You will learn by struggling through a problem yourself but do not hesitate to seek help from me or the peer tutor. I have access to the online system and I am happy to look over your online work and use this to help identify where you are having troubles. 

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, Helene Nepomuceno, 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 can be 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.

One can find a lot of very useful information on the internet, including Wikipedia. I have found some really useful places for advice for students starting organic chemistry:

Posts on the Master Organic Chemistry Blog can be very helpful in providing yet another perspective on concepts in organic chemistry.

Exam answer key