CH 241: Organic Chemistry

Syllabus and Course Information - Fall 2001

Instructor: Dasan M. Thamattoor
Office: Keyes 302; Phone: 3429
Email: [email protected]
Materials:(a) "Organic Chemistry" by Maitland Jones, Jr., 2 nd Edition, Norton and Co., 2000. (Required)
(b) "Organic Chemistry Study Guide and Solutions Manual" by Henry L. Gingrich and Maitland Jones, Jr., Norton and Co., 2000. (Required)
(c) "ChemOffice Ltd." software from CambridgeSoft ( (Optional)
(d) "Molecular Model Set for General and Organic Chemistry" Prentice Hall, 1965. (Optional)
(Olin 1)
Three times a week (MWF 10:00 ­ 10:50 am). It is vital that you listen carefully to the lectures and write down good notes. These notes, and corresponding segments from the text, will be important resources to learn the material and prepare for exams. Occasionally, the detail with which a topic is covered in the text and lecture may not be the same.
(Keyes 305)
You have been assigned to one of five sections. Each section is about four hours long. Laboratory instruction will be provided by Jean McIntyre (four sections) and Das Thamattoor (one section). Your overall lab performance will be worth 20% of the course grade. Additional details are given in the accompanying handout. Questions concerning lab schedules, grading, etc. should be directed to Ms. McIntyre.
As announced in class each week and by appointment. Please try to make an appointment if you are unable to attend the scheduled office hours.
In addition to office hours, there will be help sessions scheduled about once every week. Time and venue will be announced in class.
Problem sets will be posted on the web at each week. The corresponding answer keys will be available the following week on the web and the Olin Science Library reserve desk. These problem sets will not be collected and graded. However, please resist the urge to look up answer keys without working out the problems first. The end-of­chapter problems are particularly important and it is in your interest to work out as many of them as possible.
Grading: There will be three fifty-minute "hour" exams during the regular class period and a cumulative two-hour final exam. Make-up exams are not available. All exams are closed-book and model sets are prohibited. Exam dates and point values are given below.
Exam 1: 100 points Monday, October 1 10:00 -10:50 am
Exam 2: 100 points Friday, October 26 10:00 - 10:50 am
Exam 3: 100 points Monday, November 20 10:00 - 10:50 am
Final: 150 points TBA
Lab: 100 points
Your total score in the course (out of 500 points) will be calculated using the two methods given below. The formula that gives you the higher score will determine your course grade.

Formula I: Two "best" hour exam scores + one half of remaining hour exam score + final exam score + lab score.

Formula II: All three hour exam scores + two-thirds of final exam score + lab score.

The chemistry department has a policy regarding attendance and missed exams that will apply to this course. Please familiarize yourself with these policies that are posted on the chemistry department web site at

Resources: Room 142 in the Olin science library has a number of organic chemistry texts, relevant to lecture and lab, available for your use. This room is well suited for group study and is equipped with a blackboard that you may use to work out problems. Answers to problem sets and exams will be placed on reserve at the circulation desk. Furthermore, course-related information may be downloaded from the web Free tutorial help will be provided to you if necessary. The number of tutors available, however, is limited. Please consult Ms. McIntyre if you think you need a tutor.
Topics of
The approximate order of topics to be covered is given below.
  • Atoms, molecules, bonding, polar and nonpolar molecules, intermolecular forces, solubilities, Lewis structures, preliminary ideas of resonance, arrow formalism, acids and bases.

  • Introduction to orbitals, molecular orbital description of bonding, hybridization, structure of methane.

  • Alkanes- conformational analysis, structural isomerism and nomenclature, alkyl groups.

  • Alkenes- structure and bonding, nomenclature, E-Z notation, hydrogenation, relative stabilities. Alkynes- structure and bonding, relative stabilities, double and triple bonds in rings.

  • Dienes and the allyl system, conjugation, introduction to the concept of aromaticity. UV spectroscopy.

  • Stereochemistry- chirality, enantiomerism, R-S notation, diastereomerism, optical resolution.

  • Ring systems- strain, stereochemistry of cyclohexane, conformational analysis of cyclohexane and its substituted derivatives, bicyclic and polycyclic compounds.

  • Nuclear Magnetic Resonance (NMR) spectroscopy.

  • Infrared (IR) spectroscopy.

  • Alkyl halides, substitution reactions of alkyl halides- SN 2 and SN 1 mechanisms. Elimination reactions- E1 and E2 mechanisms.

  • Overview of substitution and elimination reactions, oxidation of alcohols, rates and equilibria, syntheses.

  • Acids and bases revisited. Additions to alkenes- mechanism of hydrogen halide additions, regiochemistry, resonance effects, carbocation stabilities, addition of other unsymmetrical reagents, hydroboration, dimerization and polymerization of alkenes.

  • Carbocation rearrangements, addition of halogens to alkenes, oxymercuration, epoxidation and chemistry of oxiranes, cyclopropanation, carbenes, ozonolysis, alkene oxidations with permanganate and osmium tetroxide, addition reactions of alkynes.
Some Advice:There are over sixty students enrolled in the course this year. Surely each of you will have your own way of learning the material and I cannot prescribe a single method that will work for everybody. Nonetheless, based on my observations of students in past organic chemistry courses, I think a few common remarks can be made. Below, I share with you some of my thoughts on how you can do well in this course.
  • Please stay current with the material. The course is highly cumulative. Ideas introduced early on will be used to develop other concepts later. Thus, letting things slide is unwise, as the material begins to accumulate relentlessly. As the semester progresses and other demands on your time increase, playing catch-up will be harder to do. Furthermore, it is possible, indeed likely, that many of the concepts in the course will become clear only after you have had a chance to ponder them for a while. This period of reflection is critical and hence the need for time. So try not to learn everything at once. Even a half-hour of regular study each day is likely to be more useful to you than any all-night, caffeine-powered cramathons.

  • Write, write, write. I cannot overemphasize the importance of writing in this course. Simply listening to me lecture, reading your text, or watching ³cool² graphics flash by the screen is not enough. Sometimes it is all too easy to lull yourself into thinking that you understand the material. You will notice, however, that expressing your ideas clearly in writing (which is what you will have to do in the exams anyway) requires a higher level of mastery. To reach that level you must practice writing. Also, donıt try to work problems in your head. Write them out. Having the material written out in front of you often provides clues to solutions that you might not ³see² otherwise. So, please! Trust me on this. Write, write, write. Honest!

  • Network with your classmates. Obviously this advice is not going to work for everyone since some people prefer to study alone. Thatıs okay. Nevertheless, if you can, try studying with a partner or in groups. You will be astonished at the insight that you gain when you have to explain something to others. Besides, if each member of the group agrees to work a few problems, then the group as a whole will be able to work a large number of problems. Working as many problems as you can will greatly aid your understanding of the material. It is important, however, for all members of the group to be good citizens. One reason for the breakdown of group study is that one or two people do all the work and the rest just piggy-back. Donıt let that happen.

  • Make the most of the resources available to you. We are here to help you learn. So come talk to us. Itıs crazy not to take advantage of what we might have to offer by way of assistance. Office hours, help sessions, and personal; appointments are all excellent forums to ask questions. If the course does not seem to be going well, please get help right away. Our chances of rescuing you are better the more lead time we have.

  • Stay involved and keep a positive attitude. Perseverance will be an important key to success. Yes, it is a hard course but, no, it is not impossible. It can, in fact, be a lot of fun if you give it a chance. No kidding. Try it.

Welcome to the course, and good luck!