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CH343, Organic Chemistry 2,Spring 2010

Instructor: / Dr. Bruce Hathaway
Office: / Rhodes Hall 201E
Phone: / 651-2370
e-mail: /
Web Page: /
Office Hours: / MWF 9-10:30AM, and by appointment.
Lecture: / MWF at 11AM
Textbook: / Organic Chemistry, by Wade, 6th Edition, Prentice Hall.
Download: / ACDLabs freeware program ChemSketch, from
We will use this some in lecture and lab.
Assignments / Value / Grading scale:
Homework / 10% / A / 89-100%
4 Hour Exams / 72% (18% each) / B / 78-88.9%
Final Exam / 18% / C / 67-77.9%
D / 56-66.9%
F / <56%

Course Philosophy and Operation:

This course builds on Organic Chemistry 1, and I assume you have a good grasp of the fundamentals of naming, physical properties, reactions, mechanisms, and syntheses of the common functional groups. If you do not, you will need to work harder to catch up on what you don’t remember from Organic 1, as well as learn the new material in Organic 2.

When I lecture, I will focus on those things in each chapter which I think are the hardest to understand, and will try to present alternate explanations and examples to those in the book. Just because I don’t spend much time on something doesn’t mean I don’t think it is important. It may just mean the book does a good job of explaining that topic. Please feel free to come by and see me if you’re having trouble understanding something. I am always available during office hours. I am usually around during the day when I am not in class, either in my office or in my research lab (MG211).

I use a combination of tradition chalkboard lecturing, handouts, and PowerPoint presentations. You are responsible for downloading and printing off the PowerPoints yourself, it you want to use them in class. PowerPoints are available from the course website. Please do not post them on other websites, since I have done a lot of work to prepare them, and some contain copyrighted material.

Homework:The main goal of homework is to help you learn. Homework will be assigned and collected regularly. Turn in homework in the appropriate box in MG216. Late homework will be penalized 20% if it is turned by 9AM the next school day after the due date, and is not accepted after that.

Exams:There will be four in-class examinations on the dates indicated in the schedule. Since the subject is cumulative, you will need to remember previous material to do well on each exam. If you have to miss an exam for some legitimate reason, you must contact me beforehand, if at all possible, and I will arrange for a make-up exam. Your excused absence will have to be substantiated in order for you to make up the exam.

You may elect to rework any or all of the problems you missed on one hour exam this semester. If you rework a problem, and get the answer correct, you can earn one-half of the points you missed on that problem. For example, if you completely missed a 6-point problem, and rework it and get it correct, you can earn back 3 points. If you missed 4 points of a 6-point problem, and get it correct, you can earn back 2 points. You only get to rework the problems on one hour exam this semester, so you need to decide if you are going to do it on this exam, or save this opportunity for later.

Rules for Reworking an Exam.

  1. Do not write on your original exam!
  2. Rework your missed problems on separate sheets of paper, and staple them to the front of the exam.
  3. The reworked exams are due at the beginning of the next class period after the exams are returned to you. For example, if I return an exam on Monday, your work is due the next Wednesday at the beginning of class. No late papers will be accepted! If you are not here to pick up your exam, you need to come by my office and get it.
  4. True-False and multiple-choice questions must be explained to receive credit.
  5. Again, you can only rework one hour exam this semester.
  6. You can not rework the final exam.
  7. I will post keys to the exams within two days after people turn in their reworked exams.

Final Exam:The final exam will be Wednesday, May 12, at 10:00 AM. This will be a comprehensive exam worth 18% of the overall grade in the course.

Study Hints:

Organic Chemistry is cumulative. You have to keep up with the material. It is helpful to read the chapters before I lecture on them, just to get familiar with the vocabulary. Review your lecture notes as soon as possible after lecture to make sure they make sense. Read through the chapter again, working problems as you go. THE BEST WAY TO LEARN ORGANIC CHEMISTRY IS TO WORK PROBLEMS! When you have finished reading through the chapter, work as many of the end-of chapter problems as you can.

Preparation a Reaction Notebook: A Study Hint from the Journal of Chemical Education

(J. J. Esteb, J. R. Magers, L. McNulty, and A. M. Wilson, J. Chem. Educ.2006, 83(12), 1807-8)

Section 1: The Forward Reactions

This is a section of the reactions of each functional group (alkenes, alcohols, etc). There are tables at the end of each chapter which summarize these. Organizing reactions by similar mechanisms also helps. I’d encourage you to do a generic example, followed by a real example or two, such as the following for the reaction of a methyl halide with a strong nucleophile (SN2).

Section 2: The Common Product Section.

This is where you list all the ways to make a particular functional group. This will help you as you do synthesis. For example, there are two ways to make alkenes that we covered in chapter 7:

Do this for all of the reactions you learned in Organic 1, as well as Organic 2. It should help you organize our chemistry better than reaction flash cards.

Section 3: The carbon–carbon bond forming reaction section.

Make a separate section for C-C bond forming reactions, and their variations. You’ll use these alot!

Academic Honesty

I do not tolerate academic dishonesty in my classes. This includes, for example, cheating in any form on an exam, giving information to another student about an exam, seeking to obtain information from another student about an exam, and using another’s work and claiming it to be your own. Each instance of academic dishonesty will receive a grade of ZERO. See the academic honesty policy in the Undergraduate Bulletin for more details.

Classroom Etiquette

1. Please be on time. If you come in late, find a seat quickly without disturbing the class.

2. Please turn off or silence your cell phone and other electronic devices. Don’t take calls or make calls in class.

3. Personally, I find it irritating when I see people texting in class. Whether you mean it or not, it tells me that you think what I am trying to do is less important than keeping in touch with someone. Don’t do it.

4. Similarly, carrying on conversations with other students during class is distracting to me and to others, so please don’t do it.

RevisedSchedule of Topics

Dates / Topic / Chaps & Sections in Wade
What is it? Introduction to Spectroscopy
January 20, 22 / Introduction to CH343, Mass Spectrometry / Chap 12 sec 13 -15
January 25, 27, 29, February 1, 3 / Proton & Carbon NMR Spectroscopy / Chap 13
February 5, 8 / Infrared Spectroscopy / Chap 12, sec 1-12
February 10 / Nomenclature Review, Bicyclic Nomenclature / Chap 3.16, Chap 7.7E
February 12 / Problem Day: Bring your textbook!
Mon., Feb. 15 / Exam 1
Organometallic Carbon-Carbon Bond-Forming Reactions, & Thiol and Epoxide Chemistry
February 17, 19, 22 / Free-Radical Halogenation / Chap 4 and 6.6
February 24, 26 / Organometallic Compounds, Grignard Reactions / Chap 10.8-10; 14.15; 20.8; 21.9
March 1 /

Organolithium and Organocopper Reagents

/ Chap 10.8B; Problem 10-21; Chap 18-9
March 3, 5 /

Thiols and Epoxides

/ Chap 10.9E,12;
Chap 14.3C,11-16
March 8 / Review
Wed., Mar. 10 / Exam 2: Organometallic Reactions, Thiol and Epoxide Chemistry
Making Alkenes, and Additional Alkene, Alkyne, and Amine Chemistry
March 12 /

Wittig Reaction, Diels-Alder Reaction

/ Chap 18.13; 15.11
March 15, 17, 19 /

Spring Break

March 22, 24 / Wittig Reaction,Diels-Alder Reaction / Chap 18.13; 15.11
March 26, 29 / Additional Alkene Addition Reactions / Chap 8.3B, 5, 6, 7, 11-16
March 31 / Additional Alkyne Addition Reactions / Chap 9.9-10
April 2 /

“Designated Holiday” aka Good Friday

April 5, 7 /

Reactions of Arene Diazonium Salts & Synthesis of Amines

/ Chap 19.17-21
April 9 / Problem Day: Bring your textbook!
Mon. April 12 / Exam 3: Wittig, Diels-Alder, Alkenes, Alkynes, and Amine Chemistry
Making Big Molecules
April 14, 16 / Enol and Enolates of Aldehydes and Ketones / 22.1-11
April 19, 21 / Ester Enolate Chemistry / 22.12-17
April 23, 26 / Conjugate Addition and Robinson Annelation / 22.18-19
April 28 / Fatty Acid Biosynthesis / Handout
April 30 / Problem Day: Bring your textbook!
Mon. May 3 / Exam 4: Chapter 22
May 5, 7 / Nucleophilic Aromatic Substitution, Synthesis Example Problems / 17.12, handouts

Comprehensive Final Exam: Wednesday, May 12, 10AM