Douglass F. Taber . . . U. of Delaware

Home Page: Taber home page.

C 331

Organic Chemistry Lecture

M-W-F, 10:10-11:00

101 BRL

D. F. Taber Office Hours:

202 LDL M 11:00-1:00

831-2433 Friday 3:00-4:00

Fax: 831-6335

I will be glad to schedule other appointments if additional help is needed. I can be reached at Douglass F. Taber. There is also an optional help session with the TA's from 4:30-5:30 Tuesdays in 101 BRL. I will not talk with you about the course on the day of the exam.

When feasible, send your questions to me by email. I can then send the question and the answer to the whole class.

We will use electronic clickers to register responses in class. You are best served by participating, as instruction/coaching is based largely on this feedback from the class.

It is most effective to recruit a study buddy. Learning organic chemistry is like learning a new language. It is best accomplished by practicing with someone else. Note that years of old homework and answers and old exams and answers are on this website. For each homework, you and your buddy each choose a different older homework of that number. Work through yours, then swap, and grade each other rigorously, following the posted key. Then, explain to your study buddy what he did wrong, and how to do it correctly. Repeat the process with another older homework of that same number, until you are doing well - then do the current homework on your own, and turn it in. Use the same procedure to prepare for each exam. This is by far the best way to make sure as you go along that you really know the material. Tutors are also available, individually, or, if at least six people sign on, tutoring is free through Academic Services.

Texts: Organic Chemistry, Vollhardt & Schore, 5th Ed.

Organic Chemistry Study Guide, Schore

Molecular Model Set

Grading: There will be three hour exams and a final. The four exams will be of equal value, totaling 90% of the grade. All exams will be open book and open notes. In addition, there will be weekly homework assignments, that will together count 9% of the grade. The HW sets are each worth 30 points, but if you earn even one point, you receive all 30 points in the gradebook. You should approach these HW sets individually, after preparing by studying together. Make sure that you understand the material - you will be on your own on the exams. Participation in online course evaluation is worth 1% of the grade.

Schedule: Hour Exams Friday Sep. 26, Friday Oct. 24th, Friday. Nov. 21st. The Wednesday immediately preceding each Friday exam will be a review session. There will also be a review session before the final exam. The final exam will be two hours.

The emphasis this semester will be on learning the basic mechanisms of organic chemistry. These are covered in the first 13 chapters of Vollhardt and Schore, excluding Chapter 10, and Chapter 17. We will also cover the IUPAC system of Organic Nomenclature.

You will be responsible in the homework and on the exams for all material covered in the lecture and on the website.

There are four classes of mechanisms you will need to master this semester:

1. Free radical

2. Nucleophilic anionic

3. Acid catalyzed

4. Sigmatropic rearrangement

We will also cover:

Shapes of organic molecules

Nomenclature of organic molecules

Organic spectroscopy

Synthesis

History of Organic Chemistry: The history of the development of organic chemistry is fascinating. We will touch on it briefly. For further background, Morris Library has Chasing the Molecule, by John Buckingham QD 461 .B83x. It is an interesting read.

Use of the textbook: Each week, reading will be assigned in the text. This is to be read before the week starts, as an introduction to the lecture material. You may find it helpful to highlight in the text the material that we cover in the lecture, as those are the parts of the text for which you will be responsible on the exam. The Table of Contents serves as a handy outline of topics. It is useful to note which are covered in lecture, and which are not.

Organizing the course material: Because the exams are open book and open notes, it is important that you develop a system for indexing your lecture notes so you can find that information that you need at the time that you need it. You may find it helpful to build a simple database to keep track of the information. Electronic devices are not to be used during the exam. Any electronic devices in use during the exam, including cell phones and calculators, will be confiscated and not returned.

Week 1: (Wednesday Sep 3rd) Chapter 1; pp. 68-69 of Chp. 2, and pp. 105-118 of Chp. 3

structure and bonding of organic compounds; organic functional groups; Lewis dot structures, hybridization, electronegativity; free radical halogenation

Homework #1 due Mon Sep 8th by 10 a.m. in 101 BRL. HW may also be faxed before 10 p.m. to 831-6335. Be sure to put my name on the fax.

Week 2: (Monday Sep. 8th) Chapter 2, Chapter 4, Chapter 5

free energy diagrams; IUPAC nomenclature

Fischer projections, Newman projections, R vs. S, diastereomers, enantiomers

Cyclohexane conformations - axial vs. equatorial

Handout on Energy and ratios.

Homework #2 due in 101 BRL before class Monday September 15th

Week 3: (Monday September 15th) Chapter 3, and also pp. 532-535, 579, 606-607, additional handout on website Bu3SnH.

homolytic vs. heterolytic; free-radical halogenation, bond-forming, bond-cleaving reactions; arrow-pushing mechanisms

Homework #3 due Monday Sept. 22nd

Week 4: (Monday September 22nd) Review for exam

Wednesday: Review for exam - being your questions!

Friday Sep. 26th Exam #1

Week 5: (Monday September 29th) Chapter 6

S_N2 reactions

Homework #4 due Mon Oct 6th

Week 6: (Monday October 6th) Chapter 7.1-7.6, 9.3

Acid-mediated mechanisms

Homework #5 due Mon Oct 13th

Week 7: (Monday October 13th) Arrow-pushing mechanisms, synthesis, structures and structural change from ¹³C NMR data.

Homework #6 due Mon. Oct 20th

Week 8: (Monday October 20th)

Wednesday: Review session - bring your questions!

Friday Oct 24th Exam #2

Week 9: (Monday October 27th) Chapters 7.6-7.8, 8, 9, 11

Careers in Chemistry and Chemical Engineering discussion

E₁, E₂ elimination; conformational analysis

Homework #7 due Mon Nov 3rd^th

Week 10: (Monday Nov 3rd) Alkene reactions Chapters 12, 17

hydride reductions, S_N2 reactions, nucleophilicity, acidity

Homework #8 due Mon. Nov 10th

Week 11: (Monday November 10th)

functional group interconversions, arrow-pushing mechanisms, stepwise synthesis, Grignard reactions

Homework #9 due Mon Nov 17th

Week 12: (Monday November 17th)

alkene additions, stepwise reactions, stereochemical reasoning

Wednesday: Review Session – bring your questions

Friday November 21st Exam #3

Week 13: (Monday Nov. 24th) Alkyne construction

Homework #10 due Monday Dec. 1st

Week 14: (Monday Nov. Dec. 1st) Chapter 13

alkene construction, Wittig reaction, alkyne chemistry; special handout: alkyne zipper.

Homework #11 due Mon. Dec. 8th

Week 15: (Monday December 8th) Review for final - last class Wednesday December 10th