Chem 220A: Section 2

Organic Chemistry Lecture (Fall 2002)

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

SC 4309

Carmelo J. Rizzo

office: SC 7662

Tel.: 322-6100


Click here for C. J. Rizzo's Chem 220b and Chem 220c pages.

You will need Adobe Acobat Reader 4.0 to view pdf files.


Questions & Answers Page: I am posting questions and answers from the class, sent to me via email.


*** Overall Class Distribution ***



Required text: Organic Chemistry, 5th edition, John McMurry

Study Guide and Solutions Manual for Organic Chemistry, 5th Ed., Susan McMurry )


Other Optional Study Guides (available in the Bookstore):

Organic Chemistry, 2nd Ed. (Schaum Outline Series)
3000 Solved Problems in Organic Chemistry (Schaum's Solved Problem Series)
Organic Chemistry (REA Problem Solvers)


Lab Text (required): The Organic Chem Lab Survival Manual, J. W. Zubrick
Class pak (Campus Copy)
Laboratory Notebook (Hayden-McNeil)
Safety Goggles


Molecular Models: Organic chemistry is a three dimensional science. Molecular models are highly recommended for lecture and may be purchased from the Student Affiliates of the American Chemical Society:

Organic Chemistry Models (Molecular Design, Inc.) $25.00

Office Hours: M, W: 11:00-12:00 am; T, R: 10:00 am-11:00 noon and by appointment. Office hours are subject to change or cancellation without prior announcement.

Course Content: Chapters 1-14 of McMurry, see following.

Course Policies:

Exams: 3 seventy-five minute exams (100 points each)

1 two-hour final exam (150 points)

The final grades will be determined as follows:

Three Exams (67% of final grade)

Two-hour final Exam (33% of final grade)

Grades: 90-100= A range; 80-89= B range; 70-79= C range; 60-69= D range; below 60= F

Exam dates are indicated on the accompanying schedule and will NOT be changed.

Final Exam: The final exam date is Sat. Dec. 21 at 9:00-11:00 am in room SC 4309. There will be NO alternative date offered. Please make your travel plans accordingly.

Make Up Exams: I will give make-up exams under the following conditions:

1. If it can be made up before the next scheduled class period.
2. If it is arranged prior to the day of the missed exam.
3. There is a legitimate medical or family excuse. These excuses must be verified in writing by the Dean's office for family reasons or a physician for illness. A note stating that you visited Student Health is not sufficient. Having other exams on the same day nor anxiety attacks will not be considered.

If all three of these condition cannot be met and you have an excusable absence from the exam then your final exam will count for a proportionally larger portion of the total grade. It is to your advantage to take all exams.

A note on partial credit: Simply writing down an answer does not entitle you to partial credit. The answer must first be at least partially correct; second, it must be relevant to the question being asked. Writing down the answer to a question that is not being asked does not warrant partial credit.

Honor Pledge: You must legibly write the Vanderbilt Honor Pledge on every exam. Writing the honor pledge acknowledges that you are committed to it. Exams which do not have the honor pledge will not be graded and you will receive a zero.

A Helpful Hint: There is a tremendous volume of information to be covered in this course and we will need to proceed at a brisk pace. I suggest that you come to class prepared, having already read the chapter. This will allow you to concentrate on concepts that may be unclear to you. Chemistry is a problem solving oriented subject, thus I suggest that you try every problem in the chapters we cover ( you may see some of them reappear on exams). Finally, come to class !! Important concepts, i.e. thing that may appear on exams, are emphasized in lecture as well as things not covered in the book. This course is challenging; be prepared to dedicate at least 2 hours per night (10 hrs/wk) on organic chemistry.

Letters of Recommendation: I am willing to write you a honest letters of recommendation. Request for letters should be made to me preferably one month before they are due. Requests for letters for early admissions to Vanderbilt Medical School must be made before Spring Break.

Review from General Chemistry: It is assumed that you have mastered the material taught in General Chemistry. In particular, please review the following topics.

Text: "Chemistry: Science of Change", 3rd ed.; Oxtoby, Freeman & Block
Saunders College Publishing: 1998

Electronic Structure Chapter:17-1
Chemical Bonds 17-4 through 17-6
Atomic Orbitals 16-5
Molecular Orbitals 18-1 through 18-5
Lewis Structure 3-4, 3-5
Chemical Equilibrium 7-1, 7-2, 7-5
Acid-Base Equilibrium 8-1 through 8-4
Thermochemistry 10-2 through 10-5, 11-5 through 11-8

As the course progresses there will be some important numbers and equations you will be expected to commit to memory. These will be explicitly pointed out to you. You should already know the following from General Chemistry.

The Gas Law Constant, R= 1.99 cals/(mol)(°K) (2.0 is close enough) -or- = 8.314 J/(mol)(°K)

Gibb's Free Energy: DG°= DH° - TDS°

DG°= -RT ln Keq

pKa= - log Ka

In addition, it is also assumed that you know the vocabulary of General Chemistry. That is, you should know the names, structures and charges of the common anions (see Table 3-2, pg. 84 of Oxtoby, Freeman& Block) and the names and structures of common mineral acids (see Table 4-2, pg. 138 of Oxtoby, Freeman& Block) and bases.

Tentative Class Schedule



 Links to Handouts or Comments
Wed  Aug 28  Chapter 1: Structure and Bonding  Chapter 1 Slides (revised)
Fri Aug 30 Chapter 1 (con't)
Mon Sept 2 Chapter 2: Polar Bonds and Their Consequences Chapter 2 Slides
Wed Sept 4 Chapter 2 (con't)

 Drawing Chemical Structure

Curved Arrow Convention

Fri Sept 6 Chapter 3: Organic Compounds: Alkanes and Cycloalkanes  Chapter 3 Slides (updated)
Mon Sept 9 Chapter 3 (con't)

 Naming Alkanes

Naming Cycloalkanes

Wed Sept 11 Chapter 3 (con't)

n-Hexane (Chem3D) (Powerpoint )

Cyclohexane (Chem3D) (Powerpoint)

Fri Sept 13

Chapter 4: Stereochemistry of Alkanes and


 Chapter 4 slides (revised)
Mon Sept 16  Chapter 4 (con't)

 ethane (Chem3D) (Powerpoint) (animated gif)

propane (Chem3D) (Powerpoint) (animated gif)

butane (Chem3D) (Powerpoint) (animated gif)

Wed Sept 18  Chapter 4 (con't)

 Ring Strain

Chair-Chair Interconversion of cyclohexane (animated gif)

Energetics of the chair-chair interconversion
(courtesy of Dr. Ian Hunt, Univ of Calgary)
Fri Sept 20  EXAM 1: CHAPTERS 1-4

 Exam 1 answers ,

approximate grade distibution for Exam 1

Mon Sept 23 Chapter 5: An Overview of Organic Reactions  Chapter 5 slides
Wed Sept 25 Chapter 5 (con't)  The Curved Arrow Convention
Fri Sept 27  Chapter 5 (con't)  
 Mon Sept 30  Chapter 6: Alkenes: Structure and Reactivity  Chapter 6 Slides
 Wed Oct 2  Chapter 6 (con't)

 Naming Alkenes

The Cahn, Ingold Prelog Convention

 Fri Oct. 4  Chapter 6 (con't), QUIZ 1 (Chapters 5 and 6)  Quiz 1 answers , average
 Mon  Oct. 7  Chapter 7: Alkenes: Reactions and Synthesis  Chapter 7 Slides
Wed Oct 9  Chapter 7 (con't)


Reactions of Alkenes

 Fri Oct 11 Chapter 7 (con't)  
 Mon Oct 14 Chapter 8: Alkynes: Reactions and Synthesis  Chapter 8 Slides
Wed Oct 16  EXAM 2: CHAPTER 1-7

 Mid-semester Progress Reports Due

Exam 2 answers

approximate grade distibution for Exam 2

 Fri Oct 18 Chapter 8 (con't)

Reactions of Alkynes

Similar reactions of Alkenes and Alkynes



Oct 21-22 October Break- No Classes  
Wed  Oct 23  Chapter 9: Stereochemistry  Chapter 9 Slides (updated 10/26)
 Fri  Oct 25  Chapter 9 (con't)  Some Organic Synthesis Problems (answers)
 Mon Oct 28 Chapter 9 (con't)

 The Cahn, Ingold, Prelog Convention 

Absolute Configuration

Wed Oct 30  Chapter 10: Alkyl Halides (answers) Chapter 10 Slides
 Fri Nov 1 Chapter 10 (con't), QUIZ 2

 Quiz 2 answers , average

Overall Class Distribution

 Mon Nov 4 Chapter 10 (con't)

Drawing Chemical Structure 

Reactions of Alkyl Halides

 Wed Nov 6 Chapter 11: Reactions of Alkyl Halides: Nucleophilic Substitution and Eliminations  Chapter 11 Slides
 Fri Nov 8 Chapter 11 (con't)  SN1 vs. SN2
 Mon Nov 11 Chapter 11 (con't)  
 Wed Nov 13  Chapter 12: Structure Determination: Mass Spectrometry and Infrared Spectroscopy   Chapter 12 Slides
 Fri Nov 14 Exam 3: Chapters 1-11

Exam 3 answers

approximate grade distibution for Exam 3

 Mon Nov 18 Chapter 12 (con't)  Table of Exact Masses
 Wed Nov 20  Chapter 12 (con't)

 Typical IR absorptions

animation of an IR strecthing frequency

Hooke's Law animation

(courtesy of Dr. Ian Hunt, Univ of Calgary)

 Fri Nov 22  Chapter 13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy  Chapter 13 slides (updated)

Nov 25-29
 Fall Break (no classes)  
 Mon Dec 2 Chapter 13 (con't)

Basic NMR concepts and animations

NMR Web Lecture with animiations

pulsed NMR animations

more pulsed NMR animations

(you need the Shockwave plug-in to view these)

 Wed Dec 4 Chapter 13 (con't)

 Typical 1H and 13C NMR shifts 

Shoolery's Rules

Solving Combined Spectra Problems

Some combined spectra problems (answers)

 Fri Dec 6 Chapter 14: Conjugate Dienes and Ultraviolet Spectroscopy Chapter 14 Slides
 Mon  Dec 9  Chapter 14 (con't)

 Diels-Alder Reaction 

Some Diels-Alder Animations

 Wed  Dec 11  Chapter 14 (con't)  
 Sat, Dec 21  Final Exam, 9:00 - 11:00 am, SC 4309: Chapters 1-14 Information that will be provided on the final exam

Suggested Problems: Listed are representative problems from each chapter. Organic Chemistry is a problem solving oriented course. It is suggested that you work all the problems in each chapter and more if possible. Working problems will enhance your ability to do well on exams.

Chapter 1 Problems: 1-6, 8-14, 16, 21-23, 25-28, 34, 37-41, 44-46

Chapter 2 Problems: 1-19, 21, 22, 25-31, 33, 34, 36, 38-47, 49-53, 55, 56

Chapter 3 Problems: 1-13, 16-20, 22, 23, 26-30, 33, 34, 37-40, 42-44, 46-4

Chapter 4 Problems: 1-19, 22, 23, 25-29, 32-35, 38-44, 52

Chapter 5 Problems: 1-15, 18-30, 37-40

Chapter 6 Problems: 1-22, 24-31, 35-42, 44, 46, 47, 49, 51, 52

Chapter 7 Problems: 1-16, 20-27, 30-33, 35, 38-44, 48, 49

Chapter 8 Problems: 1-26, 28-33, 36-41

Chapter 9 Problems: 2-27, 29-36, 41, 43-55, 58, 62, 64-66

Chapter 10 Problems: 1-17, 21-27, 29, 30, 32-37, 40

Chapter 11 Problems: 1-20, 25-28, 30-32, 35-40, 45-48, 52

Chapter 12 Problems: 3, 5-15, 29-37, 39, 41

Chapter 13 Problems: 3, 4, 6-23, 25, 27, 30-40, 42-54

Chapter 14 Problems: 1-6, 9-12, 15-19, 21, 26, 31-37, 40, 47, 50, 54


Exams from Fall 1997

Exam 1 (answers)
Quiz (answers)
Exam 2 (answers)
Quiz (answers)
organic synthesis problems (answers)
Exam 3 (answers)
Combine Spectroscopy Problems (answers)


Some Useful Links

Organic Chemistry OnLine Tutorial

Chemistry ConcepTests

Web-sters Organic Chemistry

Eductional Material for Organic Chemistry

IUPAC Nomenclature of Organic Chemistry

 Prentice-Hall Online Gallery

 Texas A&M Organic Chemistry Homepage

 Colby College Organic Chemistry Resource Page

 Links to other Organic Chemistry Study Guides

 Georgia State University- Organic Chemistry Resources Worldwide

 Electronic Flashcards of Organic Reactions

 How to Tackle Organic Syntheses Problems

 Organic Chemistry Related Links from BioChemNet