Chem 220B, Section 01

Organic Chemistry Lecture

Spring 2008

T,R 9:35-11:00 am

Room SC 4327

 Carmelo J. Rizzo

office: SC 7662

Tel.: 322-6100


Updated : 04/15/2008

Click here for C. J. Rizzo's Chem 220a page.

 You will need Adobe Acobat Reader to view pdf files.

The Final Exam will be held on Friday, April 25 from 9:00 - 11:00 am in room SC 4327. No alternative final exam will be offered. 

Office hours for the week of April 21:

Mon., April 21: 10:00 - 11:00 am

Tue., April 22: 11:00 - 12:00 am

Wed., April 23: 11:00 - 12:00 am and 1:00 -2:00 pm

Thur., April 24: 11:00 - 12:00 am and 1:00 -2:00 pm

Final Exam Reviews: Wed., April 23, from 5:00 - 6:00 pm in SC 4309 and Thur. April 24, from 5:30 - 6:30 pm in SC 4309

Questions & Answers Page: I am posting questions and answers from the class, sent to me via email. Updated (04/02/2008)


Required text: Organic Chemistry, 7th edition, Francis A. Carey (ISBN 978-0-07-304787-4)

Optional text: Student Solutions Manual to Accompany Organic Chemistry, Atkins & Carey

The text and study guide have been bundled by the bookstore.

Other Optional Study Guides (available in the Bookstore):

Organic Chemistry, 3rd Ed. (Schaum Outline Series)
3000 Solved Problems in Organic Chemistry (Schaum's Solved Problem Series)
Organic Chemistry (REA Problem Solvers)

You must be concurrently enrolled in Organic Chemistry Laboratory (Chem 219b) which is taught by Professor A. List. Please direct all question regarding the lab to Professor List. 

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.)

or from the Bookstore:

HGS Molecular Structure Models

Course Content: Chapters 13, 15-28 of Carey. A tentative schedule of topics is listed below. Chapters covered on the hour exams and Final may be adjusted if we fall behind schedule; the exams will never cover more than is stated.

Office Hours: M: 10:00-11:00 am; T: 11:00 am-12:00 am; W: 1:00 pm - 2:00 pm, and by appointment. Office hours are subject to change or cancellation without prior announcement. E-mail is an excellent way to communicate with me.

Weekly Review Session will be held as follows:

Monday, 7-8 pm in SC 4327 (M. Sulikowski)
Tuesday, 8-9 pm in the Towers Conference Room in the Commons Center (Michael Funk)
Thursday, 4:30-5:30 pm in SC 4309 (M. Sulikowski)

Course Policies:

Exams: Three hour exams (75 pts each), Three 15-min quizzes (25 pts each), and one two-hour final exam (100 pts)

Exam and quiz dates are indicated on the schedule below and will NOT be changed. Hour exams and quizzes will be given during the regularly scheduled class time. In addition to the three in-class quizzes, Dr. Sulikowski will be posting weekly on-line quizzes through OAK. At the end of the semester, your point total from the weekly on-line quizzes will be scaled to 25 pts (the same as an in-class quiz). The three best quiz scores will be used to calculate your final grade.

Final Exam: The final exam date is Fri., April 25, 2008 from 9:00-11:00 am in room SC 4327. There will be NO alternative date offered. Please make your travel plans accordingly.

Grades: Exams & Quizzes (75 % of final grade); Two-hour final Exam (25% of final grade)

Your final grade will be determined by your overall average according to the absolute scale shown below. The cutoffs may ultimately be expanded according to the class distribution.
90-100= A range; 80-89= B range; 70-79= C range; 60-69= D range; below 60= F

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

1. If it can be made up within 24 hrs of the missed exam.
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. There will be no make-up quizzes.

A note on partial credit: Simply writing down an answer does not entitle you to partial credit. For partial credit to be awarded 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.

Handing back of exams and re-grades of exams: The goal is to have the exams graded and returned by the next scheduled class. Requests for re-grade requests will be considered for one week after the day the exams are handed back. DO NOT MAKE ANY MARKS ON THE EXAMS UNTIL YOU ARE SATISFIED WITH THE GRADING!!

Honor Pledge: You must legibly write the Vanderbilt Honor Pledge on the cover sheet of every exam. Writing the honor pledge acknowledges that you are committed to the Vanderbilt Honor Code. 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 1-2 hours per night (5-10 hrs/wk) on organic chemistry.

Review of Previous Material: It is assumed that you have mastered the first semester of Organic Chemistry (Chapters 1-14 of McMurry) as well as understand the vocabulary of organic chemistry. Of particular importance, please review the chapters on NMR and IR spectroscopy. In addition to the material from Chem 220a, please review the following topics from General Chemistry.

Text: "Chemistry: Science of Change", 2nd ed.; Oxtoby, Nachtrieb & Freeman, Saunders College Publishing: 1994

Electronic Structure Chapter: 18-1
Chemical Bonds 18-4 through 18-6
VSEPR 18-6, 19-2
Atomic Orbitals 19-1
Molecular Orbitals 19-1, 19-2
Lewis Structure 3-4, 3-5
Chemical Equilibrium 8-1, 8-2, 8-5
Acid-Base Equilibrium 9-1 through 9-4
Thermochemistry 11-2 through 11-5, 12-5 through 12-8

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

You should also know the names, structures and charges of the common anions (see Table 3-2, pg. 84 of Oxtoby, Nachtrieb & Freeman) and the names and structures of common mineral acids (see Table 4-2, pg. 123 of Oxtoby, Nachtrieb & Freeman) and bases (see Table 4-3, pg. 125 of Oxtoby, Nachtrieb & Freeman).


Suggested Problems: Listed below 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.


Tentative Class Schedule



 Suggested Problems, Comments, and Links to Slides and Handouts

 Thur  Jan 10  Chapter 13: Spectroscopy  Problems: 3-19,21-24,27-37,41-43,52-57
 Tue  Jan 15  Chapter 13 (con't)

 Slides for Chapter 13, #1-73 (pdf / ppt)(updated 01/25/2008)

 Thur  Jan 17  Chapter 13 (con't)

 Typical NMR shifts and IR absorptions (updated 1/15/08)

  Tue  Jan 22  Chapter 13 (con't)

 Chapter 15.14

 Quiz on Chapters 13 (answers) (Quiz 1 distribution)

 Slides for Chapter 15.14, #74-78 (pdf / ppt)(01/16/2008)

 Problems: 15.17, 43-48


 Thur  Jan 24  Chapter 16: Ethers, Epoxides and Sulfides  Slides for Chapter 16, #79-96 (pdf / ppt)(updated 01/25/2008)

 Problems: 1, 3, 5-7, 9, 10, 12-17, 25-27, 29, 32-35, 40-43

 Tue  Jan 29  Chapter 17: Aldehydes and Ketones:  Nucleophilic Addition to the Carbonyl Group  Slides for Chapter 17, #97-125 (pdf / ppt)(01/23/2008)  

 Problems: 1-7, 9-11, 13-21, 25-28, 30-36, 40-43, 45-51

 Thur  Jan 31  Chapter 17 (con't)  Curved Arrow Convention
 Tue  Feb 5  EXAM 1 (answers) (Exam 1 distribution)  Chapters 13, 15-17
 Thur  Feb 7  Chapter 18: Enols and Enolates  Slides for Chapter 18, # 126-146 (pdf / ppt)

 Problems: 1-10, 13-15, 17, 19-23, 26-30, 33-35, 41, 43-48

 Tue  Feb 12  Chapter 18 (con't)

 Chapter 19: Carboxylic Acids

 Slides for Chapter 19, # 147-164 (pdf / ppt)

 Problems: 1-4, 7, 8, 11-17, 19-24, 30, 32-34

 Thur  Feb 14  Chapter 19 (con't)  
 Tue  Feb 19  Chapter 20: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution

  Quiz on Chapter 18-19 (answers) (Quiz 2 distribution)

 Slides for Chapter 20, # 165-190 (pdf / ppt)

 Problems: 1-8, 12, 13, 16-18, 20-25, 27, 28, 31-36, 40-42

 Thur  Feb 21  Chapter 20 (con't)


 Tue  Feb 26  Chapter 20 (con't)  
 Thur  Feb 28  EXAM 2 (answers) (Exam 2 distribution)  Chapters 13, 15-20
  Mar 3 - Mar 7
 Spring Break (no classes)  Mid-semester progress reports due
 Tue  Mar 11  Chapter 21 Ester Enolates  Slides for Chapter 21, #191-202 (pdf / ppt)

 Problems: 1-11, 13-17, 19-22, 24, 25, 30

 Thur  Mar 13  Chapter 22: Amines  Slides for Chapter 22, #203-227 (pdf / ppt)  

 Problems: 1-5, 6, 7, 9, 11-15, 18-25, 27-37, 39-42, 44, 45, 47, 48, 51, 52

 summary of electrophilic aromatic substitution and reactions of aryl diazonium ions .

  Synthetic applications of Enamines (pdf / ppt)  

 Tue  Mar 18 Chapter 23: Aryl Halides  Slides for Chapter 23, #228-233 (pdf / ppt)  

 Problems: 2, 3, 6, 9, 11-13, 15, 18, 19, 21, 26

 Thur  Mar 20  Chapter 24: Phenols

 Quiz on Chapters 21-22 (answers) (Quiz 3 distribution)

 Slides for Chapter 24, #234-245 (pdf / ppt)  

 Problems: 1, 3, 6-15, 17-22, 30

 Tue  Mar 25  Chapter 25: Carbohydrate  Slides for Chapter 25, #246-279 (revised 3/26/08) (pdf / ppt

 Problems: 1-8, 11-13, 15-25, 27-29, 33, 36, 38, 40-43

 Thur  Mar 27  Chapter 25: (con't)  Brief Review of Stereochemistry

 Fischer Projections

 Tue  Apr 1

 Chapter 25: (con't)

 Thur  Apr 3  EXAM 3 (answers) (Exam 3 distribution)  Chapters 13, 15-25
 Tue  Apr 8  Chapter 26: Lipids  Slides for Chapter 26, #280-306 (pdf / ppt)  

 Problems: 1, 3-6, 8-11, 17, 19, 22, 23, 24, 27, 31

 Thur  Apr 10  Chapter 27: Amino Acids,  Peptides, and Proteins  Slides for Chapter 27, #307-339 (pdf / ppt)  

 Problems: 1-7, 10-12, 15-24, 27, 28, 30, 33-37, 39, 40, 42

 Tue  Apr 15  Chapter 27: (con't)   
 Thur  Apr 17  Chapter 28: Nucleosides, Nucleotides and Nucleic Acids  Slides for Chapter 28, #340-365 (pdf / ppt)    

 Problems: 1, 4-6, 10, 12-15, 18, 20, 21, 24

 Tue  Apr. 22  Chapter 28: (con't)
 Fri  Apr 25   Final Exam, 9:00 - 11:00 am, SC 4327  Chapters 13, 15-28

Exams from 2006 (Text: McMurray, Organic Chemistry. 6th ed)

 Exam 1

 Exam 1 answers

 Exam 2

 Exam 2 answers

 Exam 3

 Exam 3 answers


Some Useful Links

Organic Chemistry OnLine Tutorial

Electronic Flashcards of Organic Reactions

Chemistry ConcepTests

Organic Structure Elucidation: A Workbook of Unkowns

Organic Chemistry Practice Problems

Web Spectra: Problems in NMR and IR  

IUPAC Nomenclature of Organic Chemistry

1H NMR Interpretation Tutorial

 Texas A&M Organic Chemistry Homepage

Structure Elucidation by 1H and 13C NMR 

Name Reaction Index

Organic Chemistry Help!

Virtual Textbook of Organic Chemistry

 Online Biology and Chemistry Education Center