Click here for C. J. Rizzo's Chem 220b and Chem 220c pages.
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Questions & Answers Page: I am posting questions and answers from the class, sent to me via email.
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):
Lab Text (required): The Organic Chem Lab Survival Manual,
J. W. Zubrick
Class pak (Campus Copy)
Laboratory Notebook (Hayden-McNeil)
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:
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.
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:
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.
"I pledge my honor that I have neither given nor received aid on this examination"
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.
|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)|
|Fri||Sept 6||Chapter 3: Organic Compounds: Alkanes and Cycloalkanes||Chapter 3 Slides (updated)|
|Mon||Sept 9||Chapter 3 (con't)|
|Wed||Sept 11||Chapter 3 (con't)|
Chapter 4: Stereochemistry of Alkanes and
|Chapter 4 slides (revised)|
|Mon||Sept 16||Chapter 4 (con't)|
|Wed||Sept 18||Chapter 4 (con't)||
Chair-Chair Interconversion of cyclohexane (animated gif)
|Fri||Sept 20||EXAM 1: CHAPTERS 1-4|
|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)|
|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)||
|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
|Fri||Oct 18||Chapter 8 (con't)|
|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)|
|Wed||Oct 30||Chapter 10: Alkyl Halides (answers)||Chapter 10 Slides|
|Fri||Nov 1||Chapter 10 (con't), QUIZ 2|
|Mon||Nov 4||Chapter 10 (con't)|
|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|
|Mon||Nov 18||Chapter 12 (con't)||Table of Exact Masses|
|Wed||Nov 20||Chapter 12 (con't)||
(courtesy of Dr. Ian Hunt, Univ of Calgary)
|Fri||Nov 22||Chapter 13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy||Chapter 13 slides (updated)|
||Fall Break (no classes)|
|Mon||Dec 2||Chapter 13 (con't)||
(you need the Shockwave plug-in to view these)
|Wed||Dec 4||Chapter 13 (con't)|
|Fri||Dec 6||Chapter 14: Conjugate Dienes and Ultraviolet Spectroscopy||Chapter 14 Slides|
|Mon||Dec 9||Chapter 14 (con't)|
|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
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