Chem 220a
Chem 220A: Section 1 Organic Chemistry Lecture (Fall 2009) T, R: 9:35 – 11:00 AM SC 4309 |
Carmelo J. Rizzo office: SC 7662 Tel.: 322-6100 e-mail: c.j.rizzo@vanderbilt.edu |
The Final Exam will be held on Wednesday, December 16 from 9:00 – 11:00 am in room SC 4309.
No alternative final exam date will be offered.
Office hours for Monday and Tuesday (Dec. 14 & 15): 11:00 – 12:00 and 1:00 – 2:00
Final exam review will be Monday, Dec. 14 at 5:30 -6:30 pm in SC 4327
You may use a calculator and molecular models on the final exam
Click here for C. J. Rizzo’s Chem 220b page.
You will need Adobe Acobat Reader to view pdf files.
updated: 12/.4/2009
Questions & Answers Page:
I am posting questions and answers from the class, sent to me
Required text: Organic Chemistry, 7th edition, Francis A. Carey
Student Solutions Manual to accompany Organic Chemistry, 7th Ed., Robert C. Atkins & Francis A. Carey (optional)
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.) $30.00
Office Hours: M, W: 10:00-11:00 am; T, R: 1:00 pm -2:00
pm and by appointment. Office hours are subject to change or
cancellation without prior announcement.
Drop-in hours with Dr. James Lowe (SC 7921, jim.lowe@vanderbilt.edu): M, W: 9:15-11:30 am ; T, R: 1:30 pm -4:30
pm
Course Content: Chapters 1-12, 14, 15.1-15.13 of Carey, see tentative class schedule below.
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 Wed. Dec. 16, 2009 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.
“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 at least 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: A Molecular Approach”, Nivaldo J. Tro
Pearson Prentice Hall Publishing: 2008
Electronic Structure: Chapter 8
Lewis Structure and Chemical Bonds: Chapter 9
VSEPR and Molecular Orbitals: Chapter 10
Atomic Orbitals: Chapter 7
Chemical Equilibrium: Chapter 14
Acid-Base Equilibrium: Chapters 15 and 16
Thermochemistry: Chapters 6 and 17
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: ΔG°= ΔH° – TΔS°
ΔG°= -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 Tables 3-3 and 3-5, pg. 94-95 of Tro) and the names and structures of common mineral acids (see Table 15.1, pg. 664 of Tro) and bases (see Table 15.2, pg. 666 of Tro)
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Tentative class schedule |
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Thur., Aug. 27 | Chapter 1: Structure Determines Properties | Slides for Chapter 1: pdf ; ppt
Problems: 1-18, 20-27, 29, 31, 32, 36, 38-44, 46-50, 52-54, 58, 61-64, 68, 69, 71 |
Tue., Sept. 1 | Chapter 2: Alkanes and Cycloalkanes: Introduction to Hydrocarbons | Slides for Chapter 2: pdf ; ppt
Problems: 1, 2, 4, 5, 7-11, 13, 14, 17-23, 25-29, 42, 43, 45 Orbital hybridization animation (courtesy of Dr. Ian Hunt, Univ of Calgary) |
Thur., Sept. 3 | Chapter 3: Alkanes and Cycloalkanes: Conformations and cis-trans Stereoisomers | Slides for Chapter 3: pdf ; ppt
Problems: 1-10, 12, 15, 17-22, 24-26, 29, 30, 36, 39 |
Tue., Sept. 8 | Chapter 3: (con’t) | Newman projections of ethane, propane and butane (animated gifs)
Energetics of the rotation of ethane, rotation of butane, and a chair-chair interconversion |
Thur., Sept. 10 | Chapter 4: Alcohols and Alkyl Halides | Slides for Chapter 4: pdf ; ppt
Problems: 1-18, 20-22, 25, 28, 34-43, 48, 50, 52, 53 |
Tue., Sept. 15 | Chapter 4: (con’t) | |
Thur., Sept. 17 | Exam 1, Chapters 1-4 | Exam 1 / answers |
Tue., Sept. 22 | Chapter 5: Structure and Preparation of Alkenes: Elimination Reactions | Slides for Chapter 5 (revised 9/23/09): pdf ; ppt
Problems: 1-5, 7-12, 14-22, 24-27, 29-31, 33-40, 42, 45-49 |
Thur., Sept. 24 | Chapter 5: (con’t) | |
Tue., Sept. 29 | Chapter 6: Addition Reactions of Alkenes | Slides for Chapter 6 (updated 9/27/09): pdf ; ppt
Problems: 1-8, 11, 12, 16, 18-20, 22-24, 26-29, 31, 32, 34, 36-39, 41, 43, 47, 57-60, 62 |
Thur., Oct. 1 | Chapter 6: (con’t) | Reactions of alkenes summary |
Tue., Oct. 6 | Chapter 7: Stereochemistry | Slides for Chapter 7 (updated 10/02/09): pdf ; ppt
Problems: 1-15, 17, 18, 20, 21, 23, 26, 28-31, 33, 35-38, 40, 42 |
Thur., Oct. 8 | Chapter 7: (con’t) | |
Tue., Oct. 13 | Chapter 8: Nucleophilic Substitution | Slides for Chapter 8 (revised 10/15/09): pdf ; ppt
Problems: 1-13, 15-19, 21, 25, 29-34, 37, 38 |
Thur., Oct. 15 | Chapter 8: (con’t) | (mid-semester deficiency report due) |
Tue., Oct. 20 | Exam 2, Chapters 1-8 | Exam 2 / answers |
Oct. 22-23 | October Break- no class | |
Tue., Oct. 27 | Chapter 9: Alkynes | Slides for Chapter 9: pdf ; ppt
Problems: 2, 4-18, 20-29, 31-34 |
Thur., Oct. 29 | Chapter 10: Conjugatation in Alkadienes and Allylic Systems | Slides for Chapter 10 (updated 10/28/09): pdf ; ppt
Problems: 1, 3-19, 21-23, 26-31, 33-35, 39, 40 |
Tue., Nov. 3 | Chapter 10: (con’t) | |
Thur., Nov. 5 | Chapter 11: Arenes and Aromaticity | Slides for Chapter 11 (updated 11/4/09): pdf ; ppt
Problems: 1-14, 16, 18, 19, 21-24, 27-31, 33-38, 40-44, 48, 50, 52 |
Tue., Nov. 10 | Chapter 11: (con’t) | |
Thur., Nov 12 | Chapter 12: Reactions of Arenes: Electrophilic Aromatic Substitution | Slides for Chapter 12 (revised 11/12/09): pdf ; ppt
Problems: 1-8, 10, 12-21, 24-36, 39 |
Tue., Nov. 17 | Chapter 12: (con’t) | Summary of electrophilic aromatic substitution |
Thur., Nov. 19 | Exam 3, Chapters 1-12 | Exam 3 / answers |
Nov 21-Nov 29 | Thanksgiving Break – no classes | |
Tue., Dec. 1 | Chapter 14.1-14.13: Organometallic Compounds | Slides for Chapter 14: pdf ; ppt
Problems: 1-12, 17, 19, 21-30, 32, 37 |
Thur., Dec. 3 | Chapter 14.1-14.13: (con’t) | Reactions of alkenes summary (updated) |
Tue., Dec. 8 | Chapter 15.1-15.13: Alcohols, Diols, and Thiols | Slides for Chapter 15: pdf ; ppt
Problems: 1-6, 8-10, 12, 14-16, 18-30, 32-38, 41 |
Thur., Dec. 10 | Chapter 15.1-15.13: (con’t) | organic synthesis problems (answers) |
Wed. Dec. 16, 9:00 – 11:00 am | Final Exam, SC 4309, Chapter 1-12, 14.1-14.13, 15.1-15.13 | |
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: 1-18, 20-27, 29, 31, 32, 36, 38-44, 46-50, 52-54, 58, 61-64, 68, 69, 71
Chapter 2 Problems: 1, 2, 4, 5, 7-11, 13, 14, 17-23, 25-29, 42, 43, 45
Chapter 3 Problems: 1-10, 12, 15, 17-22, 24-26, 29, 30, 36, 39
Chapter 4 Problems: 1-18, 20-22, 25, 28, 34-43, 48, 50, 52, 53
Chapter 5 Problems: 1-5, 7-12, 14-22, 24-27, 29-31, 33-40, 42, 45-49
Chapter 6 Problems: 1-8, 11, 12, 16, 18-20, 22-24, 26-29, 31, 32, 34, 36-39, 41, 43, 47, 57-60, 62
Chapter 7 Problems: 1-15, 17, 18, 20, 21, 23, 26, 28-31, 33, 35-38, 40, 42
Chapter 8 Problems: 1-13, 15-19, 21, 25, 29-34, 37, 38
Chapter 9 Problems: 2, 4-18, 20-29, 31-34
Chapter 10 Problems: 1, 3-19, 21-23, 26-31, 33-35, 39, 40
Chapter 11 Problems: 1-14, 16, 18, 19, 21-24, 27-31, 33-38, 40-44, 48, 50, 52
Chapter 12 Problems: 1-8, 10, 12-21, 24-36, 39
Chapter 14 Problems: 1-12, 17, 19, 21-30, 32, 37
Chapter 15 Problems: 1-6, 8-10, 12, 14-16, 18-30, 32-38, 41
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)
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