Download Course Syllabus - San Diego Mesa College

Course Syllabus – Organic Chemistry 231- Department of Chemistry – San Diego Mesa College – Dr. F Zand
San Diego Mesa College
Welcome to Organic Chemistry I - Chem 231
Fall - 2010
Chem 231: Organic Chemistry
Phone: 619-388-2784
Section: 67186
Instructor: Farshid Zand, PhD
Office: I-301 (I-300 bldg)
Email: [email protected]
Course Syllabus
Lecture: Time- T-Th 8:00-9:25 AM Room-I-117
Office Hours : T-Th 1:00-2:00 PM
Other times available by appointment. Additional office hours will be added near
examination days.
Website: http://classroom.sdmesa.edu/fzand
You can copy all the hand-outs, practice tests, and answer keys for the tests and many more.
Remember: “Learning is an option not an obligation” and do not be afraid or ashamed of your
mistakes “Mistakes are the beauty of the human being”
Textbook: Organic Chemistry 7th edition by John McMurray., Brooks/Cole Thomson
Learning Pub., 1999. Student Guide and Solution Manual by Susan McMurray.
The books can be purchased at the Mesa bookstore.
Course Description, Goals, and Objectives;
This is the first semester of one year course in Organic Chemistry. It is designed primarily for
science majors. Major themes include, but are not limited, to bonding and molecular structure,
nomenclature, reaction mechanisms, synthesis, and an introduction to conjugated and aromatic
carbon based compounds. An emphasis is placed on the reactions of aliphatic compounds such as
alkanes, cycloalkanes, alkenes, alkynes, and alkyl halides. The organic chemistry literature, and
spectral interpretation using techniques such as infrared (IR) and nuclear magnetic resonance (NMR)
spectroscopy, is introduced to support the above topics. Chemistry 231 is a 3-unit lecture course in
Organic Chemistry. It stresses aliphatic compounds and includes an introduction to aromatic
compounds. This course will discuss molecular structures and stereochemistry of organic
compounds, reactivity, reaction mechanisms, organic syntheses and special topics. The goal of this
class is to give you a thorough understanding of organic chemistry and will lay the foundation for
future studies in biology, biochemistry, and more advanced chemistry courses. Please read the most
recent Mesa Catalog for general information about the college and details regarding other course
goals, objectives, and contents.
Course Requirements;
The perquisite for Chemistry 231 is 1 year of General Chemistry. You will need to have a good
understanding of general chemistry to do well in this class (especially orbitals, electronic
configurations, binding theory, acidity and electronegativity).
Course Materials;
We will cover chapters 1-11 and 17 of the textbook. You are responsible for the material covered in
the chapters and the assigned problems. The purpose of the lecture is to clarify the more difficult
material in the book and not all topics can be covered in the lecture period. This will require you to
learn from the book through reading and self study.
Subject
Most people find organic chemistry to be very difficult. It is estimated that this class will require a
minimum of 15 hours of time outside of class each week. A lot of material needs to be covered and
trying to memorize all of it is unnecessary since the point of the course is to develop an
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Course Syllabus – Organic Chemistry 231- Department of Chemistry – San Diego Mesa College – Dr. F Zand
understanding of the subject. To understand organic chemistry, I suggest that you read each chapter
before class. Doing this will make the lectures easier to follow and will help to clarify concepts that
You may have found difficult in the reading. After the lecture read the chapter again and do the
problems. Some students also find it useful to rewrite their notes.
Homework;
Working problems is essential to understanding organic chemistry. For homework assignments for
each chapter see the attached page. Do and try to understand all of the problems. DO NOT DO THE
PROBLEMS WITH THE SOLUTION BOOK OPEN. This is the worst thing that you can do for
yourself. If you do the problems in this manner you will not gain an understanding of the material
and you will perform poorly on the exams. The exam problems will be modeled after the homework
problems (some being almost identical) and examples in lectures and will be designed to test your
understanding of the reading, homework, and lecture examples. You are expected to keep up with
the homework. Organic chemistry can not be learned the night before the exam.
Grading and Exams;
All exams will be a combination of multiple choice and short essay questions. There will be 3
quizzes, 3 mid-term exams, and a final. The final will cumulative covering all the topics addressed
by the course. The quizzes are worth 20 points each, and mid-term exams are worth 100 points each.
The final exam is worth 200 points. The final will be cumulative covering all the topics addressed by
the course.
Your grade will be assigned at the end of the semester and the chapters covered on each exam and
the evaluation criterion is shown below:
89% A
79% B
62% C
49% D
Below 48%
F
Exam Points and schedule
Midterm 1
Chapters 1-5
100 Points
Thursday Sep 23
Midterm 2
Chapters 6-8
100 Points
Thursday Oct 28
Midterm 3
Chapters 9-11
100 Points
Thursday Dec 02
Final Exam: Chapters 1-17,comprehensive 200 points, Room I-117,Th 05/20- 8:00 am-09:30am
Other Administrative Matters;
It is your responsibility to follow college policies regarding withdrawals, drops, and incompletes.
Important Dates
Last Day to Receive and ADD CODE
Sep 03
Last Day to Apply for REFUNDS
Sep 07
Last Day to Drop With No W
Sep 03
Last Day to Withdraw
Oct 29
All drops must be initiated by student. This can be done by filing a drop form with the admissions
office before the withdrawal deadline Oct 29th . If you intend to drop the class, please file the
necessary paperwork, do not assume that I will drop you if you simply stop attending class; It is your
responsibility to drop the class if you decide to do so.
Students Rights and Responsibilities: District policy 3100 lists your rights and responsibilities as a
student. Act in accordance with this policy to make progress towards your educational goals. It is
your responsibility to read the assigned materials, read and follow the syllabus, course policy etc. It
is also your right to have a learning environment free of disruptions. Therefore horseplay and
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Course Syllabus – Organic Chemistry 231- Department of Chemistry – San Diego Mesa College – Dr. F Zand
Disruptive behavior in the class is unacceptable. In accordance to this policy you do not have the
right to take anyone else’s’ work or property (ie- cheating, plagiarism or stealing), harass or threaten
others at any time. Plagiarized work will not be graded and you will receive a zero on that
assignment. Any violation of the code of conduct may result in disciplinary sanctions.
Chapter Assignments
WEEK
DAY
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
Tues
Thurs
08-24 — 08-26
08-31 — 09-02
09-07 — 09-09
09-14 — 09-16
09-21 — 09-23
09-28 — 09-30
10-05 — 10-07
10-12 — 10-14
10-19 — 10-21
10-26 — 10-28
11- 02 —11- 04
11-09 —11- 11
11-16 — 11-18
11-30 — 12-02
12-07 — 12-09
12-14 — 12-16
CHAPTERS
COVERED
1&2
2&3
3&4
4&5
4&5
6&7
6&7
7&8
7&8
9 & 10
9 & 10
11
11
11 &17
17
17 & Review
EXAMS/QUIZZES
Quiz-1 (Tues)
Mid-term-1 (Thurs) Chaps 1-5
Quiz-2 (Tues)
Mid-term-2 (Thurs) Chaps 6-8
Quiz-3
Mid-term-3 (Thurs) Chaps 9-11
FINAL EXAM -Th 12 - 16
Final Exam: Chapters 1-17, Comprehensive 200 points, Room I-117, Thursday Dec 16 - 8:00 am - 09:30 am
ANY STUDENT NEEDING ACADEMIC ACCOMODATIONS SHOULD SEE ME THE
FIRST 2 CLASS PERIODS SO THAT WE CAN MAKE ARRANGEMENTS TO MAKE
THE CLASS MORE COMFORTABLE FOR YOU.
=======================================================================
Homework Problems
CHAPTER
1
2
3
4
5
6
7
8
9
10
11
17
HOMEWORK PROBLEMS
21-25, 26 (a-g), 28, 29, 31, 34-46
28, 29, 31, 33-37, 39, 40, 42, 44, 47-58
24, 25, 27-30, 32, 34, 38-39, 41, 43-45, 48-57
24, 25, 27, 29, 30, 32-36, 38, 39, 42-44, 46-50, 52-57
23-26, 28-30, 32-35, 38-44, 47-50
23-33, 35-44, 46-52
23, 24, 26, 29, 30, 31, 34, 35, 37, 38, 40, 42, 44, 45, 47-49, 51-53
19, 20, 22, 23, 25-27, 29, 31-34, 36-38, 40, 42
32-43, 44-56, 58-64, 70-82
17, 18, 20-22, 24-26, 28-30, 32, 34-42
25-30, 32-41, 43, 45-56, 58, 60, 62-68
26, 27, 29-34, 36, 37, 39-44, 48-54, 58-65
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Course Syllabus – Organic Chemistry 231- Department of Chemistry – San Diego Mesa College – Dr. F Zand
Chapter Contents
Chapter 1: Structure and Bonding
Atomic Structure-Orbitals- Electron Configuration- Development of Chemical Bonding Theory-The
Nature of Chemical Bonds- V-Bond Theory- Hybridization: sp3 (Ethane), sp2 (Ethylene), sp
(Acetylene)- Hybridization of Nitrogen and Oxygen, Molecular Orbital Theory
Chapter 2: Polar Covalent Bonds, Acids, and Bases
Electronegativity, Dipole Moments- Formal Charge- Resonance-Rules-Drawing Resonance FormsAcids & Bases- The Bronsted Lowry Definition- Strength- Predicting Acid-Base reaction from pKa
Values-Organic Acids & Bases, The Lewis Definition- Drawing Chemical Structures- Models
Chapter 3: Organic Compounds
Functional Groups- Alkane and Isomers- Naming- Properties of Alkanes- Cycloalkanes- Naming
Cycloalkanes- Cis-Trans Isomerism in Alkanes
Chapter 4: Stereochemistry of Alkanes and Cycloalkanes
Conformations of Ethane- Proapane-Butane-Stability of Cycloalkanes: The Baeyer Strain TheoryThe Nature of Ring Strain- Cyclopropane- Orbital View- Conformations of CyclobutaneCyclopentane and Cyclohexane-Axial and Equatorial Bonds of Cyclohexane- Conformational
Mobility of Cyclo hexane-Conformation of Monosubstituted and Analysis of Disubstituted
Cyclohexanes- Boat Cyclohexane
Chapter 5: Organic Reactions
How Organic Reactions Occur- Mechanisms-Radical Reactions-Polar Reactions-An Example of A
Polar Reaction: Addition of HBr to Ethylene-Using Curved Arrows in Polar Reaction MechanismsDescribing a Reaction: Equilibria, Rates, Energy Changes and Bond Dissociation EnergiesDescribing a reaction: Energy Diagrams-Transition States and Intermediates
Chapter 6: Alkanes: Structure and Reactivity
Preparation and Use of Alkenes-Calculating of Degree of Unsaturation-Naming Alkenes-Electronic
Structure of Alkenes- Cis-Trans Isomerism-The E-Z Designation-Stability of Alkenes- Electrophilic
Addition of HX to Alkenes-Orientation of Electrophilic Addition: Markovnikov’s RuleCarbocation-Structure and Stability- The Hammond Postulate-Evidence for the Mechanism of
Electrophilic Addition-Carbocation Rearrangements
Chapter 7: Alkenes
A Preview of Alimination Reactions- Addition of Halogens to Alkenes- Halohydrin FormationAddition of Water to Alkenes: Oxymercuration and Hydroboration- Addition of Carbenes to
Alkenes: Cyclopropane Synthesis. Reduction of Alkenes: Hydrogenation. Oxidation of Alkenes:
Hydroxylation and Cleavage. Biological Alkene Addition Reactions- Addition of Radicals to
Alkenes
Chapter 8: Alkynes
Electronic Structure of Alkynes-Naming Alkynes-Preparation of Alkynes: Elimination Reactions of
Dihalides-Reactions of Alkynes: Addition of HX and X2- Hydration-Reduction and Oxidative
Cleavage of Alkynes-Alkyne Acidity: Formation of Acetylide Anions-Alkylation of Acetylide
Anions
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Course Syllabus – Organic Chemistry 231- Department of Chemistry – San Diego Mesa College – Dr. F Zand
Chapter 9: Stereochemistry
Enantiomers and the Tetrahedral Carbon- The Reason for Handedness in Molecules: ChiralityOptical Activity-Enantiomers- Sequence Rules for Specification of Configuration-DiastereomersMeso Compounds-Molecules with More Than Two Chirality Centers-Physical Properties of
Stereoisomers-Racemic Mixtures and Their Resolution-Stereochemistry of Reactions: Addition of
HBr to Alkenes-Addition of Br2 to Alkenes-Addition of HBr to a Chiral Alkene-Chirality at Atoms
Other Than Carbon
Chapter 10: Alkyl Halides
Naming and Structure of Alkyl Halides-Preparing Alkyl Halides-Radical Halogenation of AlkanesAllylic Bromination of Alkenes-Stability of the Alkyl Radical: Resonance Revisited. Preparing
Alkyl Halides From Alcohols- Reaction of Organohalides: Grignard Reagents. Organometallic
Coupling Reactions
Chapter 11: Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
Stereochemistry of Nucleophilic Substitution- Kinetics of Nucleophilic Substitution-The SN2
Reaction-Characteristics of SN2 Reaction. The SN1 Reaction-Kinetics-Stereochemistry and
characteristics of the SN1 Reaction-Elimination Reactions of Alkyl Halides: Zaitsev’s Rule. The E2
Reaction. Elimination Reactions and Cyclohexane Conformation-The Deuterium Isotope Effect-The
E1 Reaction-Summary of Reactivity: SN1, SN2, E1, E2-Substitution Reactions in Synthesis
Chapter 17: Alcohols and Phenols
Naming Alcohols and Phenols-Properties of Alcohols and Phenols: H-Bonding-Acidity and
Basicity- Preparing Alcohol: A Review-Alcohols From Reduction of Carbonyl CompoundsAlcohols From Reaction of Carbonyls Compounds with Grignard Reagents-Some Reaction of
Alcohols- Oxidation of Alcohols- Protection of Alcohols- Preparation and Use of Phenols-Reactions
of Phenols-Spectroscopy of Alcohols and Phenols.
GOOD LUCK
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