Chemistry 110a - Organic Chemistry Course Syllabus
Pomona College
Fall Semester 2004
Lecture: MWF, 11:00 AM, Seaver North 111 Instructor: Prof. Carolyn Anderson, 607-8974 Seaver North 118 Email: [email protected] Office hours: MWF: 1-2 PM Dept. Secretary: Wanda Peters, 621-8410
Required Course Material Solomons and Fryhle, "Organic Chemistry", John Wiley & Sons, 8th Ed., 2003. Solomons, Fryhle, and Johnson, "Study Guide and Solutions Manual to Accompany Organic Chemistry, 8th Ed.", John Wiley & Sons, 2003. Darling Molecular Model Kit
110a Material Available Online
http://pages.pomona.edu/~cea04747/chem110a/index.html
Course Objectives You will be expected to become familiar with, and conversant in, fundamental aspects of organic chemistry.
Course Requirements
Five 100 pt 50-minute lecture examinations will be given as follows: 1. September 17 2. October 1 3. October 15 4. November 5
5. November 19 Introductory organic chemistry is a cumulative subject, and 110a exams will expect an integration of fundamental ideas as they are presente d. A cumulative final exam (3 hr, 200 pts) will be held on Monday, December 13th at 9:00 AM. The lowest non-final exam score will be dropped, and a percentage of 600 total points will determine the lecture letter grade, using a fixed scale. The lecture grade is then converted to the Pomona College scale (A=12, B=9, etc.) and combined in a weighted manner with the laboratory grade (similarly converted out of the total laboratory points) to assign a grade for the course. 75% of the course grade constitutes the lecture material, while 25% reflects laboratory proficiency.
Lecture Grading Scale
A 88+ C 52-57
A- 82-87 C- 46-51
B+ 76-81 D+ 40-45
B 70-75 D 34-39
B- 64-69 D- 28-33
C+ 58-63 F <27
110a Course Calendar- Fall 2004
Exam 1 Material
Date Topic Reading
9/1 Introduction: Lecture and Lab. -
9/3 Background/Bonding 1
9/6 Bonding 1
9/8 Representative Organic Compounds
2
9/10 Molecular Forces/IR 2
9/13 IR/Acid-Base Chemistry 2/3
9/15 Acid-Base Chemistry 3
9/17 Exam 1 1-3
Exam 2 Material
Date Topic Reading
9/20 Alkanes 4
9/22 Alkanes 4
9/24 Alkanes 4
9/27 Stereochemistry 5
9/29 Stereochemistry 5
10/1 Exam 2 4-5
Exam 3 Material
Date Topic Reading
10/4 Ionic Reactions 6
10/6 Ionic Reactions 6
10/8 Ionic Reactions 6
10/11 Alkenes and Alkynes I 7
10/13 Alkenes and Alkynes I 7
10/15 Exam 3 6-7
Exam 4 Material
Date Topic Reading
10/18 No Lecture-Fall Break
10/20 Alkenes and Alkynes II 8
10/22 Alkenes and Alkynes II 8
10/25 No Lecture-Lab Midterm
10/27 Alkenes and Alkynes II 8
10/29 NMR 9
10/31 NMR 9
11/03 NMR & Mass Spectrometry 9
11/05 Exam 4 8-9
Exam 5 Material
Date Topic Reading
11/08 Radicals 10
11/10 Radicals 10
11/12 Alcohols I 11
11/14 Alcohols I 11
11/17 Alcohols I 11
11/19 Exam 5 10-11
Material to be Included on the Final Exam
Date Topic Reading
11/22 Alcohols II 12
11/24 Special Topic – TBA handout
11/26 No Lecture-Thanksgiving Recess -
11/29 Alcohols II 12
12/1 Alcohols II 12
12/3 No Lecture-Laboratory Final -
12/6 Conjugated Unsaturated Compounds
13
12/8 Conjugated Unsaturated Compounds
13
12/13 Final Exam, 9:00 AM 1-13
Important Policies and Procedures- Chemistry 110a
1. Review Sessions will be scheduled prior to each exam. Dates and times will be announced in class. 2. Exam Grading. Look over your exam carefully. If you have any
questions concerning the grading, see me within 7 days following the exam.
3. Test Answers. Once the exams have been graded, the exam key
will be posted in Seaver North and on the course web page. 4. Make-up Exams will be arranged only in the case of verifiable extenuating circumstances. 5. Tutors are available through the office of the Dean of Students. 6. Students should feel welcome to telephone, email, or visit me for
assistance with course material. 7. The key to success in this course is to learn the basic material and to
apply it to solving problems. Read your lecture notes and the book and then try to solve the textbook problems on your own.
Laboratory Information
1) Laboratory sections will begin next Monday, September 6th
2) You should know which day (M, T, R, or F) you are registered for, if not, see: Professor Etzenhouser.
3) You should attend the laboratory section to which you are registered.
4) Lab manuals are available at the stockroom ($16) and should be purchased prior to the first day of lab.
5) Read the first lab before attending your laboratory next week.
Why Study Organic Chemistry?
a) I have to for my major.
b) O. Chem is on the MCAT.
c) I thought that I would punish myself.
d) O. Chem is actually interesting and directly affects the world we live in.
It is socially responsible to have an educated perspective regarding these issues ….and it can be FUN too!
How does Organic Chemistry Positively Affect the World?
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Natures Pharmaceuticals
MORPHINEIsolated from opium poppy,
Papaver Somniferous
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O
O OH
ASPIRINprecursor isolated from
willow bark
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Synthetic Pharmaceuticals
Lipitor (Atorvastatin Calcium) Pfizer
indicated for reduction of cholesterol levels
2003-world’s top selling drug–$8 billion/yr
O
O
N
CH3H3C
NH
O
OHOH
F
2
Ca+2
N
O
CH3
H3C
OH
HO
O
H3C
OHH3C
H3C
O
O
H3CCH3
OH
OCH3
H3C
O
CH3
N CH3
H3C
HOCH3
CH3
Zithromax (Azithromycin) Pfizer
antibiotic
2003-$2 billion/yr
What about Plastics?Polyethylene (PE) is the most common plastic in the US:
Low Density PE High Density PE grocery and garbage bags milk jugs, bulletproof vests (1999–9 billion lb/yr) (1999–8 billion lb/yr)
C C C C C C C
H
HH
H
H
H
H
H
H
H
H
H
H
H
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http://www.psrc.usm.edu/macrog/pp.htm
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Are there polymers other than plastics? Biomaterials
http://www.chem.uci.edu/people/faculty/zguan/
OO
OCH3
OCH3
OCH3
OCH3OCH3
OCH3
OCH3
OCH3O
O
polyester derived from a carbohydrate
Potential Uses:
drug deliverybiosensorstissue regeneration
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So can organic molecules only be good?
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Amphibian Poisons
http://www.asanltr.com/ASANews-99/995frogs.htm
Epipedobates tricolor, poison-dart frog from Ecuador, produces epibatidine a nicotine derivative with very strong analgesic activity. Epibatidine is 200 times more active than morphine. High toxicity hinders epibatidine from becoming a drug.
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Dendrobates histrionicus lives in rainforest of Colombia and Ecuador.
HN
N Cl
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epibatidine
Pollution
1995 Nobel Prize in chemistry was given for “their work in atmospheric chemistry, particularly concerning the formation and decomposition of ozone”--specifically the role that chlorofluorocarbons (CFC’s) play
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Paul J. Crutzen Mario J. MolinaF. Sherwood Rowland
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Common CFC’s
http://ausetute.com.au/cfcozone.html
refrigeration, aerosols, foams dry cleaning
K CCl3F (g) CCl2F (g) + Cl (g)
Cl (g) + O3 (g) ClO (g) + O2 (g)
O3 (g) O2 (g) + O (g)
ClO (g) + O (g) O2 (g) + Cl (g)
UV radiation
UV radiation
Cl
CF
ClCl
F
CF
ClCl
C C
F
FCl
Cl
FCl
Substitutes for CFC’s
refrigeration, foams aerosols
H
CF
ClF
C C
F
FCl
H
HH
Chemical Weapons
VX Gas:
Relatively non-volitile nerve agentLiquid when pure, becomes a gas upon expose to airHigh toxicity: ~10 mg exposure can kill the average personAs a weapon of mass destruction, delivery could be via aerosol or
water contamination
O
PO SH3C
H3CN
H3C CH3
CH3
CH3
http://www.why-war.com/encyclopedia/weapons/VXhttp://www.mayoclinic.com/
The antidote, Atropine, another small molecule
Serves to restore the normal balance of acetylcholine in the body and reverses the effects of nerve gas exposure
Small organic molecules, such as VX gas, pose global concerns if they are mishandled……remember “The Rock”?
NH3C
O
O
OH
Why study organic chemistry?
a) Knowledge of O. Chem can lead to improvements in the world and in our quality of life
D! Organic chemistry can open the world to you!
b) Knowing about the dangers of some organic molecules can help us to better understand the challenges that face the world
c) Frogs and flowers are fun to look at
d) All of the above!
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