Laboratory Information

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



10/11 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


10/25 No Lecture-Lab Midterm


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


are needed to see this picture.O CH3

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



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



So can organic molecules only be good?



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.



Dendrobates histrionicus lives in rainforest of Colombia and Ecuador.

HN

N Cl



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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