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Chemistry 3719 - Organic Chemistry I

• Professor Dr. Peter Norris• Office 6014 Ward Beecher• Telephone (330) 742-1553• Email pnorris@cc.ysu.edu • Website http://www.as.ysu.edu/~pnorris/

public_html

• Recitation TA Jason McCartney• Lab TA’s Dan Berndt, Andy Fluxe, Hud

Risley, Rob Wardle

Chemistry 3719 – Organic Chemistry I

MWF 11.00-11.50 Cushwa B024

Professor: Dr. Peter NorrisOffice: 6014 Ward BeecherTelephone: (330) 742-1553Email: pnorris@cc.ysu.edu

Website: http://www.as.ysu.edu/~pnorris/public_htmlMessage Board: http://members2.boardhost.com/antiperiplanar/

Textbook: “Organic Chemistry” 4th Ed. By F.A. Carey

The accompanying study guide is highly recommended, as are a set of molecular models.

GeneralOrganic chemistry is essentially the study of the compounds formed by carbon, of which over 6

million have been identified to date. The subject is the basis for biochemistry and genetics, and is thebackbone of industries such as pharmaceuticals, oil, dyes and cosmetics. Whether you intend to studychemistry, biology, pharmacy, medicine or engineering, an understanding of the fundamentals of organicchemistry is essential.

In two semesters we can only hope to cover the basics, however this still amounts to a very largeamount of material. It is very easy to get swamped in this class by not studying from the beginning in aconsistent manner. Since organic chemistry builds on general chemistry you have to be comfortable withthe material you learned in the 515-517 sequence, and be ready to use it from the first day in 3719. Sincewe will not have time in class to cover every detail in the text, it is essential that you get into the habit ofstudying your notes and the text at night, and then working the suggested problems to see if you understandthe material.

The lecture and laboratory portions of the organic chemistry are designed to coincide as much aspossible since everything discussed in lecture is the result of past experimental work. You will findyourself using the lecture text to work out problems from the lab, and hopefully this will help you see thatthe two are closely interconnected.

Course PhilosophyWith the change from quarters to semesters we have had the opportunity to rethink the organic

chemistry sequence and have therefore changed both lecture and lab texts. One of the problemsencountered in the past has been the lack of reactions early on in the sequence and then an overload ofreactions later in the year. This has been addressed with the introduction of the new text, which takes the“functional group” approach to organic chemistry in which classes of molecules, and their reactions, aredealt with in turn. This change of pace, along with the greater time for subject development allowed bysemesters, will hopefully aid your progress in the subject.

Additionally, a major stumbling block for many students is the inability to visualize molecules in 3-D,which is essential for the study of stereochemistry and its effects in structure and reactivity. The use of the“Learning with Molecular Modeling” CD that is included in the text is expected to help in this aspect of thecourse. The modeling package on CD is based on the Spartan program. We have the full version of thismodeling package on each of the PC’s found in the two computer labs on the 5

th floor of Ward Beecher.

Between the professor, the lab TA’s and the material available on the Web, we will attempt to assistyou as much as possible during 3719 so that you can get to grips with a difficult but incredibly fascinatingand important subject.

GradingThere will be three 50 minute term exams (see attached schedule for dates) worth 100 points each and

a 200 point comprehensive final. Chemistry 3719L is worth 100 points for a total of 600 points for3719/3719L.

The following grading scale will be used with adjustments made as needed depending upon overallclass performance:

Chemistry 3719 – Organic Chemistry I Fall Semester 2000

Lecture Schedule

Week Chapter and Topic Assigned Problems

1IntroductionChapter 1 – Chemical bonding, electronegativity,hybridization, resonance

1.1-1.24, 1.26, 1.28, 1.30, 1.31, 1.34, 1.36, 1.43, 1.46

2Chapter 2 – Alkanes, classification, functionalgroups, nomenclature, natural occurrence, physicaland chemical properties

2.1-2.22, 2.24-2.31, 2.34-2.40, 2.43-2.45

3Chapter 3 – Conformational analysis on alkanes,structures of cycloalkanes, conformational analysison cyclohexanes

3.1-3.14, 3.16-3.26, 3.29, 3.31, 3.33, 3.37-3.40

4Chapter 4 – Alcohols and alkyl halides, naming,properties, acids/bases, alkyl halides from alcoholsExam 1 – 100 points – 9/22/2000

4.1-4.24, 4.27-4.32, 4.34-4.36, 4.39-4.40, 4.42, 4.44

5Chapter 4 – Mechanism of alkyl halide formation,carbocations, radical halogenation, halogenation ofhigher alkanes

6Chapter 5 – Alkenes and elimination reactions,naming alkenes, relative stabilities, mechanism offormation (E1 vs E2)

5.1-5.21, 5.23, 5.26, 5.28-5.33, 5.36-5.47

7Chapter 6 – Addition reactions of alkenes, regio-chemistry, electrophilic and free radical additions,use of different reagents

6.1-6.24, 6.28-6.32, 6.35-6.38, 6.45-6.54

8Chapter 6 – Completion of addition reactionsChapter 7 – Stereochemistry, chirality, namingsystem, multiple stereocenters

7.1-7.34, 7.36, 7.40, 7.43, 7.45, 7.47-7.48

9Chapter 7 – Resolution of enantiomers,stereochemistry in polymersExam 2 – 100 points – 10/27/2000

10Chapter 8 – Nucleophilic substitution, SN2 vs SN1,stereochemical features, solvent effects, leavinggroup and nucleophile abilities

8.1-8.24, 8.26-8.34, 8.37-8.43, 8.45-8.47

11Chapter 9 – Alkynes, preparation, acidityChapter 10 – Conjugated systems, additions todienes, the Diels-Alder reaction

9.1-9.10, 9.14-9.15, 9.17-9.21, 9.28, 9.3110.1-10.27, 10.29-10.30, 10.35-10.38, 10.40

12Chapter 11 – Arenes and aromaticity, structure ofbenzene, reactions at benzylic carbon, Huckel’srule and heterocyclic aromatic systems

11.1-11.21, 11.23-11.30, 11.32-11.34, 11.37-11.40,11.46

13Chapter 12 – Electrophilic aromatic substitution,mechanism, types of reagents, rates of reactionExam 3 – 100 points – 11/24/2000

12.1-12.36, 12.40-12.44

14Chapter 12 – Second substitution on benzene,regioselectivity, multiple substituentsChapter 13 – Spectroscopy, introduction to NMR

13.1-13.11

15Chapter 13 – Shielding and chemical shift, splittingpatterns Chapter 13 will be continued in Chemistry 3720

Final Exam – 200 points (cumulative)

Web Resources

“Owww, they have the Internet on computers now…..”

H. Simpson

http://www.as.ysu.edu/~chemistry

http://www.as.ysu.edu/~pnorris/public_html

Chemistry Computer Lab

North end of Ward Beecher on the 5th floor

24 233 MHz Pentium machines (Gateway)

2 Hewlett Packard network laserjet printers

1 Student assistant

All PC’s have MS Office, ChemDraw, ChemSketch, ACD NMR prediction software, Spartan molecular modeling package, Netscape Navigator and MS Internet Explorer

Open 9-5 Mon through Fri (see lab door for schedule)

What is Organic Chemistry?

The study of the compounds that contain carbon and the reactions of those materials (over 6 million known)

Why a whole year of Organic?

Carbon can bond in multiple ways to form a huge number of different molecules, and these compounds form the basis of many different disciplines, e.g.:

Biology (DNA, proteins, carbohydrates)

Medicine and Pharmaceuticals (Aspirin, Taxol, AZT)

Chemical Engineering (oil, plastics, fine chemicals)

2

Timeline

1807 Berzelius introduces the term “Organic Chemistry” to describe

the study of compounds isolated from nature

1828 Wohler makes urea, the first natural organic compound to be

synthesized in the laboratory

1890 Fischer studies the chemistry of proteins, carbohydrates and

the nucleic acids

1950 Woodward and Eschenmoser complete the first total synthesis

of Vitamin B12

1990 Kishi, Nicolau, Smith, Schreiber, etc. complete total syntheses

of compounds such as Brevetoxin B, Taxol, etc.

H2N

O

NH2

UREA - 1828

Palytoxin

Brevetoxin B

Organic Synthesis

Taxol - 1996 Nicolau and Holton total syntheses ~60 synthetic steps in each

Starting material (cheap) Products (expensive)

Chemistry 3719 and 3720 (and labs)

Lectures

• Structure and nomenclature of compounds and groups

• Physical properties and analysis of materials

• Reactivity and transformations with reagents

• Importance of organic compounds in society

Labs

• Glassware and equipment used to prepare organics

• Instrumentation used to analyze compounds

• Writing detailed reports of lab preparations

Organic Chemistry at YSU

• B.S. and M.S. degrees in Chemistry

• State of the art instrumentation (>$1,000,000 worth)

• Active research programs (Norris and Jackson)

• Student involvement in 3719/20, 4850, 6990

• Students present at regional and national meetings

• Undergrad and graduate students publish in journals

• Companies come to recruit our students

• Students move on to top graduate programs (Penn,

Wisconsin, Ohio State, Purdue