Chemistry Organic Chemistry I

Transcription

1 Chemistry Organic Chemistry I Professor Dr. Peter Norris Office 6014 Ward Beecher Telephone (330) pnorris@cc.ysu.edu Website public_html Recitation TA Jason McCartney Lab TA s Dan Berndt, Andy Fluxe, Hud Risley, Rob Wardle

2 MWF Cushwa B024 Professor: Dr. Peter Norris Office: 6014 Ward Beecher Telephone: (330) Chemistry 3719 Organic Chemistry I Website: Message Board: Textbook: Organic Chemistry 4 th Ed. By F.A. Carey The accompanying study guide is highly recommended, as are a set of molecular models. General Organic 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 the backbone of industries such as pharmaceuticals, oil, dyes and cosmetics. Whether you intend to study chemistry, biology, pharmacy, medicine or engineering, an understanding of the fundamentals of organic chemistry is essential. In two semesters we can only hope to cover the basics, however this still amounts to a very large amount of material. It is very easy to get swamped in this class by not studying from the beginning in a consistent manner. Since organic chemistry builds on general chemistry you have to be comfortable with the material you learned in the sequence, and be ready to use it from the first day in Since we will not have time in class to cover every detail in the text, it is essential that you get into the habit of studying your notes and the text at night, and then working the suggested problems to see if you understand the material. The lecture and laboratory portions of the organic chemistry are designed to coincide as much as possible since everything discussed in lecture is the result of past experimental work. You will find yourself using the lecture text to work out problems from the lab, and hopefully this will help you see that the two are closely interconnected. Course Philosophy With 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 problems encountered in the past has been the lack of reactions early on in the sequence and then an overload of reactions 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, are dealt with in turn. This change of pace, along with the greater time for subject development allowed by semesters, 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 the course. The modeling package on CD is based on the Spartan program. We have the full version of this modeling 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 assist you as much as possible during 3719 so that you can get to grips with a difficult but incredibly fascinating and important subject. Chemistry 3719 Organic Chemistry I Fall Semester 2000 Lecture Schedule Week Chapter and Topic Assigned Problems Introduction Chapter 1 Chemical bonding, electronegativity, , 1.26, 1.28, 1.30, 1.31, 1.34, 1.36, 1.43, 1.46 hybridization, resonance Chapter 2 Alkanes, classification, functional groups, nomenclature, natural occurrence, physical , , , and chemical properties Chapter 3 Conformational analysis on alkanes, structures of cycloalkanes, conformational analysis , , 3.29, 3.31, 3.33, on cyclohexanes Chapter 4 Alcohols and alkyl halides, naming, properties, acids/bases, alkyl halides from alcohols , , , , 4.42, 4.44 Exam points 9/22/2000 Chapter 4 Mechanism of alkyl halide formation, carbocations, radical halogenation, halogenation of higher alkanes Chapter 5 Alkenes and elimination reactions, naming alkenes, relative stabilities, mechanism of , 5.23, 5.26, , formation (E1 vs E2) Chapter 6 Addition reactions of alkenes, regiochemistry, electrophilic and free radical additions, , , , use of different reagents Chapter 6 Completion of addition reactions Chapter 7 Stereochemistry, chirality, naming , 7.36, 7.40, 7.43, 7.45, system, multiple stereocenters Chapter 7 Resolution of enantiomers, stereochemistry in polymers Exam points 10/27/2000 Chapter 8 Nucleophilic substitution, S N2 vs S N1, stereochemical features, solvent effects, leaving , , , group and nucleophile abilities Chapter 9 Alkynes, preparation, acidity , , , 9.28, 9.31 Chapter 10 Conjugated systems, additions to , , , dienes, the Diels-Alder reaction Chapter 11 Arenes and aromaticity, structure of benzene, reactions at benzylic carbon, Huckel s , , , , rule and heterocyclic aromatic systems Chapter 12 Electrophilic aromatic substitution, mechanism, types of reagents, rates of reaction , Exam points 11/24/2000 Chapter 12 Second substitution on benzene, regioselectivity, multiple substituents Chapter 13 Spectroscopy, introduction to NMR Chapter 13 Shielding and chemical shift, splitting patterns Chapter 13 will be continued in Chemistry 3720 Final Exam 200 points (cumulative) Grading There 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 for 3719/3719L. The following grading scale will be used with adjustments made as needed depending upon overall class performance:

3 Web Resources Owww, they have the Internet on computers now.. H. Simpson

4 Chemistry Computer Lab North end of Ward Beecher on the 5th floor 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)

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6 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)

7 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 B Kishi, Nicolau, Smith, Schreiber, etc. complete total syntheses of compounds such as Brevetoxin B, Taxol, etc.

8 O H 2 N NH 2 UREA Palytoxin Brevetoxin B

9 Organic Synthesis Starting material (cheap) Products (expensive) Taxol Nicolau and Holton total syntheses ~60 synthetic steps in each

10 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

11 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