ORGANIC CHEMISTRY 1 CHEM A FALL 2004 SYLLABUS

Transcription

1 ORGANIC CHEMISTRY 1 CHEM A FALL 2004 SYLLABUS DR. D. ANDREW KNIGHT Office: Monroe 231 Phone: daknight@loyno.edu Web:

2 INTRODUCTION AND OBJECTIVES Organic Chemistry 1 (A ) is an introductory course in organic chemistry covering ten main subject areas: 1. Principles of bonding (Ch 1) 2. Introduction to organic compounds: functional groups, nomenclature, physical properties of simple organic compounds, conformations of alkanes, conformations of cyclohexanes and fused rings. (Ch 2) 3. Alkenes: structure, nomenclature, reactivity, thermodynamics and kinetics (Ch 3) 4. Reaction of alkenes: addition of hydrogen halides; carbocations; transition states; electrophilic addition of water/alcohols/halogens; oxy- and alkoxymercuration; addition of borane, radicals and hydrogen, reactions and synthesis. (Ch 4) 5. Stereochemistry: isomers; chirality; drawing and naming enantiomers; optical activity, optical purity, determination of % ee; polarimetry, CIP system; reactions of compounds with an asymmetric carbon; enantiotopicity, diastereotopic hydrogens and prochiral carbons; nitrogen and phosphorus chirality centers; stereochemistry of addition to alkenes, and enzyme catalyzed reactions. (Ch 5) 6. Alkynes: nomenclature; physical properties; reactivity: addition of water/hx/halogens/hydrogen/borane; synthesis using acetylide anions; commercial uses of ethyne. (Ch 6.) 7. Electron delocalization and resonance; electronic effects, structure and bonding in benzene; resonance structures; resonance contribution; resonance energy; allylic/benzylic cations and radicals; pka; MO theory and stability. (Ch 7) 8. Spectroscopy of organic compounds: uv-vis, mass spectroscopy, IR, NMR. (Ch. 8, Ch. 13, Ch. 14) 9. Reactions of alkanes. Radical chemistry. (Ch 9). 10. Reactivity at sp 3 carbons (Ch 9, Ch10). In addition to extending and reinforcing the basic knowledge of topics such as structure and bonding that were introduced in General Chemistry, important new areas such as organic functional groups, stereochemistry and spectroscopy will be introduced. The aims of the course are to increase familiarity with the basic fundamentals of organic chemistry, and to recognize the impact of organic chemistry on our daily lives. Lectures will be held in Monroe 157 and will begin promptly at 11:30 am on Monday, Wednesday and Friday, and will run until 12:20 am. Attendance at lectures is expected. Tutorials may be scheduled periodically throughout the course, WEB SITE AND LISTSERVE CHEM A will make use of blackboard, and some lecture notes will be made available as pdf or ppt files. Students should develop a habit of routinely checking the A blackboard site located at: COURSE TEXT BOOK: Organic Chemistry, Bruice, P. Y. 4th edition. Prentice Hall, The text book provides a good guide to most of the topics which will be covered in Organic Chemistry 1. In addition, a solution guide and study manual by the same author is available. Students are also encouraged to acquire a good set of molecular models.

3 For supplementary, detailed description of some of the topics in the course, students should consult the references listed below. ADDITIONAL REFERENCES W. H. Brown and C. S. Foote, Organic Chemistry, 3 rd edition, Brooks/Cole, (2002). F. A. Carey, Organic Chemistry, 5 th edition, McGraw Hill (2000). F. A. Carroll, Perspectives on Structure and Mechanism in Organic Chemistry, Brooks/Cole Publishing Co. (l998). S. N. Ege, Organic Chemistry, 4 th edition, D.C. Health and Company, Lexington (1999). W. C. Groutas, Organic Reaction Mechanisms, John Wiley and Sons, Inc. New York (2000). M. Jones, Organic Chemistry, 2nd edition, W. Norton & Company, Inc. (2000). G. Mare London, Organic Chemistry, 4 th edition, Oxford University Press, New York (2002). J. McMurray, Organic Chemistry, 6 th edition, Brooks/Cole Publishing Company, Monterey (2004). A. Miller and P. Solomon, Writing Reaction Mechanisms in Organic Chemistry, 2nd edition, Academic Press (2000). S. Rosenfeld, Basic Skills for Organic Chemistry, Jones and Bartlett Publishers, Boston (2000). P. H. Scudder, Electron Flow in Organic Chemistry, West Publishing Co. (1992). G. Solomons and C. Fryhle, Organic Chemistry, 7 th edition upgrade, John Wiley &Sons, Inc., New York, (2002) P. Svoronos and Ed Sarlo, Problems Workbook for Organic Chemistry, Wm. C. Brown Publishers (1993). L. G. Wade, Organic Chemistry, 5 th Edition, Prentice Hall (2003). D. P. Weeks, Publishing Electrons. A guide for students of Organic Chemistry, 2nd edition, Saunders College Publishing (1995). REFERENCES FOR PLANNING A LOGICAL CHEMICAL SYNTHESIS M.B. Smith, Organic Synthesis, McGraw Hill, Inc, (1994). R.O.C. Norman and J.M. Coxon, Principles of Organic Synthesis, 3rd Ed., Blackie Academic and Professional (1993 HOMEWORK Homework may be assigned during the course. Students are encouraged to prepare for the examinations by completing the relevant problems at the end of each Chapter.

4 METHOD OF ASESSMENT AND GRADING: Your final grade will be determined on the basis of four components, which will be distributed as follows: Three 50 min in-class exams will be given and a comprehensive, two-hour final exam. The anticipated dates of the in-class examinations are listed below and may be subject to change. No make-up or early exams will be given unless under exceptional circumstances. Calculators may not be used during the examinations. Please note that, using a total point scheme to determine final grades, "letter grades" cannot be given to any individual exam performance. However you can monitor your progress by the relationship of your score to the class average. The final exam score and the average score from all four exams combined will be compared to decide the final grade (i.e. the higher of the two possible grades is used). DATE EXAMINATION TIME POINTS September 22 (W) 1 50 min 100 October 22 (F) 2 50 min 100 November 15 (M) 3 50 min 100 December 15 (W) am FINAL 2 hrs 200 An overall mark of 55% is normally considered adequate passing standard and it is not necessary to achieve a pass in every component of Organic Chemistry 1. Marks may be subject to scaling before final grades are awarded. ANTICIPATED GRADING SCALE A B B C C D D <55 FAIL REVIEW SESSION (TENTATIVE) AND MOCK EXAMS A review session may be given before the final exam and the date will be announced sometime during the semester. Please note that mock-exams and previous tests are not currently available for Organic Chemistry 1 although some selected questions from previous tests will be made available on Blackboard. These questions should be consulted primarily as a guide to exam style and are not exhaustive compilations of complete exams. Representative exam-type questions will be presented during the lectures. ABSENCES No student will be excused from taking an exam at the scheduled time without the prior permission of the instructor. If you believe that you have a valid reason for requesting an excused absence, contact me before the exam either in person, or by phone. A grade of zero will be given for an absence. NOTIFIED CHANGES TO THE SYLLABUS The material in this syllabus outline is currently accurate, but deviations may be necessary as the semester progresses. Students must be sure that they are aware of such variations that may be announced on the listserve, in lectures, or on the CHEM A blackboard site. Please read and make sure that you understand the section on academic dishonesty, integrity of scholarship and grades, in the Loyola University Undergraduate Bulletin

5 CONSULTATION AND OFFICE HOURS Students are welcome and encouraged to consult the instructor on any aspect of the subject that is causing concern. In particular, if a section of work in the subject is causing difficulty, you should obtain help with this work as soon as possible. Office Hours: Monday, Wednesday, pm or by appointment