Bucknell University

Chemistry 211 Organic Chemistry I

Fall 2000

Instructor: Professor John P. Scovill

VOICE: 270-577-3265

email: jscovill@bucknell.edu

Office Hours: MWF after class (10:00 — 11:30), other hours by arrangement

Lectures: Monday, Wednesday, and Friday at 9:00 —10:00 am

Recitation: Monday, 7:00 pm

Texts: Organic Chemistry, 5th Edition, John McMurry

Pushing Electrons, 2nd Edition, Daniel P. Weeks

Organic Chemistry Lab Survival Manual, James W. Zubrick

Molecular Structure Models, Organic Chemistry

Exam Schedule: Exam 1 (100 points) When: Lesson 14 Subject: Lessons 1-13

(Fridays) Exam 2 (100 points) When: Lesson 28 Subject: Lessons 15-27

Exam 3 ( 75 points) When: Lesson 37 Subject: Lessons 29-36

Quizzes: Quizzes (150 points) When: Wednesdays

Lab (100 points)

Final (125 points)

Total 650 points

Absences: Alternative arrangements can be made for absences due to athletic competition (provide schedule at beginning of the year or a note from the coach two weeks in advance of the event) or illness (with a note from the dean). Laboratory attendance is mandatory and missed labs ordinarily cannot be made up.

Academic habits: Organic chemistry is a vertical subject in which comprehension of the following lessons is highly dependent upon mastering each proceeding lesson. Lessons need to be prepared prior to the lecture. Don’t fall behind! Read the assignment and identify concepts which you find confusing. These should be brought up in class for clarification. The best route to success is daily preparation: a minimum of 2 _ hours of study for each hour in class usually affords the average student an average grade. The best way to study organic chemistry is to work organic chemistry problems. The more the better. Problems you attempted but could not complete should be brought up in class for discussion. For difficult problems, don’t turn to the solution manual or a classmate for help too soon. Frequently, this struggle is the most beneficial learning process for it is the route to in depth understanding and long term retention.

Honor policy: Read the sections dealing with academic impropriety in the University Bulletin. Material submitted for a grade is understood to be one’s own work. Suspected dishonesty will be referred to the Judicial Board for investigation.

Exam policy. Organic chemistry is a vertical subject and exams reflect the cumulative nature of the science. Exams will, however, emphasize material covered as described in the exam schedule.

Marking disputes: Please bring instructor math errors to my attention for immediate correction. If you believe that your mark on an exam is lower than you deserve, you may appeal your grade. Submit a brief, separate paper explaining what you what corrected and why your solution deserved a higher mark. Submit this to me along with the original exam within a week of the exam being returned to the class. The instructor reserves the right to regrade the entire exam and the new score (higher or lower) will be recorded. Only exams which have been written in permanent ink can be submitted for regrading.

Be sure to read the assignments before coming to class. Pay special attention to mastering the vocabulary of organic chemistry — learning a science is like learning a new language. Key concepts for each chapter are listed below. Be sure to work all of the problems. The ability to work the problems in the text book is your best indicator and predictor of success in this course.

Lsn Date Reading Assignment

1 30 Aug Chapter 1. McMurry

2 1 Sep Chapter 1. Weeks

3 4 Sep

Structure and Bonding. drawing Lewis structures, atomic structure, molecular orbitals, electronic configurations, ionic bonds, covalent bonds, valence bond theory and molecular orbital theory, coordination number, VSEPR theory, molecular geometry, hybridized orbitals of carbon (sp, sp2, and sp3), hybridized orbitals of boron, nitrogen and oxygen

4 6 Sep Chapter 2.

5 8 Sep Chapter 2. Weeks

6 11 Sep

Polar Bonds and Their Consequences. electronegativity, polar covalent bonds, bond polarity and molecular polarity - the dipole moment, the d+ and d- convention for polar bonds, electron deficient atoms, acidity, Bronsted - Lowry acids and bases, Lewis acids and bases, Lewis structures, resonance forms, curved arrows, molecular models

7 13 Sep Chapter 3.

8 15 Sep

9 18 Sep

10 20 Sep

Organic Compounds: Alkanes and Cycloalkanes. alkanes and cycloalkanes, functional groups, intermolecular forces of attraction, hydrogen bonding, physical properties, hydrophobicity, hydrophilicity, dipoles, polar molecules, solubility, cis-trans isomers

11 22 Sep Chapter 4.

12 25 Sep

13 27 Sep

14 29 Sep Exam 1

Stereochemistry of Alkanes and Cycloalkanes. conformation and stability, interconversions of conformational isomers, energy diagrams, Newman projections, thermodynamics and the composition of conformational isomers at equilibrium, ring strain

15 2 Oct Chapter 5.

16 4 Oct

17 6 Oct

18 11 Oct

An Overview of Organic Reactions. radical reactions, bond dissociation energies, polar reactions, mechanism, rates and equilibria, substitution reaction, addition reaction, energy diagrams, stereochemical consequences of mechanism, electrophiles and nucleophiles, Lewis acids and Lewis bases, electron deficient species, transition states, intermediates, Arrhenius equation

19 13 Oct Chapter 6.

20 16 Oct

21 18 Oct

22 20 Oct

Alkenes Structure and Reactivity. Degree of unsaturation, cis-trans isomerism in alkenes, the E-Z designation, electrophilic addition to alkenes, Markovnikov’s rule, carbocation stability and structure, carbocation rearrangements, Hammond postulate

Lsn Date Reading Assignment

23 23 Oct Chapter 7.

24 25 Oct

25 27 Oct

26 30 Oct

27 1 Nov

28 3 Nov Exam 2

Alkenes. Reactions and Synthesis. elimination reactions, addition of halogens to alkenes, fumarase, halohydrin formation, hydroboration, oxymercuration, addition of carbenes to alkenes, hydroxylation of alkenes, hydrogenation, cleavage of alkenes, radical additions to alkenes

29 6 Nov Chapter 8.

30 8 Nov

31 10 Nov

32 13 Nov

Alkynes. dehydrohalogenation of dihalides, addition of halogen to alkynes, addition of hydrogen halide to alkynes, hydration of alkynes, reduction of alkynes, acetylide anions and alkylation of alkynes

33 15 Nov Chapter 9.

34 17 Nov

35 20 Nov

36 27 Nov

37 29 Nov Exam 3

Stereochemistry. symmetry, symmetry operations, homomers, enantiomers, diastereomers, mirror plane, center of symmetry, assignment of absolute configuration (R and S system), chiral compounds, meso compounds, Fischer projection, racemates and resolution of racemates, stereochemistry and mechanism -- polar additions to alkenes

38 1 Dec Chapter 10.

39 4 Dec

40 6 Dec

41 8 Dec

42 11 Dec

Alkyl Halides. radical halogenation of alkanes, allylic bromination of alkenes, special stability of allyl radicals and allyl carbocations -- applications of resonance, alkyl halides from alcohols, Grignard reagents, organometallic coupling reactions