Lycoming Chemistry 440 Syllabus, Fall 1998

While every effort has been made to make sure this electronic syllabus is error-free, it is not official.
The definitive source of course information remains the original (paper) syllabus distributed in class.

Lycoming College Chem 440 Fall 1998 Advanced Organic Chemistry

Course description - This course is designed to further your understanding of modern organic chemistry. The laboratory component of the class is meant to introduce you (and me) to typical experiments within the discipline.

Instructor - Dr. Chriss McDonald, phone: 321-4186 (work), 433-4493 (home) [call up to 10pm], Email: mcdonald@lycoming.edu

Texts and other stuff
a.    Advanced Organic Chemistry, Part A, third edition by Carey and Sundberg (with readings from Part B
       as handouts)
b.    Bound laboratory notebook by Freeman
c.    Lab safety glasses
d.    Calculator (add, subtract, multiply, divide, logs, exponents)
e.    Chem 220-221 lab manual (your old one, whichever year it happens to be)

Other useful sources of information
a.    Your 200-level organic chemistry text (Schmid for most of you)
b.    Intermediate Organic Chemistry, by Stowell (in the reading room)
c.    Advanced Organic Chemistry, , by March (in the main library, and reading room)
d.    The chemical literature, specifically The Journal of the American Chemical Society [JACS],
       The Journal of Organic Chemistry [JOC], Tetrahedron Letters [TL] (in the main library except for               current issues which are in the reading room).

Course format

Lectures - MWF, 8:00 AM, HBC 215

Recitations - None scheduled, if you guys want some, let me know and we'll find a time to get together. We do have a few in class problem sessions scheduled. As always, questions are welcome at any time.

Assigned homework - problems designed to enhance your understanding and prepare you for testing situations. Some of these questions will be taken from the literature (which means you can go look up the answers!). Some homework assignments will have a student presentation format. A key will be posted immediately after class. No late homework will be accepted.

Laboratory - 8:00 - 11:50 AM, Thursday (some labs will be started during the lecture periods scheduled for earlier in the week)

Exams - Exams will occur during the lab period of the indicated week. They should be both fun and challenging.

Grading scheme
a. The final grade is based on the number of points obtained out of a possible 850 points. The points will be distributed as follows:

quizzes 60 points

exam 1 100 points

exam 2 100 points

exam 3 100 points

final exam (cumulative) 150 points

laboratory 200 points

student paper 60 points

homework 80points

total 850 points

b. Assignment of letter grades is based on the following scale: 850 -765 A, 764 - 680 B, 679 - 595 C, 594 - 510 D, < 510 F. I reserve the right to curve the grades if deemed appropriate based upon overall class performance and a qualitative assessment of the difficulty of quizzes and exams. Also, if you score a higher percentage on the final exam than one of your hour exams, I'll replace the lower score with the higher. The assignment of the final grade is also influenced by attendance and class participation. This is especially true in the case of a student with a borderline average.

c. BONUS POINTS! you will receive 3 bonus points for each chemistry department colloquium you attend.

Policy on attendance for exams and quizzes Makeups will be administered only if I deem the reason for absence to be legitimate (illness, death in the family....). Absence due to transportation difficulties is not considered legitimate.
SCHEDULE CHEM 440, 1998

date	topic	reading assignment	quiz/exam
8/31	This is Advanced Organic	A, the preface
9/2	polar reaction mechanisms	handout
9/4	enantiomerism	A 2.1
9/7	diastereomerism and resolution	A 2.2
9/9	dynamic stereochemistry	A 2.3
9/11	prochirality	A 2.4	QUIZ 1
9/14	acyclic conformational analysis	A 3.1,2
9/16	conf. analysis of carbocycles	A 3.3,4
9/18	conf. analysis of heterocycles	A 3.5
9/21	conformation and reactivity	A 3.7	QUIZ 2
9/23	same	A 3.7
9/25	Baldwin's rules	A 3.9
9/28	basic thermodynamics	A 4.1
9/30	problems/help	-
10/1	EXAM 1		EXAM 1
10/2	intro to paper topics, kinetics	A 4.2
10/5	mo better kinetics	A 4.2
10/7	kinetic isotope effects	A 4.5
10/9	linear free energy relationships	A 4.3
10/12	K vs T control, Hammond	A 4.4	QUIZ 3
10/14	acid/base catalysis, topics due	A 4.8,9
10/16	Long Weekend
10/19	solvent effects	A 4.10
10/21	problems/help -
10/22	EXAM 2		EXAM 2
10/23	NaBH₄/LiAlH₄	B 5.2
10/26	stereochemistry of hydride redxn	B 5.2
10/28	reduction of other functionality	B 5.2
10/30	other sources of hydride	B 5.2
11/2	radicals, initiation and structure	A 12.1,2
11/4	Bu₃SnH & SmI₂ reduction of RX	B5.4
11/6	addition of radicals to alkenes	B 10.3	QUIZ 4
11/9	as above	B 10.3
11/11	help session for student papers
11/13	Huckel MO theory for polyenes	A 1.3-5
11/16	intro to pericyclic reactions	A 11 intro
11/18	electrocyclic reactions	A 11.1
11/19	EXAM 3		EXAM 3
11/20	electrocyclic reactions	A 11.2
11/23	sigmatropic rearrangements	A 11.2
11/25	Thanksgiving
11/27	Thanksgiving
11/30	Diels-Alder reaction	A 11.3, B 6.1
12/2	same	same
12/4	design of multistep syntheses	B 13.3	RESEARCH PAPERS DUE
12/7	natural product synthesis	B 13.4
12/9	same	we'll see
12/11	same	time will tell
12/14 through 12/18	FINAL EXAMINATIONS		FINAL EXAMINATIONS

CHEM 44098 LAB SCHEDULE

Date	Topic	Points	Writeup due
9/3	check in
9/10	Enantioselective Reduction By Yeast of Acetoacetic Esters (start in class on 9/7)	35	9/24
9/17	finish yeast reductions
9/24	Reduction of 4-tert-Butylcyclohexanone with Various Hydride Sources	35	10/8
10/1	finish hydride reductions (after Exam 1)
10/8	Synthesis of Substituted Benzyl Ethers (start in class on 10/7)	45	10/29
10/15	continuation of above
10/22	finish above (after Exam 2)
10/29	Linear Free Energy Relationships and the DDQ Oxidation of Substituted Benzyl Ethers	35	11/12
11/5	as above
11/12	Synthesis of the 1,3-Thiazoline of Cinammonitrile (start in class on 11/11)	35	12/10
11/19	Exam 3 (no lab)
11/26	Thanksgiving
12/3	purification of the aforementioned thiazoline
12/10	check out

The lab component of your overall course grade is 200 out of the total of 850 possible points. In addition to the points listed above, you will also be graded (total 15 points) on general lab performance in the following areas: coming to lab prepared (including the appropriate readings from the 220-221 lab manual), coming to lab on time, doing the lab work in a safe and courteous manner. Writeups will be done in the same format as writeups from Chem 221. Any deviations or additions to the writeup format will be noted in the handout associated with each experiment.

Back to the Chemistry Department Home Page!

Last updated September 16, 1998.
The URL for this page is http://lyco2.lycoming.edu/dept/chem/fall1998/440syl.htm

quizzes	60 points
exam 1	100 points
exam 2	100 points
exam 3	100 points
final exam (cumulative)	150 points
laboratory	200 points
student paper	60 points
homework	80points
total	850 points