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.
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 
acyclic conformational analysis A 3.1,2 
9/16  conf. analysis of carbocycles  A 3.3,4 
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 
NaBH4/LiAlH4  B 5.2 
10/26  stereochemistry of hydride redxn  B 5.2 
reduction of other functionality  B 5.2 
10/30  other sources of hydride  B 5.2 
radicals, initiation and structure  A 12.1,2 


Bu3SnH & SmI2 reduction of RX   B5.4
addition of radicals to alkenes  B 10.3  QUIZ 4 
11/9  as above  B 10.3
 help session for student papers 
11/13  Huckel MO theory for polyenes  A 1.3-5 
 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 
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 
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
finish hydride reductions (after Exam 1)  
10/8  Synthesis of Substituted Benzyl Ethers (start in class on 10/7) 45 
10/15  continuation of above
10/22  finish above (after Exam 2)
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.

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