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 2004
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), 322-0592 (home) [call up to 10pm]
Email: mcdonald@lycoming.edu
Texts and other stuff
a. Advanced Organic Chemistry, Part A, fourth 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), Please note: programmable calculators may not be used during quizzes and exams
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 (McMurry)
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, 2:00 PM, 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!). A key will be posted immediately after class. No late homework will be accepted.
Laboratory - 8:00 - 11:50 AM, Thursday, in the Swing Lab, the labs will be designed to probe mechanistic problems in organic chemistry.
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 660 points. The points will be distributed as follows:
quizzes 45 points
exam 1 100 points
exam 2 100 points
exam 3 100 points
final exam (cumulative) 125 points
laboratory 130 points
homework 60 points
total 660 points
b. Assignment of letter grades is based on the following scale: 660 -594 A, 593 - 528 B, 527 - 462 C, 461 - 396 D, < 395 F. I reserve the right to curve the grades in your favor 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 (appropriately weighted). 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 (12 points max).
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.
Chem 44004 Schedule
Date Topic Reading Assignment Quiz/Exam
8/30 This is Advanced Organic Chemistry A, the preface
9/1 enantiomerism A 2.1
9/3 diastereomerism and resolution A 2.1
9/6 diastereomerism and resolution A 2.2
9/8 dynamic stereochemistry A 2.3
9/10 prochirality A 2.4 Quiz 1
9/13 acyclic conformational analysis A 3.1,2
9/15 conformational analysis of cyclic compounds A 3.3-5
9/17 conformation and reactivity A 3.7
9/20 conformation and reactivity A 3.7
9/22 Baldwin's rules A 3.9 Quiz 2
9/24 kinetic isotope effects A 4.5
9/27 kinetic isotope effects A 4.5
9/29 problems/help -
9/30 - - Exam 1
10/1 acid/base catalysis A 4.8,9
10/4 linear free energy relationships A 4.3
10/6 linear free energy relationships A 4.3
10/8 redox conventions handout
10/11 NaBH4/LiAlH4 B 5.2
10/13 stereochemistry of hydride reduction B 5.2, A 3.10
10/15 Long Weekend
10/18 reduction of other functionality with hydride B 5.2 Quiz 3
10/20 other sources of hydride B 5.2
10/22 a deprotonation of carbonyls B 1.1,2
10/25 alkylation of enolates B 1.4
10/27 more alkylation issues B 1.5-7
10/29 radicals: initiation and structure A 12.1,2
11/1 Bu3SnH and SmI2 reduction of RX B 5.4
11/3 problems/help -
11/4 - - Exam 2
11/5 addition of radicals to alkenes B 10.3
11/8 addition of radicals to alkenes B 10.3
11/10 Huckel MO theory for polyenes A 1.3-5
11/12 as above A 1.3-5
11/15 intro to pericyclic reactions A 11 intro
11/17 electrocyclic reactions A 11.1
11/19 electrocyclic reactions A 11.2
11/22 sigmatropic rearrangements A 11.2
11/24 Thanksgiving
11/26 Thanksgiving
11/29 Diels-Alder reaction A 11.3, B 6.1
12/1 more DA
12/2 - Exam 3
12/3 more DA
12/6 natural product synthesis B13.3,4
12/8 same chemical literature
12/10 same chemical literature
12/13-12/17 finals week
CHEM 44004 LAB SCHEDULE
Date Topic Points Writeup due
9/2 check in
9/9 Exp. 1: Reduction of 4-tert-Butylcyclohexanone with 30 9/23
Various Hydride Sources (the reaction)
9/16 as above (purification and characterization)
9/23 Exp. 2: Synthesis of Substituted Benzyl Ethers 30 10/21
(the reaction)
9/30 exam 1
10/7 Synthesis of Substituted Benzyl Ethers
(purification)
10/14 as above (characterization)
10/21 Exp. 3: Linear Free Energy Relationships and the 25 10/29 (calculations due 10/25)
DDQ Oxidation of Substituted Benzyl Ethers
10/28 Exp. 4: Synthesis of Deuterium Labeled Benzyl 30 11/22 (in class)
Ethers (the reaction)
11/4 exam 2
11/11 Synthesis of Deuterium Labeled Benzyl Ethers
(purification)
11/18 as above (characterization)
11/25 Thanksgiving
12/2 exam 3
12/9 Exp. 5: Kinetic Isotope Effects and the DDQ 15 final exam
Oxidation of Labeled Benzyl Ethers, check out
The lab component of your overall course grade is 130 out of the total of 660 possible points. Writeups will be done in the same format as in Chem 221. Any deviations or additions to the writeup format will be noted in the handout associated with each experiment.
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