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.

Fall 2002       Advanced Organic Chemistry 440               Lycoming College

Lycoming College                  Chem 440                                           Fall 2002

                                        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 Afourth 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 (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 670 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                                                                        140 points

            homework                                                                         60 points

            total                                                                                 670 points


b.         Assignment of letter grades is based on the following scale:  670 -603 A, 602 - 536 B, 535 - 469 C, 468 - 402 D, < 401 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 44002 Schedule


Date     Topic                                                               Reading Assignment      Quiz/Exam

8/26     This is Advanced Organic Chemistry                 A, the preface

8/28     enantiomerism                                                   A 2.1

8/30     diastereomerism and resolution              A 2.1


9/2       diastereomerism and resolution              A 2.2

9/4       dynamic stereochemistry                                   A 2.3

9/6       prochirality                                                       A 2.4                           Quiz 1


9/9       acyclic conformational analysis              A 3.1,2

9/11     conformational analysis of cyclic compounds A 3.3-5

9/13     conformation and reactivity                               A 3.7


9/16     conformation and reactivity                               A 3.7

9/18     Baldwin's rules                                      A 3.9                           Quiz 2

9/20     kinetic isotope effects                                        A 4.5


9/23     kinetic isotope effects                                        A 4.5

9/25     problems/help                                                   -          

9/26     -                                                                       -                                   Exam 1

9/27     linear free energy relationships               A 4.3


9/30     linear free energy relationships               A 4.3

10/2     acid/base catalysis                                            A 4.8,9

10/4     redox conventions                                             handout


10/7     NaBH4/LiAlH4                                     B 5.2

10/9     stereochemistry of hydride reduction                 B 5.2, A 3.10

10/11   reduction of other functionality with hydride       B 5.2                            Quiz 3


10/14   other sources of hydride                                    B 5.2

10/16   a deprotonation of carbonyls                            B 1.1,2

10/18   Long Weekend


10/21   alkylation of enolates                                         B 1.4   

10/23   more alkylation issues                                       B 1.5-7

10/25   radicals: initiation and structure              A 12.1,2


10/28   Bu3SnH and SmI2 reduction of RX                    B 5.4

10/30   problems/help                                                   -

10/31   -                                                                       -                                   Exam 2

11/1     addition of radicals to alkenes                           B 10.3




11/4     addition of radicals to alkenes                           B 10.3

11/6     Huckel MO theory for polyenes                        A 1.3-5

11/8     as above                                                           A 1.3-5


11/11   intro to pericyclic reactions                                A 11 intro

11/13   electrocyclic reactions                                       A 11.1

11/15   electrocyclic reactions                                       A 11.2


11/18   sigmatropic rearrangements                               A 11.2

11/20   Diels-Alder reaction                                          A 11.3, B 6.1

11/21   -                                                                       -                                   Exam 3

11/22   same                                                                same                           


11/25   same                                                                -                                              

11/27   Tgiving

11/29   Tgiving


12/2     natural product synthesis                                   B13.3,4

12/4     same                                                                same

12/6     same                                                                same


12/9 -12/13      finals week


             CHEM 44002 LAB SCHEDULE

Date        Topic                                                                                      Points                     Writeup due

8/29         check in                                                                                                


9/5           Exp. 1:  Reduction of 4-tert-Butylcyclohexanone with  30                             9/19

Various Hydride Sources (the reaction)


9/12         as above (purification and characterization)


9/19         Exp. 2:  Synthesis of Substituted Benzyl Ethers               30                          10/17

                (the reaction)


9/26         exam 1


10/3         Synthesis of Substituted Benzyl Ethers                                                          



10/10       as above (characterization)


10/17       Exp. 3:   Linear Free Energy Relationships and the          25                          10/25 (in class)

                DDQ Oxidation of Substituted Benzyl Ethers


10/24       Exp. 4:  Synthesis of Deuterium Labeled Benzyl              30                          11/25 (in class)

                Ethers (the reaction)


10/31       exam 2


11/7         Synthesis of Deuterium Labeled Benzyl Ethers



11/14       as above (characterization)                                                                                               

11/21       exam 3


11/28       Thanksgiving


12/5         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 140 out of the total of 670 possible points.  In addition to the points listed above, you will also be graded (total 10 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 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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Last updated August 29, 2002.
The URL for this page is http://www.lycoming.edu/chem/fall2002/440syl.htm