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 2000

                                        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,  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)

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,  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 740 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)         120 points

            laboratory            140 points

            student paper     60 points

            homework          60 points

            total                                                               740 points


b.         Assignment of letter grades is based on the following scale:  740 -666 A, 665 - 592 B, 591 - 518 C, 517 - 444 D, < 444 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.   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 (15 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.





















SCHEDULE  CHEM 440, 2000


Date         Topic                                                                       Reading Assignment                              Quiz/Exam

8/28         This is Advanced Organic                                   A, the preface

8/30         polar rxns and enantiomerism                   A 2.1

9/1                enantiomerism                                                          A 2.1


9/4                diastereomerism and resolution                 A 2.2

9/6           dynamic stereochemistry                                        A 2.3

9/8                prochirality                                                              A 2.4                                                        QUIZ 1


9/11         acyclic conformational analysis                   A 3.1,2                    

9/13         conf. analysis of carbocycles                                             A 3.3,4

9/15         conf. analysis of heterocycles                                            A 3.5                                                       


9/18                conformation and reactivity                                      A 3.7                                                        QUIZ 2

9/20         same                                                                        A 3.7

9/22         Baldwin's rules                                                        A 3.9


9/25         kinetic isotope effects                                           A 4.5

9/27                problems/help                                                         -

9/28         -                                                                               -                                                               EXAM 1                           9/29         intro to paper topics, linear free energy                              A 4.3


10/2         more linear free energy relationships                             A 4.3

10/4         kinetic isotope effects                                           A 4.5

10/6         linear free energy relationships                                A 4.3


10/9         K vs T control, Hammond                                    A 4.4                                                        QUIZ 3

10/114     acid/base catalysis, topics due                 A 4.8,9

10/13       solvent effects                                                       A4.10


10/16                NaBH4/LiAlH4                                                         B 5.2                                                                       

10/18                problems/help                                        

10/19       -                                                               -                                                                               EXAM 2

10/20                stereochemistry of hydride redxn                       B 5.2



10/23       reduction of other functionality                  B 5.2

10/25       other sources of hydride                                   B 5.2       

10/27       long weekend                                                 -                                                                                                                              

10/30       radicals, initiation and structure                   A 12.1,2

11/1         Bu3SnH & SmI2 reduction of RX                           B5.4

11/3         addition of radicals to alkenes                   B 10.3                                                      QUIZ 4


11/6         as above                                                                 B 10.3

11/8         help session for student papers                     -

11/10       Huckel MO teory for polyenes                  A 1.3-5



Revised 2nd page to Chem 440, 2000 Syllabus



11/13       intro to pericyclic reactions                                   A 11 intro

11/15                electrocyclic reactions                                              A 11.1

11/16       -                                                                               -                                                               EXAM 3

11/17                electrocyclic reactions                                              A 11.2


11/20                sigmatropic rearrangements                                    A 11.2

11/22                Thanksgiving

11/24                Thanksgiving


11/27       Diels-Alder reaction                                                          A 11.3, B 6.1

11/29       same                                                                        same

12/1         design of multistep syntheses                                  B 13.3     


12/4         natural product synthesis                                     B 13.4

12/6         same                                                                        -                                               RESEARCH PAPERS DUE

12/8         same                                                                        -


12/11 through 12/15  FINAL EXAMINATIONS


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    Last updated September 4, 2000.
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