CHEMISTRY  500

 

ADVANCED  ORGANIC  CHEMISTRY  I

 

³Welcome  to  the  Class  that  Tells  You  Everything

that  You  Have  Always  Wanted  to  Know,

but  Were  Afraid  to Ask,

about  ORGANIC  CHEMISTRY!!!²

 

Spring  Semester  2005

5:30 - 8:00 PM     Thursday  ­  Jennings Hall 306 (JE 306)

 

Olivier J.-C. Nicaise, Ph.D., Professor of Potions and Elixirs

Office:  327 Jennings Hall         Laboratories:  329 & 325 Jennings Hall

Phone:  (203) 392-6271     Home:  (203) 230-8466     E-mail:  nicaiseo1@southernct.edu

 

COURSE  DESCRIPTION

            You are here to learn the advanced, subtle science and exact art of potion- and elixir-making (a.k.a organic chemistry).  In that respect, CHEMISTRY 500 is a continuation of Introductory Organic Chemistry, i.e. the study of the chemistry of carbon containing compounds, but it is not a review or an expansion on subjects covered in the introductory course.  There are indeed excellent reasons not to emphasize review of basic material in an advanced course!  This is why we will early introduce ³advanced² topics ­topics that are not usually stressed in first-year courses.  Well, this class is designed to increase both your understanding and knowledge of Organic Chemistry, particularly from a Physical Organic Chemistry viewpoint, but also with a Synthetic Organic Chemistry taste.  As there is little foolish wand-waving here, many of you will hardly believe this is magic;  but it is!

            It is expected that everyone enrolled in this course has a working understanding of the material covered in CHE 260 & CHE 261 (or the equivalent) .

 

REQUIRED  SUPPLIES

            € Advanced Organic Chemistry:  Reactions and Mechanisms,

            Second Edition, Pearson Prentice Hall, 2004;  by Bernard MILLER.

            € Solutions Manual for Advanced Organic Chemistry:  Reactions and

         Mechanisms,

            Second Edition, Pearson Prentice Hall, 2004;  by Bernard MILLER.

 

OFFICE  HOURS

            € "OPEN DOOR" policy at all time.

            (That is, if the door is open, feel free to 'knock'.  If the door is closed, I am

            VERY probably in the Laboratories (JE 329 or JE 325);  so, come & see me!).

            € AT FIXED HOURS:           Thursdays, right after class, 8:00 - 9:00 pm

            € Office hours may also be held by appointment.

 

CHEMISTRY  500  FORMAT

 

            € In-Class Exams.                                        450 Points (100% of Total Points)

            The grading in the course will come solely from the in-class examinations.  There will be THREE in-class exams, all of equal value (each in-class exam will be worth 150 Points).  The last in-class exam will not be comprehensive.  Also, ±20% of each in-class exam will be problems chosen from the list of "Strongly Suggested Problems² (SSP) to do given in class, and taken from our textbook.  The three in-class exams will be administered according to the schedule indicated below.

 

                                    Exam #1         THURSDAY, March 3, 2005 ­ Lectures 1-4

                                    Exam #2         THURSDAY, April 14, 2005 ­ Lectures 5-8

                                    Exam #3         THURSDAY, May 19, 2005 ­ Lectures 9-12

 

            In-class exams MUST be taken at the indicated time, except for medical emergencies for yourself or for immediate family, and business-related travel.  As a rule, MAKE-UP EXAMS WILL NOT BE GIVEN.  If you know in advance that you will not be able to sit for an exam, PLEASE SEE ME as soon as possible.

            Exam papers will be returned during lecture time, and any request for a re-grade will have to be made within a TWO (2)-WEEK period following the return date.

 

            € Grading Policy.

            Cut-offs for exams and the course as a whole will be in the vicinity of:

            A+       „95%              A         „90%              A­       „85%              B+       „78%

            B         „73%              B­       „68%              C+       „61%              C         „56%

            C­       „51%              D+      „44%              D         „39%              D­       „34%

F          <34%

            In other words, if you are targeting an A in this course, you will need to achieve at least 0.90 x 450 = 405 Points of the 450 Total Points available in this course;  got it???  GREAT!!!

 

ACADEMIC  IMPROPRIETY

            This polished euphemism needs to be brought up.  'Cheating' (and I hate to use this term, especially at this august institution) of any kind will not be tolerated, because it degrades the principle of meritocracy.  Specific application to this course will largely cover the taking of exams and submission of exams for regrading.

            Verifiable improprieties while taking an exam (such as using unauthorized notes, or blatant examples of 'information exchange') will result in your receiving a mark of zero for that exam.  The same holds true for submitting a forged or tampered exam for regrading.  Your graded exams may be photocopied for purposes of verification prior to being returned to you.

            A second incidence will result in your receiving a failing grade for the course, and the episode brought to the attention of the Dean of the Graduate School (this is not good).

            Further information and specific policies regarding academic impropriety at the University may be found in the Student Handbook and other University publications.

 

STUDENTS  WITH  DISABILITIES

            Students with disabilities who believe that they may need accomodations in this class are asked to contact the Disability Resource Center, located in Engleman Hall B 222 (EN B 222), at (203) 392-6828 or (203) 392-6131 as soon as possible to better ensure that such accomodations are implemented in a timely fashion.

            However, if you would like to speak with me about accomodations, or other concerns, such as emergency medical information, or arrangements in case the building must be evacuated, please make an appointment as soon as possible.  My office location is in Jennings Hall, room 327.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

LECTURE  OUTLINE

            The following is a detailed outline of the material that we should cover this semester in lecture.

 

 

Unit #1:          INTRODUCTION

            A. Mechanisms of Reactions.

            B. Electron Delocalization and Resonance                                                           1

 

Unit #2:          PERICYCLIC REACTIONS

            A. Electrocyclic Reactions                                                                           2

            B. Cycloaddition and Cycloreversion Reactions                                     3

            C. Sigmatropic Reactions                                                                            4

 

Unit #3:          LINEAR FREE-ENERGY RELATIONSHIPS

            A. The Hammett Equation                                                                         5.1

 

Unit #4:          ELECTRON-DEFICIENT INTERMEDIATES

            A. Carbocations                                                                                           6.1 ­ 6.4

            B. Migrations to Nitrogen and Oxygen                                                    6.5

            C. Neighboring Group Effects and ³Nonclassical² Cations                              7 (in part)

 

Unit # 5:         ELECTRON-RICH & ELECTRON-NEUTRAL INTERMEDIATES

            A. Carbanions                                                                                                          8.1

            B. Free Radicals                                                                                            8.2

 

Unit # 6:         OTHER ELECTRON-DEFICIENT INTERMEDIATES

            A. Carbenes, Carbenoids, and Nitrenes                                                  9 (in part)

 

 

 

 

 

HAVE  A  GREAT  SUMMER !!!!!