CHEMISTRY  261  (01L, 02L)

 

ORGANIC  CHEMISTRY  II

 

³Welcome  Back  to  the  Class  You  Love!!!²

 

Spring  Semester  2005

12:10 - 1:00 PM   MWF  ­  Jennings Hall 335 (JE 335)

 

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 keep learning the subtle science and exact art of potion- and elixir-making (a.k.a organic chemistry).  In that respect, CHEMISTRY 261 is a continuation of CHEMISTRY 260, i.e. the study of the chemistry of carbon containing compounds.  We will continue to investigate the transformation of the major functional groups with the same -actually more!- emphasis than last semester on reaction mechanisms and stereochemistry -oh yes we will!  There will be also a special emphasis on the development of synthetic schemes.  As there is little foolish wand-waving here, many of you will hardly believe this is magic;  but it is!

            The laboratory component of this course (CHE 261L) will rely heavily on the numerous techniques which were learnt last semester in order to prepare, purify, and analyze the products of a wide variety of organic reactions.  Spectroscopy will be systematically used.

            It is expected that everyone enrolled in this course has a working understanding of the material covered in CHE 120 & CHE 121 (or the equivalent) and in CHE 260.

 

REQUIRED  SUPPLIES

            € Organic Chemistry:  Structure and Reactivity, Fifth Edition,

            Houghton Mifflin Company, 2004;  by Seyhan N. EGE.

            € Study Guide for Organic Chemistry:  Structure and Reactivity,

            Fifth Edition, Houghton Mifflin Company, 2004;  by Seyhan N. EGE,

            Roberta W. KLEINMAN, and Peggy ZITEK.

 

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:           Tuesdays, 2:00 - 4:00 pm

                                                            Thursdays, 10:00 am - 12:00 noon

                                                            Fridays, 10:00 am - 11:00 am

            € Office hours may also be held by appointment.

 

CONFERENCES

            Conferences are optional problem-solving sessions that will be held on FRIDAY afternoons, at 1:30 PM, in Jennings Hall 306 (JE 306).  Conference sheets will be handed in class on Fridays (or on Mondays), and we will work on the problems TOGETHER on the following Fridays;  therefore, you will have approximately a week to prepare before coming to a Conference.  An active participation of the "audience" is required:  in other words, I will typically do ONE problem of a type in order to demonstrate the reasoning that is necessary to solve this type of problem, and "some members of the audience" will then volunteer to go to the board and do the other problems.  A detailed answer sheet will be kept on reserve at the library following each Conference.

 

A  LITTLE  BIT  OF  ADVICE  -same as I told you last August!

 

Keep re-drawing these mechanisms!

 

            Learning potion- and elixir-making is very much like learning to speak a foreign language, to play an instrument, to play soccer well, ...or like winning gold at the Olympics!  It takes time, and practice, and more practice.  The keys to success in a course like this -or any of your college courses!- involves a little bit of discipline, and a little planning.

€ Set some time aside EACH DAY to do organic chemistry.

€ Work all of the exercises!  Work all of the exercises!  Work all of the exercises!

Contrary to conventional belief, organic chemistry is not all memorization.

€ Avoid falling behind in the reading.

€ Attend most of the lectures, if not all.

€ Review the material after each lecture.

 

CHEMISTRY  261  FORMAT

 

            € Hourly Exams.                                          450 Points (~49% of Total Points)

            FOUR hourly exams will be administered.  Each hourly exam will be worth 150 Points, and the LOWEST SCORE of the four hourly exams will be dropped.  Also, ±10% of each hourly exam will be problems chosen from the list of "Strongly Suggested Problems² (SSP) to do given in class, and taken from our textbook.  The four hourly exams will be administered during WEDNESDAY or MONDAY class time according to the schedule indicated below.

 

                                    Exam #1         WEDNESDAY, February 16, 2005

                                    Exam #2         WEDNESDAY, March 16, 2005

                                    Exam #3         MONDAY, April 18, 2005

                                    Exam #4         MONDAY, May 9, 2005

 

            Hourly Exams MUST be taken at the indicated time.  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.

 

            € Cumulative Final Exam.             200 Points (~21% of Total Points)

            The Final Exam will be worth a total of 200 Points and cannot be dropped.

            As a Final Exam, we will use the standardized ACS Division of Chemical Education Examination in Organic Chemistry.  This will be administered during the regularly scheduled Finals period.

 

THURSDAY, MAY 19, 2005:  3:00 ­5:00 PM

 

            € Laboratory.                                               275 Points (~30% of Total Points)

            Laboratory sessions are discussed in more detail in a separate laboratory syllabus (CHE 261L).  Although we will not have a specific lab test, questions which focus on the lab exercises will occasionally appear in the Hourly Exams.

            The lab points will be distributed on the basis of the following criteria:

            ­ Laboratory Reports.

            There will be ten (10) laboratory reports for a total of twelve (12) laboratory experiments.

            The laboratory reports will count for 73% of the lab points.

            ­ Post-laboratory Question Sheets.

            There will be eleven (11) post-laboratory question sheets for a total of twelve (12) laboratory experiments.

            The post-laboratory question sheets will count for 20% of the lab points.

            ­ Laboratory Notebooks.

            Laboratory notebooks will be collected on the last week of laboratory (week of May 2, 2005), or can be turned in at the very latest on the last day of class, i.e. May 11, 2005.  You may receive up to a total of 7% of the lab points.  They will be returned to you on Final day.

            IMPORTANT REMARK, PLEASE TAKE NOTE:

            Chemistry Department policy requires that students taking courses which include lecture AND laboratory MUST PASS THE LABORATORY in that course in order to PASS THE COURSE, regardless of the average grade received in lecture.

            A passing grade for the LABORATORY in that course requires that you achieve AT LEAST 60% of the lab points in that course, that is to say a minimum of 165 Points in the present case (CHE 261);  a piece of cake, believe me!

 

            € 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 + 200 + 275 = 925) = 832.5 Points of the 925 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 a Dean of the College (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 will cover this semester in lecture.

 

Unit #1:          FUNCTIONAL GROUPS AS A BASIS FOR STUDYING REACTIONS

                        AND SYNTHESIS

            A. Alkenes                                                                                         8;  25.6;  19.2;  19.3;

                                                                                                                        19.5

            B. Alkynes                                                                                         9

            C. Polyenes                                                                                       18;  21.6

            D. The Chemistry of Aromatic Compounds.

Electrophilic Aromatic Substitution                                        10;  Sulfonation;

                                                                                                                        14.3.B;  21.7

            E. Alcohols, Diols, and Ethers                                                        13

 

Unit #2:          NUCLEOPHILIC ADDITION TO C sp2

            A. Aldehydes and Ketones.

Addition Reactions at Electrophilic Carbon Atoms              14

 

Unit #3:          NUCLEOPHILIC SUBSTITUTION AT C sp2

            A. Carboxylic Acids and Their Derivatives.

Acyl-Transfer Reactions                                                                        15

 

Unit #4:          ENOLATES, CONDENSATION REACTIONS,

                        & CONJUGATE ADDITION REACTIONS

            A. Enols and Enolate Anions as Nucleophiles.

Alkylation and Condensation Reactions                                            17

 

Unit # 5:         ³A FEW MORE REAGENTS, A FEW MORE REACTIONS²!

            A. Synthesis                                                                                      21.1;  21.2;  21.3;

                                                                                                                        21.4;  21.5

HAVE  A  GREAT  SUMMER !!!!!

 

LABORATORY  OUTLINE

            The laboratory component of this course (CHE 261L) will rely heavily on the numerous techniques which were learnt last semester in order to prepare, purify, and analyze the products of a wide variety of organic reactions.

            If you know in advance that you will not be able to come to your laboratory session, PLEASE SEE ME as soon as possible.  Non-reported absenses occasioned by illness or other legitimate reasons are excused by a memo from a physician or a Dean;  non-reported unexcused absenses will result in a zero.

            The lab schedule is as follows:

 

Week of . . .                                              Experiment

January 31st                                             HELLO AGAIN!  HAPPY NEW YEAR!  CHECK-IN

                                                                        #1 ­ Separation by Gas Chromatography (GC)

February 7th                                           #2 ­ Markovnikov Addition:  THP Ether Formation

February 14th                                        #3 ­ Anti-Markovnikov SYN Addition - Hydroboration/Oxidation

February 22nd                                        #4 ­ Diels-Alder Reaction:

                                                                                          4-Cyclohexene-cis-1,2-dicarboxylic Acid Anhydride

February 28th                                        #5 ­ Oxidation of an Alcohol by a Chromate-Impregnated Resin:

                                                                                          9-Fluorenone

March 7th & 14th                               #6 ­ An Oxidation-Reduction Scheme:

                                                                                          Part I:  Bleach Oxidation of L-(­)-Borneol to Camphor

                                                                        #7 ­ An Oxidation-Reduction Scheme:

                                                                                          Part II:  NaBH4 Reduction of Camphor to Isoborneol

March 21st                                               SPRING BREAK!

March 28th                                              #8 ­ Grignard Addition to a Ketone and an Ester:  Triphenylmethanol

April 4th                                                  #9 ­ Aldol Condensation:  Dibenzalacetone

April 11th                                                #10 ­ Wittig Olefination:  Synthesis of 1,4-Diphenyl-1,3-Butadiene

April 18th & 25th                               #11/Part I & II ­ Grignard Addition to a Bis-Ester:

                                                                                          Temperature-Dependent Outcome of the Tetrahedral Intermediate

May 2nd                                                     #12 ­ Synthesis of a Chemiluminescent Substance:  Luminol

                                                                        CHECK-OUT;  GOODBYE!  HAVE A GREAT SUMMER!