CHEMISTRY  261L

(CHE  261L)

 

ORGANIC  CHEMISTRY  II  /  LABORATORY

 

"Welcome  Back  to  What  You  Love  Experimenting:

CHEMISTRY!!!"

 

 

Spring  Semester  2005

 

1:10 PM - 5:00 PM (01L)                Wednesday

8:10 AM - 12:00 Noon (02L)          Tuesday

Jennings Hall 325 (JE 325)

 

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  OBJECTIVE  AND  DESCRIPTION

 

            YOU CANNOT SERIOUSLY CONSIDER LEARNING ABOUT SCIENCE WITHOUT PRACTICING IT.  Well, if there is A SCIENCE that especially requires practicing it in order to seriously learn about it, this is CHEMISTRY for sure!  Also, if there is A SCIENCE that is AN EXPERIMENTAL SCIENCE, this is CHEMISTRY for sure!

            Well, still need to be convinced about the necessity of a 100% experimentally-oriented laboratory course such as CHEMISTRY 261L?????!

            The main objective of CHEMISTRY 261L is to 1) "consolidate", and 2) expand your knowledge of Organic Chemistry acquired in the "Organic Chemistry II" lectures via the PRACTICE of Organic Chemistry;  especially the PRACTICE of Synthetic Organic Chemistry.

            The primary focus of CHEMISTRY 261L is mostly on the use of the basic experimental techniques learnt last semester for the preparation, the purification, and the analysis of the products of a wide variety of organic reactions.

            For the most part of CHEMISTRY 261L, we will concentrate our efforts on the synthetic and mechanistic aspects of a wide variety of organic chemistry, using the techniques learnt last semester, with the goal of illustrating and bringing together as many of the concepts from the "Organic Chemistry II" lectures as possible.

            Spectroscopy, a mean to gather information about the structure of molecules by making physical measurements on compounds, will be systematically used.

 

OTHER  REMARKS  OF  GENERAL  INTEREST

 

            Arrive at lab ready to do chemistry!!!  Preparation for the laboratory includes reading the laboratory procedure (handout) and supporting material (if any), and preparing your notebook in advance.

            Pre-lab discussions will be kept to "a minimum".  Post-lab discussions will be occasionally conducted to ensure that the key points of the exercises (the experiments!) were understood, to generalize the concepts beyond the specific examples used, and will always conclude with the post-laboratory question sheets.

            Laboratory is scheduled for a ca. four (4) hour period.  Realize that the time needed to complete the laboratory will depend on the actual experiment and your preparedness.

 

ATTENDANCE  POLICY

 

            Attendance is required.  If you must miss a lab, you must be excused by me, OJ-CN.  A legitimate excuse for missing a lab "can be" illness.  Other situations may also be considered legitimate (by me).  If you must miss a lab, contact me as soon as possible after the lab (within one day) or, if possible, let me know before the lab.  If you miss a lab and do not contact me within one day, you will receive zero points for both the post-laboratory question sheet and the laboratory report.  Under NO circumstances will you be allowed to miss more than two (2) labs.

 

SAFETY  CONSIDERATIONS

 

            There is only one kind of laboratory - one that is safe, clean, well organized, and in an environment conducive to learning;  and discovery!  This is the kind of laboratory which must be run in this course.  Students not dressed properly or prepared properly will NOT be permitted into the laboratory.

 

            € Protective eye covering in the form of APPROVED safety goggles or safety glasses must be worn in the laboratory at ALL times.  The use of contact lenses is highly not advisable.  Sun glasses are not acceptable.

            € Proper attire is mandatory, as is strict attention to all safety guidelines at all times.  Closed toe shoes or boots, socks and long pants are required.  Shirts must cover the midsection.  Aprons or lab coats are recommended.

            € Eating, drinking, or smoking are never permitted in the laboratory.

 

REQUIRED  SUPPLIES

 

            € You will receive handouts detailing the experimental procedure you will

               follow for each lab.

            € Approved safety goggles or safety glasses.

            € Bound laboratory notebook (use the one from last semester!).

 

"STRONGLY  RECOMMENDED  SUPPLIES"

 

            € "A minimum of interest" in experimental chemistry.

            € Some manual dexterity.

            € And some good common sense.

 

OPTIONAL  SUPPLIES

 

            € Lab coat OR apron.

 

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.

 

CHEMISTRY 261L  FORMAT

 

            The laboratory contribution (CHE 261L) to the final grade in CHEMISTRY 261 is ca. 30% of the Total Points.  Thus, the laboratory makes a greater contribution to the final course grade than does any single examination.  The laboratory can offset a low examination grade in CHE 261.  The laboratory work is dependent mostly on individual efforts and dedication of the students to writing good reports at their own convenience.  Thus, the laboratory grade is dependent on effort as well as mastery of specific techniques.  The laboratory grade is a cumulative average based on the laboratory notebook (20 Points), the laboratory reports (200 Points), and the post-laboratory question sheets (55 Points) as indicated below.

            With this being said, 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 (0.60 x 275pts) in the present case (CHE 261L);      a piece of cake, believe me!

 

            € Laboratory Notebooks.                          20 Points (7% of Lab Points)

 

            Laboratory notebooks will not be systematically collected -and graded- at the end of each laboratory session.  However, you will be required to maintain a "research quality" laboratory notebook.  I will keep an eye on the "maintenance" of laboratory notebooks during the course of the laboratory sessions, but I may also collect laboratory notebooks once during the course of the semester, and write some comments in them ­if necessary!

            Laboratory notebooks will be definitely 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, and you may receive up to a total of 20 Points.  They will be returned to you on Final day.

            The "minimum required information" -that would come to anybody's mind- to "CLEARLY & CLEANLY" include in your laboratory notebook is:

 

                        ® Title of the experiment.

                        ® Date.

                        ® Reference to the experimental procedure.

                            (cite "handout" [affix the handout into your notebook], or any other

                             distributed information)

                        ® Chemical reaction to be performed (write it when any),

                            or A brief statement of objective if no reaction is involved.

                        ® A table of Reagents and Solvents with actual amounts (g, mg, L, mL)

                            and calculated numbers of moles (mol) or millimoles (mmol),

                            including their physical properties (when indicated in handout).

                        ® Record of any pertinent observations.

                        ® Record of all collected, required data.

 

            € Laboratory Reports.                                200 Points (73% of Lab Points)

 

            The laboratory reports will consist of a combination of FULL and PARTIAL laboratory reports.  With a total of ten (10) laboratory reports for a total of twelve (12) laboratory experiments, there should be five (5) of each type.  FULL laboratory reports will be worth 25 Points while PARTIAL laboratory reports will be worth 15 Points.

            The PARTIAL laboratory reports should ONLY contain the information that is requested on the laboratory report sheet that is handed for each experiment.

            The FULL laboratory reports will serve as the place to 1) state the goal(s) of the experiment, 2) describe the procedure that you used, 3) turn-in your experimental results, 4) discuss your results and some collected -or given- analytical data, and       5) draw some conclusions.  They should be clearly written and presented (i.e., word processed).  NEATNESS COUNTS!!!  Proper scientific language and English usage and content are mandatory in all FULL laboratory reports.  Do not repeat word for word the theory or procedures given in the handouts or supporting material.  This is PLAGIARISM, and anyways I know what is said in these materials.  Describe the procedure in your own words.

            Proper reports must be based on the exact data obtained in the experiment.  No report however well written will be accepted, if the appropriate data is not used.  Scrupulous honesty in reporting results is crucial in any scientific investigation no matter how apparently insignificant the study may be.  Part of the training in chemistry is the reporting of all results honestly.

            The information to "CLEARLY & CLEANLY" include in your FULL laboratory report is:

 

                        ® Title of the Experiment.

                        ® Name of the Experimenter.

                        ® Date of Submission of the Report.

                        ® Purpose of the Experiment.

                        ® Introduction.

                        ® Procedure.

                        ® Data and Results.

                        ® Discussion of Results.

                        ® Conclusions.

 

            ® Purpose of the Experiment.

            No more than ONE (1) PARAGRAPH, double-spaced.

 

            It should briefly and succintly indicate the goal(s) of the experiment.  Elaboration is NOT needed here.

 

            ® Introduction.

            No more than ONE AND A HALF (1.5) PAGE, double-spaced.

 

            It should include important theoretical and historical material which is relevant to the experiment.  Here the student should check the course textbook and the experiment supporting material (if any).  Reaction equations, if appropriate, giving the reactions involved should be included here.

 

            ® Procedure.

            No more than TWO (2) PAGES, double-spaced.

 

            It should represent the exact methods, contain the exact amounts, and report the exact information used by the student.  It should be written in the past tense, and in the passive voice and should include all details followed.  This section should be written in paragraph style.  One should be able to repeat the experiment in exact detail from the procedure written.

 

            ® Data and Results.

            No more than ONE AND A HALF (1.5) PAGE, double-spaced.

 

            It should include raw data, calculations, and all graphs and charts.  The material in this section should be presented lucidly so that the calculations can be followed rapidly.  Clearly presented and labeled sample calculations should be included in this section.  For all experiments in which a product is formed, a mass should be reported, and a % yield should be calculated based upon the amount of starting material used.

 

            ® Discussion of Results.

            No more than ONE (1) PAGE, double-spaced.

 

            It should provide an interpretation of the information from the section on Data and Results.  In this section, students should draw from the theoretical material presented in the introduction and relate this to the results obtained.  This section should offer possible explanations for the results obtained.  Some discussion of error (if any) should be included.

 

            ® Conclusions.

            No more than ONE (1) PARAGRAPH, double-spaced.

 

            It should summarize final results, should relate to the original purpose of the experiment, and should very briefly indicate whether or not the purpose of the experiment was achieved.

 

            € Post-laboratory Question Sheets.         55 Points (20% of Lab Points)

 

            The post-laboratory question sheets will serve as the place to -hopefully!- show your -hopefully!- true understanding of the experiment of the day.

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

            Each post-laboratory question sheet will be worth 5 Points.

 

            € Important Remarks about Laboratory Reports and Post-laboratory Question Sheets.

 

            You should know the names and structures of most of the compounds you worked with (unless told otherwise), know all the reactions carried out along with their mechanism, know the reagents needed, and -of course!- know how to use the analytical tools that we have learnt last semester (IR, MS, NMR, GC, and TLC).  You are also expected to know WHY various procedures were followed, WHY certain side products were or were not formed.  This listing is not meant to be all inclusive, but is given to provide a basis for your studying, ...and your understanding of what "takes place" in JE 325!

 

GRADING  POLICY

 

            Unofficial cut-offs for the laboratory course as a whole (CHE 261L) will be in the vicinity of (275 Points Total):

A+   „95% (261pts)        A   „90% (247pts)        A­   „85% (233pts)        B+   „78% (214pts)

B   „73% (200pts)        B­   „68% (187pts)        C+   „61% (167pts)        C   „56% (154pts)

C­   „51% (140pts)        D+   „44% (121pts)        D   „39% (107pts)        D­   „34% (93pts)

F          <34% (really bad!)

 

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 writing of laboratory reports.  Identically written lab reports are unacceptable, and if you are caught plagiarizing, it will be reflected in the grade.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

LABORATORY  SCHEDULE

 

            PARTIAL Laboratory Reports are due for laboratory experiments that are underlined (date), and FULL Laboratory Reports are due for laboratory experiments that are italicized (date).

 

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!