CHEMISTRY  260  (01L, 02L, 03L)

 

ORGANIC  CHEMISTRY  I

 

Fall  Semester  2004

12:10 - 1:00 PM   MWF    Morrill Hall 103 (MO 103)

 

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 subtle science and exact art of potion- and elixir-making (a.k.a organic chemistry).  In that perspective, CHEMISTRY 260 is the first of a two-part Introductory Organic Chemistry lecture & laboratory course that focuses on the study of the chemistry of carbon containing compounds.  We will investigate the underlying physical principles of the reactions of these compounds.  There will be a special emphasis on bonding theory, acid-base principles, the functional groups, stereochemistry, reaction mechanisms, and 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 260L) will include the development of techniques that are important to the organic chemist, and the subsequent use of these techniques to prepare, purify, and analyze the products of organic reactions.  Spectroscopy, a mean to gather information about the structure of molecules by making physical measurements on compounds, will also be studied early on.

            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).

 

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.

            Molecular Models.

            FlexibleStereoChemistry The flexible molecular model kit.

"STRONGLY  RECOMMENDED  SUPPLIES"

            "A minimum of interest" in chemistry.

            Lots of scrap paper and pens or pencils.

            And some good common sense.

 

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 Research Laboratories (JE 329);  so, come & see me!).

            AT FIXED HOURS:           Tuesdays, 2:00 - 4:00 pm

                                                            Thursdays, 10:00 am - 12:00 noon

            Office hours may also be held by appointment.

 

CONFERENCES

            Conferences are optional problem-solving sessions that will be held on THURSDAY evenings, at 5:30 PM, in Morrill Hall 6 (MO 6).  Conference sheets will be handed in class on Fridays, and we will work on the problems TOGETHER on the following Thursdays;  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

            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 260  FORMAT

            Hourly Exams.                                          450 Points (~46% 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 Problems (SSP) to do given in class, and taken from our textbook.  The four hourly exams will be administered during class time according to the schedule indicated below.

 

                                    Exam #1         FRIDAY, September 24, 2004

                                    Exam #2         WEDNESDAY, October 20, 2004

                                    Exam #3         FRIDAY, November 12, 2004

                                    Exam #4         MONDAY, December 6, 2004

 

            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.

 

MONDAY, DECEMBER 13, 2004:  3:00 5:00 PM

 

            Laboratory.                                               320 Points (~33% of Total Points)

            Laboratory sessions are discussed in more detail in a separate laboratory syllabus (CHE 260L).  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 seven (7) laboratory reports for a total of seven (7) laboratory experiments.

            The laboratory reports will count for 77% of the lab points.

            Post-laboratory Question Sheets.

            There will be nine (9) post-laboratory question sheets for a total of seven (7) laboratory experiments.

            The post-laboratory question sheets will count for 14% of the lab points.

            Laboratory Notebooks.

            Laboratory notebooks will be collected on the last week of class during laboratory session (week of December 6th), and you may receive up to a total of 9% of the lab points.  They will be returned to you during the first laboratory session of Spring 2005.

            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 192 Points in the present case (CHE 260);  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 + 320 = 970) = 873 Points of the 970 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 attempt to cover this semester in lecture.

Introduction

                  A. Line-Angle Drawings                                                                 5.9;  Handout

(or Line Structures, or Skeletal Structural Formulas)

            B. The Functional Groups                                                               p. 40;  Handout

 

Unit #1:          STRUCTURE & BONDING, PART I

            A. An Introduction to Structure and Bonding in                        1 (except 1.6)

Organic Compounds

            B. Covalent Bonding and Chemical Reactivity                           2

 

Unit #2:          AN INTRODUCTION TO ORGANIC CHEMICAL REACTIVITY

            A. Reactions of Organic Compounds as Acids                            3;  1.6;  16.1;  16.2;

and Bases                                                                                     16.3;  16.4

            B. Reaction Pathways                                                                                  4

 

Unit #3:          STRUCTURE & BONDING, PART II

            A. Alkanes and Cycloalkanes                                                                    5;  19.1;  19.4

            B. Stereochemistry                                                                           6

 

Unit # 4:         KEY REACTIONS AND MECHANISTIC THINKING

            A. Nucleophilic Substitution and Elimination                              7

Reactions

 

Unit #5:          FUNCTIONAL GROUPS AS A BASIS FOR STUDYING REACTIONS

                        AND SYNTHESIS

            A. Alkenes                                                                                         8;  25.6;  19.2;  19.3;

                                                                                                                        19.5

            B. Alkynes                                                                                         9

LABORATORY  OUTLINE

            The primary focus of CHE 260 lab (CHE 260L) is on the development of techniques that are important to the organic chemist, and the subsequent use of these techniques to prepare, purify, and analyze the products 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

August 30th                           HELLO!  Spectroscopy Lecture:  NMR  (Chap. 11)

September 6th                     Spectroscopy Lecture:  NMR  (Chap. 11)

September 13th                   Spectroscopy Lecture:  UV-Vis  (Chap. 12:  12.1)  &  IR  (Chap. 12:  12.2)

September 20th                   Spectroscopy Lecture:  IR  (Chap. 12:  12.2)  &  MS  (Chap. 12:  12.3)

September 27th                   CHECK-IN;  #1 Recrystallization & Melting Point Determination

October 4th                            #2/Part I MACROscale Fractional Distillation

October 11th                         #2/Part II Gas Chromatography (GC)

                                                      #3 Thin-Layer Chromatography (TLC)

October 18th                         #2/Part II Gas Chromatography (GC)

                                                      #3 Thin-Layer Chromatography (TLC)

October 25th                         #4 MICRO- and MACROscale Liquid-Liquid Extraction

November 1st                       #5/Part I Friedel-Crafts Acylation:  Acetylferrocene and

                                                      Diacetylferrocene

November 8th                      #5/Part II Separation by Column Chromatography of a 3 Component

                                                      Mixture

November 15th                   #6 Markovnikov Addition:  THP Ether Formation

November 22nd                   NO LAB Thanksgiving Recess

November 29th                   #7 Anti-Markovnikov Addition - Hydroboration/Oxidation

December 6th                       CHECK-OUT;  GOODBYE!  HAPPY HOLIDAYS!  SEE YOU NEXT YEAR!