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.

Fall 2002       Organic Chemistry I 220                Lycoming College




Instructor:            Dr. Holly D. Bendorf                                                                                                        

Office:                   209 Heim Building                                                                                   

Phone:                   office:  4365       home:  998-8647 (no later than 10 pm, please!)

e-mail:                   bendorf@lycoming.edu


Course Schedule:                Lecture:                  MWF  9:00 - 10:05,  Heim G-09

                                                Labs:                      T  7:45 - 11:35 am,  T 1:00 - 4:50 pm, R  7:45 - 11:35 am. 

                                                                                Prelab in Heim 220.  Lab in Heim 236.


Office Hours:  M &W 10:00 am - 11:00 am, R 1:00 pm - 2:00 pm, and by appointment, or just drop by.


Evening Review Session:  To be announced.


Course Description:  CHEM 220, Organic Chemistry I, is an introduction to the study of the chemistry of carbon compounds.  The course covers the chemistry of alkenes and alkynes, the substitution and elimination chemistry of alkyl halides, the theory and applications of  infrared spectroscopy, and the strategies of organic synthesis.  The laboratory portion of the course will introduce the student to a variety of techniques for the synthesis, purification, and analysis of organic compounds. 


Text and Materials:

• "Organic Chemistry" 5th Edition, John McMurry, Brooks Cole Publishers.

• "Study Guide and Solutions Manual for Organic Chemistry, John McMurry (optional).

• Molecular Model Set for Organic Chemistry (Lehman).  These can be shared.

• Bound laboratory notebook (Freeman).

• CHEM 220-221 lab manual (available in Chemistry office, room 212).

• Safety glasses or goggles.

• Lab deposit of $10, refundable upon check-out.

• Calculator with logarithmic and exponential functions.


Materials in Chemistry Reading Room:  Copies of several organic chemistry texts are available in the reading room (217  Heim Bldg.).  If you are not satisfied with McMurry’s treatment of a topic, feel free to consult one of the other textbooks--you may just find one you like.  These texts are excellent sources of extra practice problems (solutions manuals are available for several of the texts as well).


Grading Criteria:                                Intro Assignment                                     5 points             

Quizzes                                                  105 points             

                                                                Exams                                                     300 points             

                                                                Laboratory                                            125 points             

                                                                Final                                                       125 points             

                                                                                                                                660 points             


Final letter grades will be assigned as follows: >90% A, 80-90% B, 70-80% C, 60-70% D, <60% F.  The ranges given include "+" and "-" grades.  Be aware that you must pass both the lecture and laboratory to receive a passing grade for the course.


Exams:  There are three in-class exams on the following dates:  Friday, September 27;  Friday, October 25;  and Friday, November 22.  The final exam will be administered on the day and time assigned by the registrar.


Quizzes:  Quizzes are an incentive to stay current with the course.  They provide you with a means of evaluating your progress and allow you to identify any potential "trouble spots" before the exam.  The lowest quiz grade will be dropped.


Assignments From the Text:  The course outline (below) lists reading assignments for each class.  I suggest you skim the assignment before class and then read it more thoroughly afterwards.  I highly recommend taking notes on the reading.  Detailed chapter outlines and problems related to each reading assignment will be distributed throughout the semester.  Although the problems will not be collected, you should complete them before the next class period.  Lectures, quizzes, and in-class exercises are prepared with the expectation that you have read and understand the assigned material and have completed the problems.


Review Session:  The evening help session is an informal workshop where you will have the opportunity to work problems in groups, ask questions and review lecture material.


Extra Credit:  Extra credit points can be earned by attending departmental colloquia (3 per colloquium).  Extra credit points can also be earned by writing a brief research paper on a mutually agreed upon topic (up to 10 points).  Other types of extra credit projects may become available during the semester.  Extra credit is limited to 15 points.  Bonus points (i.e. from bonus questions on exams, etc.) do not count towards the 15 point max.


General Comments: 

Attendance:  Attendance is mandatory.  Three absences are permitted; additional absences will be penalized (3 points per absence).  Missed quizzes, exams and laboratory meetings can not be made-up unless the absence has prior approval from me and can be documented (for example, by a note from student health services or the Dean).  A missed quiz or exam will be recorded as a grade of zero.  Students who miss a mid-semester exam or quiz due to an excused absence (see above) will be given a single, cumulative make-up exam or quiz at the end of the semester. 


Study Suggestions:  Perhaps the best advice I can give you on how to succeed in this course is:  Don't get behind!  We cover a lot of material in this class and cramming for a night or two before an exam simply won't work.  Furthermore, each section builds upon the material covered in the previous chapters and to succeed in this course you need to be fluent with one chapter before moving on to the next.  Just like learning a foreign language or becoming proficient at a sport, you need to practice a bit each day.  Review your class notes, read the text, discuss the material with your classmates, quiz yourself, and most importantly:  work lots of problems.  And remember, my job is to help you learn organic chemistry--if you have questions, if you are not sure how to approach a certain type of problem, or if a concept is still a little fuzzy, ask me about it!


Useful resources on the web:

The on-line catalogs and databases are good sources of information for your lab reports.  We'll talk more about them at the first lab meeting.  On most of these sites, you can search for a chemical by its name (whole or partial) or by its formula.  Chemical listings normally include the name of the compound, common synonyms, formula, molecular weight, density, boiling point, melting point and a link to the MSDS (material safety data sheet) information.

                                                                Acros Organics Catalog                     www.acros.be      

                                                                Aldrich Catalog                                    www.sigmaaldrich.com/

                                                                Alfa Aesar                                             www.alfa.com

                                                                Chemfinder                                            chemfinder.cambridgesoft.com/


                                                                Yahoo                                                       www.yahoo.com/Science/Chemistry

There are numerous sites that list other chemistry-oriented web sites and Yahoo is one of them.  Yahoo lists web sites according to content (atmospheric chemistry, biochemistry, chemical and biological weapons, chemical constants, organic chemistry, periodic tables, etc.).  Yahoo also has MSDS information.


The Lycoming College Department of Chemistry           www.lycoming.edu/dept/chem/

Includes all sorts of Chemistry Department info:  syllabi, chemistry curriculum, faculty and student research, colloquium schedule, chem club activities, and links to other chemistry-related sites.  Answer keys for homework will also be posted in this site.



Course Outline:  The outline is tentative and subject to change.  Updated outlines will be provided throughout the semester!











Week 1




Aug. 26

Intro. to Organic, Atomic Structure



Aug. 28

Bonding Theory



Aug. 30

Lewis Structures, Hybridization







Week 2




Sept. 2

Polar Bonds, Formal Charges



Sept. 4

Drawing Structures, Functional Groups, Isomers

2.12-13; 3.1-3


Sept. 6

Alkanes and Cycloalkanes: Properties, Nomenclature







Week 3




Sept. 9

Conformations of alkanes



Sept. 11

Conformations of cycloalkanes



Sept. 13

Cyclohexane Conformers







Week 4




Sept. 16

Organic Reactions



Sept. 18

Polar Reactions, Arrow Notation



Sept. 20








Week 5




Sept. 23

Acid-Base Review



Sept. 25

Kinetics and Thermodynamics Review



Sept. 27








Week 6




Sept. 30

Alkene:  Structure and Nomenclature



Oct. 2

Electrophilic Addition:  Reaction with HX



Oct. 4

Carbocation Reactivity and Rearrangements







Week 7




Oct. 7

Electrophilic Addition of X2 to Alkenes



Oct. 9

Electrophilic Addition of H2O to Alkenes



Oct. 11

Other Addition Reactions of Alkenes







Week 8




Oct. 14

Alkynes:  Structure, Nomenclature, Properties



Oct. 16

Addition Reactions of Alkynes



Oct. 18

No Classes







Week 9




Oct. 21

Acid-Base Chemistry of Alkynes



Oct. 23

Organic Synthesis



Oct. 25




















Week 10




Oct. 28

DU Calculations, IR Spectroscopy:  Theory

6.2; 12.5


Oct. 30

IR:  Functional Group Absorptions



Nov. 1

IR Practice







Week 11




Nov. 4

Stereochemistry:  Chirality



Nov. 6

Assigning Absolute Configuration



Nov. 8

Enantiomers, Diastereomers and Meso Compounds







Week 12




Nov. 11

Consequences of Chirality, Alkyl Halides

9.13-19; 10.1-2


Nov. 13

SN2: Kinetics and Mechanism



Nov. 15

SN2: Leaving Group and Nucleophile







Week 13




Nov. 18




Nov. 20

E2: Kinetics and Mechanism



Nov. 22

Exam 3







Week 14




Nov. 25

E2: Stereochemistry, Bulky Bases



Nov. 27

No Classes



Nov. 29

No Classes







Week 15




Dec. 2




Dec. 4

Substitution and Elimination Summary



Dec. 6

Review and Catch-up!







Exam Week:



The final exam will be given on the date and time assigned by the registrar.  No exceptions!



Laboratory:  It is imperative that you come to the lab fully prepared.  Careful planning and preparation before you arrive at the lab will allow you to complete your experiments in an efficient and safe manner.  It is your responsibility to read and understand the lab procedure before you arrive at prelab.  Missing or arriving late to prelab will result in a reduced lab grade (up to 5 points per violation) and/or dismissal from the lab.

                The laboratory grade is worth a total of 125 points and is comprised of nine lab write-ups (90 points total), three lab quizzes (30 points), and a lab technique evaluation (5 points).    

                Lab Safety:  Unsafe behavior in the lab will not be tolerated and violations will be penalized.  Repeated violations during a class may result in a zero for that lab.  Keep in mind that lab safety includes laboratory hygiene.  In the event that common areas are left dirty, (rotovaps, balances, melting point apparati, reagent hood) points may be deducted from the entire lab section.  If you have any questions regarding lab safety, please do not hesitate to ask. 


Lab Outline:

Week                       Dates                Lab                                                                Assigned Reading            Report due for:*

      1                  Aug. 27, 29            Check-in                                                       Chp. 1

      2                  Sep. 3, 5                 Distillation                                                   Chp. 6, 7

      3                  Sep. 10, 12             Recrystallization of Benzoic Acid            Chp. 4, 8-10                   Distillation

                                                          and Naphthalene

      4                  Sep. 17, 19             Solubility Testing and Unknown             Chp. 8-10                       Recryst. Part I


      5                  Sep. 24, 26             Unknown Recrystallization                       Chp. 2-3, 8-10                                                            

      6                  Oct. 1, 3                  Extraction                                                     Chp. 11-13                     Recryst. Part II                                                                                                                                                                              Quiz 1

      7                  Oct. 8, 10                Extraction                                                     Chp. 14, 11-13                                                      

      8                  Oct. 15, 17              Dilantin, Part I                                             Chp. 16-18                     Extraction

      9                  Oct. 22, 24              Dilantin, Part 2                                            Chp. 16-18                                            

      10                Oct. 29, 31              Limonene                                                     Chp. 23-25                     Dilantin Part I

                                                                                                                                                                        Quiz 2           

      11                Nov. 5, 7                Limonene, E2                                               Chp. 12, 16, 26               Dilantin Part II             

      12                Nov. 12, 14            E2                                                                  Chp. 19                           Limonene                      

      13                Nov. 19, 21            E1                                                                  Chp. 19, 22                     E2 due in class: 11/25

      14                Nov. 26, 28            Thanksgiving--No Labs                                                                   

      15                Dec. 3, 5                 Limonene Characterization,                                                              E1

                                                               and Check-out                                                                               Quiz 3


*Late reports will be penalized 5% per school day will not be accepted after graded labs are returned. 

More info on lab safety, procedures and reports will be given at the first lab meeting.



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Last updated August 26, 2002.
The URL for this page is http://www.lycoming.edu/chem/fall2002/220syl.htm