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.

For Chemistry 220 answer keys, click here.




Instructors:     Dr. Holly D. Bendorf  (lecture and lab)

                        Dr. Chriss McDonald (labs)

                        Daniel DiRocco (study group facilitator)


Office:             209 Heim Building


Phone:             Office: x 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:  Monday and Wednesday 10:15 to 11:05 am, by appointment or just stop 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" 6th 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.

• Safety glasses or goggles (sold by Chemistry Club).

• Calculator with logarithmic and exponential functions. 

Please note that programmable calculators may NOT be used during quizzes or exams.


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:                    Quizzes                                     105 points        

                                                Exams                                      300 points        

                                                Laboratory                                130 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, October 1; Friday, October 29; and Friday, December 3.  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 (on the next page) lists reading assignments for each class.  I suggest you skim the assignment before class and then read it again more thoroughly afterwards.  I highly recommend taking notes on the reading.  Detailed chapter outlines and problems for each reading assignment will be distributed throughout the semester.  Although the homework problems will not be collected, you should complete them before the next class period to insure that you understand the material.  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 individually or in groups, ask questions and review lecture material.


Extra Credit:  Extra credit points can be earned by attending departmental colloquia (3 per colloquium).  If you are unable to attend some or all of the colloquia, you may also earn colloquium bonus by writing a brief research paper on an organic chemistry-related topic (up to 10 points).  The instructor must approve the topic and will provide additional details regarding the requirements for the paper.  Extra credit papers will not be accepted after the final exam. Colloquium bonus is limited to 15 points.  Other bonus point opportunities may arise in class throughout the semester and are counted above and beyond the 15-point cap for colloquium bonus.



- Attendance is mandatory.  Students with perfect attendance will receive a 5 point bonus.  Students with three or more absences (regardless of the reason) will receive a 5 point deduction. 

- If you miss a quiz, you will receive a grade of zero on that quiz (remember, you get to drop one quiz).

- If you miss an exam, you will receive a grade of zero on that exam.  Exception:  If you cannot attend class that day due to exceptional circumstances (a routine doctor’s appointment is NOT an exceptional circumstance) and receive PRIOR approval from me, you may substitute your grade on the final for the missed exam.  You must be able to provide documentation regarding the reason for the absence.

- If you miss a lab, you will receive a grade of zero for that lab.  Lab make-ups may be permitted in some cases when the absence receives prior approval.  Labs must be made up during another regularly scheduled lab period.  Arriving late to lab will result in a deduction from the lab grade.


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. 

Acros Organics Catalog             www.acros.be              Aldrich Catalog             www.sigmaaldrich.com

Alfa Aesar                                www.alfa.com              Chemfinder       chemfinder.cambridgesoft.com


The Lycoming College Department of Chemistry            www.lycoming.edu/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 assignments, quizzes and exams will 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. 30

Intro. to Organic, Atomic Structure



Sept. 1

Lewis Structures, Bonding Theory

1.4-6, 12


Sept. 3

MO Theory, Hybridization







Week 2




Sept. 6

Polar Bonds, Formal Charges



Sept. 8

Drawing Structures, Functional Groups, Isomers

2.12-13; 3.1-3


Sept. 10

Alkanes and Cycloalkanes: Properties, Nomenclature







Week 3




Sept. 13

Conformations of alkanes



Sept. 15

Conformations of cycloalkanes



Sept. 17

Cyclohexane Conformers







Week 4




Sept. 20

Organic Reactions



Sept. 22

Polar Reactions, Arrow Notation



Sept. 24








Week 5




Sept. 27

Acid-Base Chemistry



Sept. 29

Kinetics and Thermodynamics Review



Oct. 1








Week 6




Oct. 4

Alkenes: Structure and Nomenclature



Oct. 6

Electrophilic Addition:  Reaction with HX



Oct. 8

Carbocation Reactivity and Rearrangements







Week 7




Oct. 11

Electrophilic Addition of X2 to Alkenes



Oct. 13

Electrophilic Addition of H2O to Alkenes

7.4-5, 9


Oct. 15

Long Weekend







Week 8




Oct. 18

Other Addition Reactions of Alkenes



Oct. 20

Alkynes:  Structure, Nomenclature, Properties



Oct. 22

Addition Reactions of Alkynes







Week 9




Oct. 25

Acid-Base Chemistry of Alkynes



Oct. 27

DU Calculations, IR Spectroscopy:  Theory

6.2; 12.5


Oct. 29








Week 10




Nov. 1

IR:  Functional Group Absorptions



Nov. 3

IR Practice



Nov. 5

Stereochemistry:  Chirality

9.1-4, 11






Week 11




Nov. 8

Assigning Absolute Configuration



Nov. 10

Enantiomers, Diastereomers & Meso Cmpds



Nov. 12

Consequences of Chirality, Alkyl Halides







Week 12




Nov. 15

SN2: Kinetics and Mechanism



Nov. 17

SN2: Leaving Group and Nucleophile



Nov. 19








Week 13




Nov. 22




Nov. 24

No Classes



Nov. 26

No Classes







Week 14




Nov. 29

E2: Kinetics and Mechanism



Dec. 1

E2: Stereochemistry, Bulky Bases



Dec. 3








Week 15




Dec. 6

Substitution and Elimination Summary



Dec. 8

Organic Synthesis



Dec. 10

Organic Synthesis







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 130 points and is comprised of nine lab write-ups (90 points total), three lab quizzes (30 points), and a lab technique evaluation (10 points).  The lab technique grade is assigned based on the following criteria:  preparation for lab, safety in the laboratory, ability to work efficiently in the laboratory, ability to successfully complete experiments, and laboratory hygiene.


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. 31, Sep. 2 Check-in                                        Chp. 1, 2, 3

    2             Sep. 7, 9           Distillation                                      Chp. 6, 7

    3             Sep. 14, 16        Recrystallization of Benzoic Acid    Chp. 4, 8-10            Distillation

                                           and Naphthalene

    4             Sep. 21, 23        Solubility Testing and Unknown       Chp. 8-10                Recryst. Part I


    5             Sep. 28, 30        Unknown Recrystallization              Chp. 3, 8-10, 14                                         

    6             Oct. 5, 7           Extraction                                      Chp. 11-13              Quiz 1

    7             Oct. 12, 14        Extraction                                      Chp. 11-13              Recryst. Part II      

    8             Oct. 19, 21        Dilantin, Part 1                               Chp. 16-18              Extraction

    9             Oct. 26, 28        Dilantin, Part 2                               Chp. 16-18              Dilantin Part I

    10            Nov. 2, 4           Limonene                                      Chp. 23-25              Quiz 2       

    11            Nov. 9, 11         E1, Limonene Characterization        Chp. 12, 19, 22        Dilantin Part II       

    12            Nov.  16, 18      E1 Characterization                                                      Limonene               

    13            Nov. 23, 25       Thanksgiving--No Labs                 

    14            Nov. 30, Dec. 2   E2                                               Chp. 16, 19, 26        E1             

    15            Dec. 7, 9           Check-out                                                                    E2    Quiz 3


*Late reports will be penalized 5% per school day.

Lab reports 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 31, 2004.
The URL for this page is http://www.lycoming.edu/chem/fall2004/220syl.htm