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 Homework keys and other class materials please click here

Fall 2005       Chemistry 220              Lycoming College

Fall 2005               Organic Chemistry 1              Lycoming College

Course description - This course is designed to introduce the student to the chemistry of alkanes, alkenes, alkynes, and alkyl halides.  The approach will be both mechanistically and synthetically oriented.  The laboratory component of this course will involve the basic techniques of synthetic organic chemistry.


Faculty                                           Responsibilities                                                      Office

Dr. Chriss McDonald*                    lectures, lab, recitations                                         HBC 233

Dr. Holly Bendorf                           Lab                                                                        HBC 209


*321-4186 or e-mail (mcdonald@lycoming.edu)


Texts etc.

a.     Organic Chemistry,6th ed by McMurry#

b.     Chemistry 220 Lab Manual, by McDonald, Bendorf, and Berkheimer

c.     Bound laboratory notebook by Freeman#

d.     Lab safety glasses (sold by Chem Club)

e.     Calculator (add, subtract, multiply, divide, logs)#

f.      Lab deposit, $10 at lab check-in, cash only (refundable upon checkout)

#available at the bookstore


Course format

Lectures - MWF, 9:00 – 10:05, HBC G09, Attendance required.


Recitations – Problem solving sessions will be built into class time.  We will also have a weekly help session in the evening (starting week 2).


Assigned homework - Problems designed to enhance your understanding and prepare you for testing situations.  A key will be posted on the web.  Homework will not be collected. 


Laboratory - M: 7:45 – 11:35 pm; Tuesday,  N:  1:00 – 4:50 pm, Tuesday; Q: 7:45 – 11:35 pm, Thursday,  HBC 220, 234.  Attendance required.  Here you will experience what chemists actually do.  Your labwork will be evaluated as described in the lab syllabus as well as on the lecture exams.  Approximately 5% of each exam will be drawn from the labwork.  A lab syllabus will be distributed at the first lab session.  Make sure and show up with your $10 lab deposit (cash only) that first week.  Meet at 9:30 for morning lab sections this first week.

Grading scheme

a.        The final grade is based on the number of points obtained out of a possible 600 points.  The points will be                distributed as follows:

Biographical info                                                                  5 points (1%)

        quizzes                                                                              70 points (11%)

        exam 1                                                                            100 points (16%)

        exam 2                                                                            100 points (16%)

        exam 3                                                                            100 points (16%)

        final exam (cumulative)*                                                  120 points (20%)

        laboratory                                                                        120 points (20%)

        total                                                                                                615 points (100%)


*a higher score on the final exam can be used to replace a lower score from exam 1-3.

As always you will have the opportunity to obtain bonus points through attendance at our colloquium series.  Assuming you stay for the whole show and follow the guidelines below you will receive 3 points per colloquium.  You may also receive up to 6 bonus points by writing a paper on a topic that we have mutually agreed upon (2-3 pages, typewritten, double spaced, with a minimum of 2 bibliographic sources.  The ceiling on bonus points (excluding bio assignment and those on exams) is 12.


Guidelines for Attending Colloquium:

i.      Be on time

ii.      The speaker has expended a lot of effort to prepare for the talk.  Be attentive and polite.

iii.     If you can’t stay for 45 minutes for an internal speaker or 60 minutes for an external speaker, don’t come (please do not ask the speaker how long the talk will last).

iv.     Realize that questions for the speaker at the end is part of the talk and you will be expected to stay for that as well.


b.     Assignment of letter grades is based on the following scale:  553 - 615 A, 492 - 552 B, 431 - 491 C, 369 - 491 D, < 368 F.


c.     A word about learning chemistry.  Studying chemistry is hard work for most people (this is certainly true for me).  I would recommend that you work on the lecture               material at least one hour per day outside of class for starters.  Once you see how things are going this amount can be adjusted as needed (I suggest a significant increase in study time prior to an exam).  If you are having trouble, make sure and come and see me.  I’m easy to talk to and will do whatever I can to help you.  You will be responsible for all of the material listed on the following schedule for the indicated exams and quizzes.  It is not sufficient to learn the material from the lecture alone.  You are expected to read and think about the material prior to the lecture.  We must necessarily cover a large amount of material so our pace must be geared towards those who are ready to learn.  The hour exams will be somewhat cumulative in the sense that we need to know the earlier material to comprehend the latter.


d.        Web-based supplements:  There is a website for this course which includes homework keys (primarily from the text), extra problems keys (homemade problems), sample exams from the last time I taught this course, and study guides at:



Other sites of value include:

chemfinder.cambridgesoft.com (useful for lab writeup info),

www.lycoming.edu/chem/chemlink.htm (useful links from the departmental webpage)

www.mdli.com (a FREE chemical drawing program!!)

www.shef.ac.uk/chemistry/orbitron (more info about orbitals and bonding)


Policy on attendance

Attendance at quizzes and exams is mandatory.  Makeups will be administered only if I deem the reason for absence to be legitimate and I am made aware of the absence beforehand.  Each documented, unexcused lecture absence beyond the first two will cost you one point from your total.       















Lycoming College               Organic Chemistry 1           Fall 2005




“Organic Chemistry nowadays almost drives me mad.  To me it appears like a primeval tropical forest full of the most remarkable things, a dreadful endless jungle into which one does not dare enter, for there seems no way out.”


                                                                                Freidrich Wohler, 1835

                                                                (the slayer of the vital force theory)




week date               topic       (tetragob)                                                                              text                   quiz/exam


         8/29                hello organic chemistry!                                                                           Preface, 1 (p. 1-3)                  

1       8/31                ionic, covalent bonds,Lewis structures                                                     1.1, 4,5

           9/2                formal charge, resonance, functional groups                                          2.1-4,12,13, 3.1


           9/5                introductory molecular orbital theory                                                       1.2,3,6,7

2         9/7                orbital hybridization                                                                                  1.8-12                     

           9/9                as above                                                                                                  1.8-12                      QUIZ 1


         9/12                naming/drawing alkanes                                                                          3.2-4

3       9/14                alkane properties, cycloakanes                                                                3.5-8

         9/16                alkane conformational issues                                                                   4.1-3                        QUIZ 2


         9/19                ring strain, cycloalkane conformers                                                         4.4-13

4       9/21                acid-base reactions                                                                                 2.4-10, 24.4

         9/23                EXAM 1                                                                                                   -                               EXAM 1


         9/26                curved arrow formalism in acid-base rxns                                               2.11                        

5       9/28                classification of organic reactions                                                             5.1-5                       

         9/30                polar reaction examples                                                                          5.6


         10/3                basic thermodynamics/kinetics                                                 5.7-10

6       10/5                structure/nomenclature of alkenes                                                          6.1,3-5,7                 

         10/7                addition of HX to alkenes                                                         -               6.8-10                      QUIZ 3


       10/10                as above + cation rearrangements                                                          6.11,12

7     10/12                addition of X2, halohydrin formation                                                         7.2-3                       

       10/14                oxymercuration, hydroboration                                                                7.4,5                        QUIZ 4


       10/17                other alkene rxns                                                                                     7.7,8

8     10/19                alkyne nomenclature/structure additions to alkynes                 8.1,2                        QUIZ 5   

       10/21                long weekend                                                                                          -




       10/24                alkyne HX, X2 additions                                                                           8.4          

9     10/26                alkyne hydrations, reductions                                                                  8.5,6

       10/28                EXAM 2 (100 points)                                                                               -                               EXAM 2


       10/31                enantiomerism (last day to drop)                                                             9.1-3

10     11/2                optical activity                                                                                           9.3,4                       

         11/4                sequence rule                                                                                          9.5,6.6


         11/7                diastereomers                                                                                         9.6-11

11     11/9                stereochemical analysis of selected rxns                                 9.12-14                                   

       11/11                infrared spectroscopy:  theory                                                 12.5,6                      QUIZ 6


       11/14                infrared spectroscopy:  interpretation                                                      24, Lab Manual      

12   11/16                infrared spectroscopy:  interpretation                                                      6.2, 12.7-9

       11/18                kinetics/ stereochemistry of substitution                                                   11.1-3                      QUIZ 7


       11/21                the SN2 rxn                                                                                              11.4,5     

13   11/23                Tgiving

       11/25                Tgiving


       11/28                the SN1 rxn                                                                                              11.6-9

14   11/30                the E2 rxn                                                                                                11.10-12

         12/2                EXAM 3                                                                                                   -                               EXAM 3


         12/5                the E1 rxn, summary of substitution and elimination                                11.14,15 

15     12/7                alkylation of alkyne conjugate bases                                                        8.8,9, 11.16

       12/10                multistep syntheses, pheromones                                                           8.10


       12/13                Final Exam Week  (120 points)







WEEK          DATES        TOPIC                                                                                             WRITEUP DUE                                       ASSIGNED              QUIZ

                                                                                                                                                FOR WEEK #                                          READINGS


1                  8/30,9/1       Intro, check-in                                                                                                  -                                               Chp. 1-3

2                  9/6,8            Simple and Fractional Distillation                                                                     -                                               Chp. 6, 7

3                  9/113,15      Recrystallization (Part 1,2)                                                                              2 (Distillation)                           Chp. 8-10

4                  9/20,22        Recrystallization (Part 3)                                                                                 3 (Recrystallization 1)              Chp. 8-10,4

5                  9/27,29        Recrystallization (Part 4)                                                                                 -                                               Chp. 8-10,4             QUIZ 1

6                  10/4,6          Synthesis of Isobutyl Propanoate                                                                    4,5 (Recrystallization 2)           Chp. 44,12,14,16

7                  10/11,13      Extraction (Part 1)                                                                                           6 (Isobutyl Propanoate)           Chp. 11,13

8                  10/18,20      Extraction (rest of Part 1,2)                                                                             -                                               Chp. 11,13

9                  10/25,27      Synthesis of Benzil                                                                                           7,8 (Extraction)                        Chp.  17,18

10                11/1,3          Synthesis of Dilantin                                                                                        -                                               Chp. 18                   QUIZ 2

11                11,8,10        Limonene (Part 1)                                                                                           9 (Benzil)                                 Chp. 23,25                     

12                11/15,17      Limonene (Part 2)                                                                                           10 (Dilantin)                             Chp. 23-25

13                11/22,24      no lab                                                                                                              -                                               -

14                11/29,12/1   E2 (rxn, workup)                                                                                             11,12 (Limonene)                    Chp. 26

15                12/6,8          E2 (GC), clean hood/bench, checkout                                                             -                                               Chp. 26, 19             QUIZ 3

                     Finals week                                                                                                                        14,15 (E2)

GRADING:  The lab component of  your grade is 120  points out of the 610 for the course.  There will be 9  grades for writeups, 10  points each, for 90 points.  A typical grade for a writeup  can be broken down into three parts:  content of the writeup (60%), yield of the product (20%), purity of the product (20%).  Late lab writeups will cost you 5%  per school day.  Lab writeups cannot be turned in after the graded labs have been returned.  There will also be three 10 point lab quizzes.  Students who do not conform to our notions of laboratory etiquette (Chp. 1, p. 2  in the lab manual) can expect to have points deducted from their lab score.  This can be done either within individual writeups for isolated incidents or as a deduction from the total score for semester-long offenses.  In cases where common areas of the lab (balances, melting point apparatus.....) are abused or left messy, an entire lab section may have points deducted.


USEFUL SUPPLEMENTARY SOURCES:  One part of your lab writeup requires you to list several physical properties for the compounds involved in that particular experiment.  This information can be obtained most conveniently from one of the following:

1)     The Merck Index - located in the lab, the reading room, and the library reference collection (RS.51);

2)     The CRC Handbook of Chemistry and Physics - located in the lab, the reading room, and the library  reference collection (QD.65);

3)       The Aldrich Catalog - located in the lab and the reading room;

4)     Lange’s Handbook of Chemistry - located in the reading room;

5)     www.chemfinder.camsoft.com















Tell me about yourself …………… Please include the following info for full credit –

1. Name and what you like to be called;  Chriss McDonald, you may call me Chriss, Dr. McD, or Dr. McDonald.

2. Major (and note whether it is intended or actually declared); As an undergrad (late 70’s) I was actually a medical

technology major.

3. Minor (and note whether it is intended or actually declared); An unofficial one in history.

4. Fr.,  So.,  Jr.,  Sr.; Very senior.

5. 4 digit code for the posting of grades; N/A.

6. Tell me two interesting/funny things about yourself;  I play too many sports and my body is falling apart. Went to Gettysburg this summer and walked the ground over which Pickett’s charge occurred.

7. Tell me about your background in chemistry.  I thought chemistry was merely OK until I got to organic, went bonkers over that.  Went to grad school at Miami of Ohio in synthetic organic chemistry.  Still learning lots of cool stuff about

organic chemistry.  I’m interested primarily in the development of new synthetic methods.  Specifically the

development of new strategies for carbon – carbon bond formation.

8. A recent photo of yourself (2 point bonus);  see below




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Last updated August 30, 2005.
The URL for this page is http://www.lycoming.edu/chem/fall2005/220syl.htm