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.

Lycoming College                   Organic Chemistry II             Spring 2007


Course Description  This course is designed to introduce the student to the chemistry of alcohols, arenes, and carbonyl compounds.  The approach will be both mechanistically and synthetically based.  The spectroscopic tools used to discern organic structure will also be examined in some detail.  The lab portion of the course will focus on synthetic organic chemistry, qualitative organic analysis, and mechanism.  We will be building on some key concepts from Chem 220, such as, Lewis structures, formal charges, basics of polar reaction mechanisms, substitution/elimination pathways, and IR interpretation.


Faculty  Dr. Chriss E. McDonald, (work phone 321-4186, home 998-8647, email mcdonald@lycoming.edu), no specific office hours but I'm usually around. 


Course Format  

Lectures:  MWF, 9:00-10:05, attendance will be taken daily. 


Recitations:  Problem solving sessions will be built into class time.  We will also have a weekly help session in the early evening.


Assigned homework:  There will be two assignments per topic.  One from the book and a homemade one that will be handed out at the help session.  These will not be graded but I expect you to do both.  Homework will be discussed during the help sessions.  Obviously the homework assignments will be a crucial study element for quizzes and tests.  Answer keys will be posted on the Moodle thingy.


Moodle-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 2005, and study guides


Other sites of value include:

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

www.chem.ucla.edu/~webspectra/                              (spectral interpretation),

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

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




Exams:  Exams 1-3 will be hour exams on the indicated days.  The final exam will be an American Chemical Society standardized, multiple choice-type deal (cumulative over the whole of organic chemistry).


Labs:  Similar to last semester.  Prelab still in HBC 220.  Note the times:  T  7:45 -11:35 (221M), T 1:00 – 4:50 (221N),  Th 7:45 – 11:35 (221Q).  Be on time and be prepared!!!!!



Your grade will be based on the total number of points you obtain out of a possible 620.

Assignment of letter grades is based on the following scale:  A 625 -562 (100 - 90%), B 561 – 500 (89 - 80%), C 499 - 437 (79 - 70%), D 436 - 375 (69 - 60%), F 374 - 0 (59 - 0%).  The points will be distributed as follows:

quizzes               70 points

exams 1-3        300 points

final exam         100 points (cumulative ACS exam)*

laboratory         150 points

total                  625 points


*a higher score on the final exam can be used to replace one 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 mind your manners you will receive 3 points per speaker.  You may also receive up to 8 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 two bibliographic sources).  The ceiling on bonus points is 12.   (excluding those on exams).


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.


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 (7 days/week) 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.  The good student will read the text, read the notes, review concepts from Chem 220 that are fuzzy (see below), make lists of questions to ask me, stay on top of things.  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 cumulative in the sense that we need to know the earlier material to comprehend the latter.  Speaking of the cumulative nature of organic chemistry, here is a list of Chem 220 topics that significantly impact our studies in Chem 221.  I strongly suggest these topics be reviewed prior to studying the relevant new material.


220 Topic                    Text location                 221 Topic                    Text location

Lewis structures                     lab manual Appendix F           all mechanistic discussions    ubiquitous

functional groups                    Chp 3                                      all synthetic discussions        ubiquitous

curved arrow notation             5.4,5, Appendix F                    all mechanistic discussions    ubiquitous

formal, partial charges             2.1, Appendix F                       all mechanistic discussions    ubiquitous

E+ addition to alkenes             6.8-10                                      E+ aromatic substitution        Chp. 16

SN2/SN1                                   Chp. 11                                   alcohols/ethers/carbonyls       Chps. 17,18

infrared spectroscopy             Chp. 12                                   NMR spectroscopy                              Chp. 13


Attendance policy

Attendance at quizzes and exams is mandatory.  Makeups will be administered only if I deem the reason for the 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.





Week  Date      Topic                                                               Text                             Q/E

            1/8       introduction/radicals                                          5.2,3,8

1          1/10     representative radical chains                              7.10, 10.3,4

            1/12     mass spectrometry                                            12.1-3


            1/15     NMR theory                                                     13.1-3,8,9, Chp 27, lab manual

2          1/17     chemical shift and coupling                                13.10,11,13                

            1/19     proton NMR problems                         -                                   Quiz 1


            1/22     carbon NMR                                                    13.4,5

3          1/24     physical/spectroscopic properties of alcohols     17.1,2,12                    

            1/26     substitution/elimination rxns of alcohols  17.3,7, 18.3                 Quiz 2


            1/29     redox chemistry of alcohols                               17.8

4          1/31     ethers                                                               18.1,4             

            2/2       Exam 1                                                 -                                  Exam 1




            2/5       epoxides                                                           18.7,8

5          2/7       diene structure                                                  1.6-9, 12, 14.2

            2/9       electrophilic additions to dienes             14.3,4


            2/12     the Diels-Alder rxn (finest in org. chem.)            14.5,6

6          2/14     intro to arenes                                                   15.1-3                                     

            2/16     Huckel's rule and arene spectroscopy                15.4-10                        Quiz 3


            2/19     electrophilic aromatic substitution (EAS)            16.1-4

7          2/21     EAS on substituted arenes                                16.5-6                         

            2/23     EAS on disubstituted arenes                              16.7                             Quiz 4


            2/26                                                                             -

            2/28     “Spring” Break Week                                       -

            3/2                                                                               -


            3/5       substituent modifications and multisteppers        16.10-12, 24.8

8          3/7       aldehyde/ketone (A/K) intro, synth of A/K        19.1,2, 16                   

            3/09     Exam 2                                                 -                                   Exam 2


            3/12     addition of H:-, R:- to A/K                                 19.3,4,5,8, 17.5,6

9          3/14     addition of protic nucleophiles to A/K   19.6,7, 9, 11

            3/16     as above                                                           as above


            3/19     A/K synthetic and mechanistic problems            Chp. 19                       

10        3/21     the Wittig rxn                                                    19.12                                       3/23     carboxylic acids                                                20.1-3, 7,10                 Quiz 5 


            3/26     carboxylic acid derivatives                                21.1,10           

11        3/28     nucleophilic acyl substitution (NAS)                  17.5,6, 21.2-7                          3/30     more NAS                                                       as above                       Quiz 6


            4/2       addition of H:-. R:- to acid derivatives     as above          

12        4/4       Exam 3                                                 -                                  Exam 3

            4/6       Good Friday – no class                         -


            4/9       keto-enol isomerism                                          22.1

13        4/11     enol-based rxns                                                22.2-4

            4/13     generation of enolates                                       22.5,6


            4/16     alkylation of enolates (SN2)                               22.7,8

14        4/18     addition of A/K to enolates                               23.1-7                          Quiz 7

            4/20     NAS of enolates, conjugate addition                 23.8-10


            4/23 -   final exams






            The lab component of this course is worth 150 points.  Except for the three week Qualitative Organic Analysis lab, all of the lab writeups will be worth 15 points each.#  The QOA lab will be worth a whopping 30 points.  The week 2 quiz on IR, stoichiometry, and significant figures will be worth 15 points.  Many of the experiments will be inquiry-based and will impact what we do in lecture as well.  Students who do not conform to my notions of laboratory etiquette (as described in Chp. 1 of the lab manual) will be penalized.  You will be expected to be on time, to read the experiment ahead of time, to perform the experiment in a safe manner, to keep your personal area and the common areas of the lab clean, and to be courteous to your labmates.   The penalty for late lab reports is 5% per school dayLab reports cannot be turned in after any have been returned.


WEEK DATES              TOPIC                                         ASSIGNED       WRITEUP

                                                                                           READINGS          DUE*

1          1/9,11              Radical Polymerization of                      Chp. 46A         1/23,25

                                    Methyl Methacrylate, Check-in

2          1/16,18            The Attack of the Killer Protons            Chp. 30            1/30,2/1

                                    On Carvone#               

3          1/23,25            as above          

4          1/30,2/1           Diels-Alder Cycloaddition                     Chp. 33            2/13,15

                                    Of Cyclopentadiene with

                                    Maleic Anhydride                                

5          2/6,8                GC Analysis of an Isomeric                   Chp. 37            2/20,22

                                    Mixture Generated by E.A.S.

6          2/13,15            The Nitration of Methyl Benzoate          Chp. 35            3/6,8               

7          2/20,22            as above

                                    Spring Break

8          3/6,8                Qualitative Organic Analysis                  Chp. 38            3/27, 29

9          3/13,15            as above

10        3/20,22            as above

11        3/27,29            The Synthesis of N-Methyl                   Chp. 44           

                                    Prozac or                                             or                     part 1: 4/10,12

The Synthesis of Virstatin                      Chp. 45           
12        4/3,5                as above                                                                                              

13        4/10,12            as above                                                                       part 2:  final  exam

14        4/17,19            as above, check-out                                                                 ____


#The 15 point lab quiz will be during the week 2 reflux period.

*Writeups (STAPLED) will be due at the beginning of prelab on the indicated day.

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