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The definitive source of course information remains the original (paper) syllabus distributed in class.

Spring 2004 Chemistry 221Lycoming College

Click here for Chemistry 221 answer keys

Lycoming College                   Organic Chemistry II             Spring 2004

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 rxn mechanisms, substitution/elimination pathways, and IR interpretation.


Faculty  Dr. Chriss E. McDonald, (work phone 321-4186, home 433-4493, email mcdonald@lycoming.edu), no specific office hours but I'm usually around.  If I'm not at school you can probably catch me at home.  You may call me any time prior to 10 PM.


Course Format  

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


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


Assigned homework:  These will not be graded.  Homework will be discussed during the recitations.  Obviously the homework assignments will be a crucial study element for quizzes and tests.  Answer keys will be posted on the web.


Web-based supplements:  These sites are useful for lab writeup info (physical properties):  http://chemfinder.cambridgesoft.com/.  Heres a site which will be useful for our discussion of spectroscopy and structure determination: www.chem.ucla.edu/~webspectra/.  The UCLA site allows you to click on the solution to the problem.  Molecular data  useful for lab reports can be found at:  http://chemfinder.cambridgesoft.com/.  Of course, the Mahler-derived department website is also quite useful in terms of links:  www.lycoming.edu/chem/chemlink.htm Also, a chemical structure drawing program called Isis Draw can be downloaded for free: www.mdli.com

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 (220T), T 1:00 4:50 (220U),  R 7:45 11:35 (220X).  Be on time and come prepared!!!!!



Your grade will be based on the total number of points you obtain out of a possible 610.

Assignment of letter grades is based on the following scale:  A 610 -549 (100 - 90%), B 548 488 (89 - 80%), C 487 - 427 (79 - 70%), D 426 - 366 (69 - 60%), F 365 - 0 (59 - 0%).  The points will be distributed as follows:

quizzes               60 points

exams 1-3        300 points

final exam         100 points (cumulative ACS exam)*

laboratory         150 points

total                  610 points


*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 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).


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.  Im 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.  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.






Date     Topic                                                               Text                             Q/E

1/12     introduction/radicals                                          5.2,3,8

1/14     representative radical chains                              7.10, 10.3,4

1/16     mass spectrometry                                            12.1-3


1/19     NMR theory                                                     13.1-3,8,9

                                                                                    Chp 27, lab manual 

1/21     chemical shift and coupling                                13.10,11,13                 Quiz 1

1/23     proton NMR problems                         -


1/26     carbon NMR                                                    13.4,5

1/28     physical/spectroscopic properties of alcohols     17.1,2,12                    Quiz 2

1/30     substitution/elimination rxns of alcohols  17.3,7, 18.3


2/2       redox chemistry of alcohols                               17.8

2/4       Exam 1                                                 -                                   Exam 1

2/6       ethers                                                               18.1,4


2/9       epoxides                                                           18.7,8

2/11     diene structure                                                  1.6-9, 12, 14.2

2/13     electrophilic additions to dienes             14.3,4


2/16     the Diels-Alder rxn (finest in org. chem.)            14.5,6

2/18     intro to arenes                                                   15.1-3                          Quiz 3

2/20     Huckel's rule and arene spectroscopy                15.4-10




2/23     electrophilic aromatic substitution (EAS)            16.1-4

2/25     EAS on substituted arenes                                16.5-6                          Quiz 4

2/27     EAS on disubstituted arenes                              16.7


3/1                                                                               -

3/3       Spring Break Week                                          -

3/5                                                                               -


3/8       substituent modifications and multisteppers        16.10-12, 24.8

3/10     Exam 2                                                                                     Exam 2

3/12     aldehyde/ketone (A/K) intro, synth of A/K        19.1,2, 16



3/15     addition of H:-. R:- to A/K                                 19.3,4,5,8, 17.5,6

3/17     addition of protic nucleophiles to A/K   19.6,7, 9, 11

3/19     as above                                                           as above                 last day to drop


3/22     A/K synthetic and mechanistic problems            Chp. 19                       

3/24     the Wittig rxn                                                    19.12                           Quiz 5

3/26     carboxylic acids                                                20.1-3, 7,10


3/29     carboxylic acid derivatives                                21.1,10

3/31     nucleophilic acyl substitution (NAS)                  17.5,6, 21.2-7              Quiz 6

4/2       more NAS                                                       as above


4/5       addition of H:-. R:- to acid derivatives     as above

4/7       Exam 3                                                 -                                   Exam 3

4/9       no class                                                            -


4/12     keto-enol isomerism                              22.1

4/14     enol-based rxns                                                22.2-4

4/16     generation of enolates                                       22.5,6


4/19     alkylation of enolates (SN2)                               22.7,8

4/21     addition of A/K to enolates                               23.1-7

4/23     NAS of enolates                                               23.8-10


4/26     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.  Many of these 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 day.


WEEK DATES            TOPIC                                          ASSIGNED     WRITEUP DUE


1          1/13,15            Radical Polymerization of                      Chp. 41A         1/20,22

                                    Methyl Methacrylate, Check-in

2          1/20,22            The Reaction of  Carvone                     handout            2/3,5

                                    with HCl and Water (MS)                               

3          1/27,29            as above (NMR, IR)   

4          2/3,5                GC Analysis of an Isomeric                   Chp. 31, 19      2/10,12

                                    Mixture Generated by EAS

5          2/10,12            The Acylation of Anisole                       Chp. 30            2/24,26

6          2/17,19            as above (IR, NMR)                                       

7          2/24,26            The Diels-Alder Cycloaddition              Chp. 29            3/9,11

8          3/9,11              Qualitative Organic Analysis                  Chp. 33            3/30,4/1

9          3/16,18            as above

10        3/23,25            as above

11        3/30,4/1           The Synthesis of N-Methyl                   Chp. 43  or      part 1: 4/13,15

                                    Prozac or The

Synthesis of N,N-Diethyltoluamide:       handout,
                                    The Insect Repellent "Off"                     Chp. 40

12        4/6,8                as above                                                                       part 2: 4/20,22

13        4/13,15            as above

14        4/20,22            as above, check-out                                                                 ____


#A 15 point lab quiz will be on stoichiometry, sig figs, and IR spectral interpretation.  It will be given during the week 2 reflux period.


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