--------------------------------------------------------------

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.


Click here for Chemistry 221 homework keys.


Lycoming College  Organic Chemistry II  Spring 2000

http://www.lycoming.edu/dept/chem/spring2000/Image3.gif

Course Description  This course is designed to introduce the student to the chemistry of arenes, alcohols, 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 11 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):  www.sigma-aldrich.com, www.fisher1.com/catalogs/index.html .  Here’s 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.  Of course, the Mahler-derived department website is also quite useful in terms of links:   www.lycoming.edu/dept/chem/. Also, a chemical structure drawing program called Isis Draw 2.1.4 can be downloaded for free (!).  Go to the Yahoo website and search Isis Draw and you’ll be able to find it.

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!!!!!
 

Grading
Your grade will be based on the total number of points you obtain out of a possible 626.
Assignment of letter grades is based on the following scale:  A 626 -563 (100 - 90%), B 562 – 501 (89 - 80%), C 500 - 438 (79 - 70%), D 437 - 376 (60 - 69%), F 375 - 0 (59 - 0%).  The points will be distributed as follows:
 

Bio info

06 points

quizzes 

70 points

exams 1-3

300 points

final exam

100 points (cumulative ACS exam)*

laboratory

150 points

total 

626 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 15.   (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.  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.  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 

1.5, (lab manual Appendix F) 

all mechanistic discussions 

ubiquitous

curved arrow notation 

3.8, (lab manual Appendix F) 

all mechanistic discussions 

ubiquitous

formal, partial charges

1.6, 1.14 (Appendix F) 

all mechanistic discussions 

ubiquitous

E+ addition to alkenes 

Chp. 7 

E+ aromatic substitution 

Chp. 21

SN2/SN1 

Chp. 12 

alcohols/ethers/carbonyls 

Chps. 11,13-15

Infrared spectroscopy 

Chp. 5

 NMR spectroscopy 

Chps. 5, 10

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.
 
 

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 like to read apocalyptic fiction and I have a hamster named Ned Snodgrass McDonald (my son picked the name).
7. Tell me about your background in chemistry.  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

http://www.lycoming.edu/dept/chem/spring2000/Image4.gif

Please turn this in by 1/17/00.   Thanks.

CHEM 22100 CHRONODYNAMICS

Date 

Topic

Text   

Q/E

1/10 

Introduction/radicals     

18.1-4

 

1/12 

representative radical chain rxns   

18.5,6,8,9

 

1/14 

mass spectrometry     

18.14-16

 

1/17 

NMR theory      

5.8-14, lab manual Chp. 27

1/19 

sample NMR problems    

Chp. 10          

QUIZ 1 

1/21 

NMR subtleties     

Chp. 10

1/24 

carbon NMR       

Chp.10

1/26 

physical/spectroscopic properties of alcohols  

11.1-4            

QUIZ 2

1/28 

substitution/elimination rxns of alcohols  

11.15,17, 12.9, 13.8c

1/31 

redox chemistry and alcohols    

11.9, 11.18

2/2 

EXAM 1             

EXAM 1

2/4 

synthesis, reactions of ethers    

8.10, 13.8,13.10, 13.12

2/7 

diene structure      

19.4-7

2/09 

electrophilic addition to dienes   

19. 8,9

2/11 

the Diels-Alder rxn (finest in organic chem)  

19.12

2/14 

introduction to arenes     

20.1-3, 21.1

2/16 

Huckel’s rule and spectroscopy of arenes 

 20.4-8             

QUIZ 3

2/18 

electrophilic aromatic substitution (EAS)  

21.1-5

2/21 

more EAS      

21.6-10

2/23 

more EAS     

 21.6-10            

QUIZ 4

2/25 

EAS of substituted benzenes    

21.11-12

2/28 

SPRI

3/1    

              NG BR

3/3   

                            EAK

3/6 

substituent modifications and multistep sequences 

20.9,21.10, 22.10, 15,16

3/8 

EXAM 2                

EXAM 2

3/10 

aldehyde/ketone (A/K) intro, synth of A/K  

14.1-6

3/13 

addition of H:-, R:- to A/K    

11.7,8,10

3/15 

addition of protic Nu-H to A/K   

14.7-14

3/17 

as above      

14.7-14

3/20 

A/K synthetic and mechanistic problems  

Chp. 14

3/22 

 the Wittig rxn      

22.5-8          

QUIZ 5

3/24 

physical/spectroscopic properties of acids and esters 

15.1-4

3/27 

synthesis and acidity of acids    

15.5,6,8-10

3/29 

interconversion of acids and esters   

15.11,12,14         

QUIZ 6

3/31 

structure/spectroscopy of other carbonyl deriv. 

16.1-4

4/3 

NAS of other carbonyl derivatives   

16.5-9

4/5 

as above      

16.5-9          

QUIZ 7

4/7 

H:-, R:- addition to carboxylic acid derivatives  

16.12-14

4/10

NAS-based problems     

Chp. 15/16

4/12 

EXAM 3

EXAM 3

4/14 

keto-enol isomerism     

17.1,2,4

4/17 

alkylation of enolates    

 24.2-8

4/19 

aldol condensation     

17.5,6

4/21 

claisen condensation     

17.7

4/24-28 

final exam week

ORGANIC CHEMISTRY
LAB SCHEDULE SPRING 2000

 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 (not 3% as written in lab manual).
 

WEEK

DATES

TOPIC

ASSIGNED
READINGS

WRITEUP DUE

1

1/11,13 

Radical Polymerization of Methyl Methacrylate, Check-in

Chp. 41A 

1/18,20

2

1/18,20 

The Reaction of  Isoamyl Alcohol with Acetic Acid#

Chp. 39  

2/1,3

3

1/25,27 

as above (NMR, IR)

 

  

4

2/1,3 

GC Analysis of an Isomeric Mixture Generated by EAS

Chp. 31, 19 

2/8,10

5

2/8,10

The Nitration of Methyl Benzoate or 
Nitration of Acetanilide

Chp. 30
handout

2/22,24

6

2/15,17

as above (IR, NMR)

 

 

7

2/22,24

The Diels-Alder Cycloaddition   

Chp. 29 

3/9,11

8

3/7,9

Qualitative Organic Analysis   

Chp. 33

3/28,30

9

3/14,16

as above

 

 

10

3/21,23

as above

 

 

11

3/28,30

The Synthesis of Butyl-barbituric Acid or
Synthesis of an Ant Alarm Pheromone

Chp. 37  or
Chp. 40

part 1: 4/11,13

12

4/4,6

as above     

 

 part 2: 4/20,22

13

4/11,13

as above

 

 

14

4/20,22

as above, check-out

       

 

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


| Announcements & Schedules | Faculty & Staff | Curriculum & Courses | Research |
| Facilities & Equipment | Safety | Students & Alumni | Links | 3-D Molecules|

·  Back to the Chemistry Department Home Page!


The URL for this page is http://lyco2.lycoming.edu/dept/chem/spring2000/221syl.htm