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
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
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 |
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 |
Chp. 30 |
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 |
Chp. 37 or |
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.
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