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 homework and problem set keys and other class materials
CHEMISTRY 221
SPRING 2002 SYLLABUS
Instructors:
Dr. Holly D. Bendorf Office: 209 HBC Phone: x4365 (office), 998-8647 (home)
Chris Robbins Study Group Facilitator Phone: x4428
Course Schedule:
Lecture: MWF 9:00 - 10:05
Labs: T
7:45 - 11:35 am, T 1:00 -
4:50, and R 7:45 - 11:35 am.
Office Hours: M 10:15 – 11:30, W 1:00 – 2:00, R 1:00 –
2:00 or just drop by.
Evening Review Session: Time and location TBA.
Course Description: CHEM 221, Organic Chemistry II, is a
continuation of CHEM 220. CHEM 221 will
focus on the reactions of organic compounds and their mechanisms, the
application of these reactions to organic synthesis, and the identification of
organic compounds using modern spectrometric techniques.
Text and Materials:
• "Organic Chemistry," 5th ed., by John McMurray.
•
Bound laboratory notebook (Freeman).
•
CHEM 220-221 lab manual.
•
Safety glasses or goggles (available at College Store).
•
Calculator with logarithmic and exponential functions.
Other Useful Materials: Copies of several organic chemistry texts are
available in the reading room. If you
are not satisfied with McMurray's treatment of a topic in his text, feel free
to consult one of the other textbooks--you may just find one you like. Also, these texts are excellent sources of
extra practice problems. A useful web
site for NMR practice can be found at www.chem.ucla.edu/~webspectra/.
Grading Criteria: Quizzes (6) 90 points
Exams
(3) 300
points
Laboratory 110 points
Final 100 points
600
points
Final
letter grades will be assigned as follows:
540-600 A, 480-540 B, 420-480 C, 360-420 D.
Exams:
There will be three in-class exams on the following dates: Friday,
February 8;
Quizzes: Quizzes are an incentive to stay current with
the course. They provide you with a
means of evaluating your progress and allow you to identify any potential
"trouble spots" before you get into an exam. The lowest quiz grade will be dropped.
Assignments From
the Text: Readings and problems from
the text will be assigned throughout the semester. It is your responsibility to stay current
with these assignments. Although they
will not be collected, it is strongly suggested that you complete the
assignments and have any questions answered before the next class period. Lectures, quizzes, and in-class assignments
are prepared with the assumption that you have read and understand the assigned
material and have completed the text problems.
Some quiz and exam problems may be taken directly from the text. Answer keys will be posted on the Chemistry
Department web site (exact URL TBA!)
Review Session: The evening review session is an informal
workshop where you will have the opportunity to ask questions, review the
course material, and work problems either individually or in groups.
Extra Credit: Extra credit points (3) can be earned by attending departmental colloquia. Extra credit points can also be earned by writing a brief research paper on a mutually agreed upon topic (up to 8 points, see me for more details). Other types of extra credit projects may become available during the semester. Extra credit is limited to 15 points.
General Comments:
Attendance: Regular attendance at lecture is
expected. Attendance at quizzes, exams and laboratory meetings is mandatory. You will be permitted to make-up a missed lab
or exam only when the absence has received prior approval from me (usually a case of medical or family
emergency which can be documented). You
must be able to attend another lab section in order to make-up a missed
lab. In the case of a missed exam, the
grade earned on the final exam will be substituted for the missing exam
grade. Quizzes cannot be made-up. Feel free to contact me at home: 998-8647.
Participation: Participation in class is expected. Please let me know if I am going too quickly
or have not explained something to your satisfaction. I try to encourage an informal, relaxed
environment -- I want everyone to feel comfortable asking questions and
discussing problems.
Study
Suggestions: The material covered in
CHEM 221 builds upon the concepts covered in CHEM 220. Lectures, in-class assignments, and labs have
been prepared with the assumption that everyone has a solid grounding in the
material from CHEM 220. You are therefore
responsible for the CHEM 220 material and should review when necessary. If you have any questions or would like some
assistance in reviewing, please ask!
As
you already know from CHEM 220, organic chemistry does not lend itself to
memorization or last-minute cramming.
This is true to an even greater extent in CHEM 221. The best approach for studying organic is to
practice everyday: review your notes, study
the text, discuss the material with your friends, quiz yourself, and
most importantly, work lots of problems!
Finally, if you feel that you are having trouble in the course, come see me right away. I am always willing and (almost!) always available to help you.
Course Outline: The outline is tentative and subject to
change.
|
Week |
Date |
Topics |
Class
Preparation |
Q/E |
|
Read
the following sections in the text: |
||||
|
1 |
Jan.
7 |
Radicals,
Rad. Halogenation |
Chapter
5.2-3 |
|
|
Jan.
9 |
Rad.
Hal.; Rad. Add'n to alkenes |
10.1-4 |
||
|
Jan.
11 |
Polymerization,
mass spectroscopy |
7.10;
12.1-4 |
||
|
2 |
Jan.
14 |
NMR-Theory,
recognizing symmetry |
13.1-3 |
|
|
Jan.
16 |
13C
NMR |
13.4-7 |
||
|
Jan.
18 |
1H
NMR - chemical shift |
13.8-10 |
Quiz
1 |
|
|
3 |
Jan.
21 |
1H
NMR - spin-spin splitting |
13.11-13 |
|
|
Jan.
23 |
NMR
wrap-up and problems |
|||
|
Jan.
25 |
Resonance
Review |
handout |
Quiz
2 |
|
|
4 |
Jan.
28 |
Diene structure and properties |
14.1-4,
10-13 |
|
|
Jan.
30 |
Reactions
of dienes with electrophiles |
14.5-7 |
||
|
Feb.
1 |
Diels-Alder
reaction |
14.8-9 |
Quiz
3 |
|
|
5 |
Feb.
4 |
Benzene:
prop's, structure |
15.1-4 |
|
|
Feb.
6 |
Aromaticity |
15.5-10 |
||
|
Feb.
8 |
EXAM
1 |
Exam
1 |
||
|
6 |
Feb.
11 |
Electrophilic Aromatic Substitution |
16.1-4 |
|
|
Feb.
13 |
More
EAS |
16.5-6 |
||
|
Feb.
15 |
EAS
of subst. benzenes |
16.6-7 |
||
|
7 |
Feb.
18 |
oxid'n and red'n of aromatic compounds |
16.10-11 |
|
|
Feb.
20 |
Multistep
synthesis of benzene cmpds |
16.12,
pp 645-653 |
||
|
Feb.
22 |
Alcohols:
prop., struct., acid-base chem. |
17.1-3,
12 |
Quiz
4 |
|
|
Feb.
25 |
Spring |
|||
|
Feb.
27 |
Break |
|||
|
Mar.
1 |
No Classes |
|||
|
8 |
Mar.
4 |
Reactions
of ROH |
10.7;
17.4, 7-9 |
|
|
Mar.
6 |
Ethers |
18.1-5 |
||
|
Mar.
8 |
Epoxides |
18.7-10 |
Quiz
5 |
|
|
9 |
Mar.
11 |
Aldehydes & Ketones: properties |
pp
743-752; 19.1-3, 16 |
|
|
Mar.
13 |
Prep'n of ald. and ket.,
Reactions |
19.4-7,
17.5 |
||
|
Mar.
15 |
EXAM
2 |
Exam
2 |
||
|
10 |
Mar.
18 |
Reactions
of A/K with nucleophiles |
19.8,
17.6, 10.8-9 |
|
|
Mar.
20 |
Reactions
of A/K with nucleophiles |
19.6,
9, 11 |
||
|
Mar.
22 |
More
reactions of ald. and ket. |
19.12. |
||
|
11 |
Mar.
25 |
Acids
and Esters: struct and props. |
20.1-5,
9 |
|
|
Mar.
27 |
Prep'n of acids and esters |
20.6-7 |
Quiz
6 |
|
|
Mar.
29 |
No
Classes-Good Friday |
|||
|
12 |
Apr.
1 |
Rxns. of acids and esters |
20.8,
21.6 |
|
|
Apr.
3 |
Acid
derivs: structure and reactivity |
21.1-3 |
Quiz
7 |
|
|
Apr.
5 |
Interconversion of acid derivs-NAS |
21.4-5 |
||
|
13 |
Apr.
8 |
Nucleophilic Acyl Substitution |
21.6-7 |
|
|
Apr.
10 |
More
Nucleophilic Acyl
Substitution |
21.8,
11 |
||
|
Apr.
12 |
EXAM
3 |
Exam
3 |
||
|
14 |
Apr.
15 |
Keto-Enol Tautomerization |
22.1-3 |
|
|
Apr.
17 |
Enolate chemistry |
22.5-8 |
||
|
Apr.
19 |
Aldol, Claisen chemistry |
23.1-4,
6-8 |
||
Laboratory: It is imperative that you come to the lab
fully prepared. Careful planning and
preparation before you arrive at the lab will allow you to complete your
experiments in an efficient and safe manner.
It is your responsibility to read and understand the lab procedure
before you arrive at prelab. Missing or arriving late to prelab will result in a reduced lab grade (up to 5 points
per violation) or dismissal from the lab, in which case you will receive a zero
for that lab.
The laboratory grade is worth a total of 110 points and consists of 8 lab reports and one 15-point lab quiz. Late reports will be penalized 5% per school day.
Lab Safety: Unsafe behavior in the lab will not be tolerated and violations will be penalized. Repeated violations during a class may result in a zero for that lab. Keep in mind that lab safety includes laboratory hygiene. In the event that common areas are left dirty, (rotovaps, balances, melting point apparati, reagent hood) points may be deducted from the entire lab section. If you have any questions regarding lab safety, please do not hesitate to ask.
Lab Syllabus
|
Week |
Dates |
Lab |
Required
Reading |
Week
Due |
Lab
Point |
|
Value |
|||||
|
1 |
Jan.
8, 10 |
Check-In,
Rad. Polym. |
Chap.
41A |
3 |
10 |
|
2 |
Jan.
15, 17 |
BF3
Reaction, lab quiz* |
Chap.
28, 11, 12, 17 |
4 |
10 |
|
3 |
Jan.
22, 24 |
as
above (NMR, IR) |
Chap.
24, 27 |
||
|
4 |
Jan.
29, 31 |
Diels-Alder
Cycloaddition |
Chap.
29 |
6 |
10 |
|
5 |
Feb.
5, 7 |
EAS |
Chap.
31, 19 |
7 |
10 |
|
6 |
Feb.
12, 14 |
Acylation of Anisole |
Chap.
45 |
8 |
10 |
|
7 |
Feb.
19, 21 |
as
above (NMR, IR) |
Chap.
24, 27 |
||
|
Feb.
26, 28 |
Spring
Break |
||||
|
8 |
Mar.
5, 7 |
Q.O.A. |
Chap.
33 |
12 |
25 |
|
9 |
Mar.
12, 14 |
Q.O.A. |
|||
|
10 |
Mar.
19, 21 |
Q.O.A. |
|||
|
11 |
Mar.
26, 28 |
Synthesis
Project |
Chap
40 or 43 |
part
1: 13 |
10 |
|
12 |
Apr.
2, 4 |
as
above |
part
2: 14 |
10 |
|
|
13 |
Apr.
9, 11 |
as
above |
|||
|
14 |
Apr.
16, 18 |
as
above, check out |
|||
|
*Lab
quiz (15 points) will cover significant figures, stoichiometry,
and IR. |
|||||
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