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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. Some useful web sites for
NMR practice can be found at www.chem.ucla.edu/~webspectra/
and www.nd.edu/~smithgrp/structure/workbook.html.
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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