Instructor: Dr. Holly D. Bendorf
Office: 209
Heim Building
Phone: office:
4365 home: 327-2888
e-mail: bendorf@lycoming.edu
Course Schedule: Lecture:
MWF 9:00 - 10:05, Heim G-09
Labs: T 7:45 - 11:35 am,
T 2:00 - 5:50 pm, R 7:45 - 11:35 am.
;
Prelab in Heim 220. Lab in Heim 236.
Office Hours: M 11:00 am - noon, W 10:00 am - 11:00 am, R 2:00 pm - 3:00 pm, and by appointment, or just drop by.
Evening Review Session: To be announced.
Course Description: CHEM 220, Organic Chemistry I, is an introduction to the study of the chemistry of carbon compounds. The course covers the chemistry of alkenes and alkynes, the substitution and elimination chemistry of alkyl halides, the theory and applications of infrared spectroscopy, and the strategies of organic synthesis. The laboratory portion of the course will introduce the student to a variety of techniques for the synthesis, purification, and analysis of organic compounds.
Text and Materials:
"Organic Chemistry" by George Schmid, Mosby Publishers, 1996.
"Study Guide for Organic Chemistry" by Skonieczny and Schmid
(Optional, a copy is on reserve in the library).
Molecular Model Set for Organic Chemistry (Lehman).
Bound laboratory notebook (Freeman).
CHEM 220-221 lab manual.
Safety glasses or goggles.
Lab deposit of $10, refundable upon check-out.
Calculator with logarithmic and exponential functions.
Materials in Chemistry Reading Room: Copies of several organic chemistry texts are available in the reading room (217 Heim Bldg.). If you are not satisfied with Schmid's treatment of a topic, feel free to consult one of the other textbooks--you may just find one you like. These texts are excellent sources of extra practice problems (solutions manuals are available for several of the texts as well).
Grading Criteria: Quizzes
120 points 14%
Brief exam 70 points
8%
Exams 300 points
35%
Laboratory 210 points 25%
Final
150 points 18%
;
850 points 100%
Final letter grades will be assigned as follows: 765-850 A, 680-764 B, 595-679 C, 510-594 D, <510 F. The ranges given include "+" and "-" grades. Be aware that you must pass both the lecture and laboratory to receive a passing grade for the course.
Exams: A brief exam (or you can think of it as a large quiz) will be given on Friday, September 18. There will be three in-class exams on the following dates: Friday, October 9; Friday, November 6; and Friday, December 4. The final exam will be administered on the day and time assigned by the registrar.
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: The course outline (below) lists
reading assignments for each class. I suggest you skim the assignment
before class and then read it more thoroughly afterwards. Problems
related to each reading assignment are also listed. Although the
problems will not be collected, you should complete them before the next
class period. Lectures, quizzes, and in-class exercises are prepared
with the assumption that you have read and understand the assigned material
and have completed the problems.
Review Session: The evening help session is an informal
workshop where you will have the opportunity to ask questions, review lecture
material, and work problems either individually or in groups.
Extra Credit: Extra credit points can be earned by attending departmental colloquia (3 per colloquium). Extra credit points can also be earned by writing a brief research paper on a mutually agreed upon topic (up to 10 points). Other types of extra credit projects may become available during the semester. Extra credit is limited to 20 points.
General Comments:
Attendance: Attendance is mandatory. Three absences
are permitted; additional absences will be penalized (3 points per absence).
Missed quizzes, exams and laboratory meetings can not be made-up unless
the absence has prior approval from me and can be documented (for example,
by a note from student health services or the dean). Make-up quizzes
and exams will not be given. A missed quiz will be recorded as a
grade of zero. Students who miss a mid-semester exam due to an excused
absence (see above) will be given single, cumulative make-up exam at the
end of the semester.
Study Suggestions: Perhaps the best advice I can give you on how to succeed in this course is: Don't get behind! We cover a lot of material in this class and cramming for a night or two before an exam simply won't work. Furthermore, each section builds upon the material covered in the previous chapters and to succeed in this course you need to be fluent with one chapter before moving on to the next. Just like learning a foreign language or becoming proficient at a sport, you need to practice a bit each day. Review your class notes, read the text, discuss the material with your classmates, quiz yourself, and most importantly: work lots of problems. And remember, my job is to help you learn organic chemistry--if you have questions, if you are not sure how to approach a type of problem, or if a concept is still a little fuzzy, ask me about it!
Useful resources on the web:
The on-line catalogs are good sources of information for your lab reports.
We'll talk more about them at the first lab meeting. Yahoo is a good
place to start if you just want to see what's out there as far as chemistry
web sites. There are links to all sorts of sites--some are useful,
humorous or interesting... and some aren't!
Acros Organics Catalog www.acros.be
Yahoo www.yahoo.com/Science/Chemistry
The Lycoming College Department of Chemistry www.lycoming.edu/dept/chem/
Course Outline: The outline is tentative and subject to change.
| Date | Subject | Text | Problems | Q/E |
| Aug. 31 | Intro. to Organic | 1.1-3 | 1.18-20 | |
| Sept. 2 | Electron config., Lewis structures | 1.4-7 | 1.1-5, 21-23 | |
| Sept. 4 | Geometry, Hybridization, and MO's | 1.8-13 | 1.7-11, 25-30, 32-36 | |
| Sept. 7 | Ionic and covalent bonds, electronegativity | 1.14-16 | 1.14, 15, 17, 39-45 | |
| Sept. 9 | Alkanes: properties, isomerism | 2.1-3,8,9,11 | 2.1, 2, 13, 22, 32 | |
| Sept. 11 | Nomenclature of Alkanes and Alkyl Halides | 2.4-7 | 2.4-8, 10-12, 25-30 | quiz |
| Sept. 14 | Functional Groups | 2.12-15 | 2.15, 16, 18-21, 38, 39 | |
| Sept. 16 | Conformations of alkanes | 3.9,10; 4.1-5 | 3.42; 4.1, 4, 16, 19 | |
| Sept. 18 | Mini-exam | exam | ||
| Sept. 21 | Conformations of cycloalkanes | 4.6-11 | 4.6-8, 20, 22 | |
| Sept. 23 | Cyclohexane Conformers | 4.12-14 | 4.9-15, 23-27, 30 | |
| Sept. 25 | Stereochemistry-chirality at carbon | 6.1-7 | 6.1-3, 5, 13-15, 30, 31 | quiz |
| Sept. 28 | Assigning absolute configuration (R/S) | 6.2, 8-10 | 6.6-12, 18, 32-34 | |
| Sept. 30 | Enantiomers, diastereomers, meso forms | 6.10-11 | 6.20, 21, 39-41 | |
| Oct. 2 | Properties, Fischer Projections | 6.12-15 | 6.26, 27, 42-45 | quiz |
| Oct. 5 | Acid/Base Chemistry | 3.1-7 | 3.1-3, 6-12, 14, 16, 31 | |
| Oct. 7 | Resonance and arrow notation | 3.8 & handout | 3.17, 18, 27-30, 38-41 | |
| Oct. 9 | EXAM 1 | EXAM | ||
| Oct. 12 | Kinetics and mechanism | 3.9-14 | 3.19-22, 42, 43 | |
| Oct. 14 | Introduction to Organic Reactions | 3.15-17 | 3.23-25 | quiz |
| Oct. 16 | No Classes | |||
| Oct. 19 | Sn2 reaction: Intro., kinetics, mechanism | 12.1-3 | 12.1, 17, 18 | |
| Oct. 21 | Sn2: leaving group, nucleophile | 12.4. | 12.2-5, 20 | |
| Oct. 23 | The Sn1 reaction, Sn1 vs. Sn2 | 12.5-7 | 12.7, 8, 16, 27 | quiz |
| Oct. 26 | Acid-cat. substitutions, cation rearr. | 12.8, 9 | 12.9, 24, 29, 30 | |
| Oct. 28 | Elimination: The E1; acid cat. elim. | 12.10-11, 16 | 12.10, 12, 13, 22, 28, 32 | |
| Oct. 30 | The E2: mechanism, substrate, stereochem | 12.12-13 | 12.11, 17, 25 | quiz |
| Nov. 2 | E2: stereochem., bulky bases | 12.14-15 | 12.18, 23, 31 | |
| Nov. 4 | E1/E2/Sn1/Sn2 wrap-up and review | 12.17-18 | 12.14, 15, 19, 26 | |
| Nov. 6 | EXAM 2 | EXAM | ||
| Nov. 9 | IR spectroscopy: theory and applications | 5.1-4,7 | 5.2-5, 19 | |
| Nov. 11 | IR spectroscopy, Degree of unsaturation | 5.5,6,11 | 5.6-8, 13-15, 21-24 | |
| Nov. 13 | Alkenes: properties, preparation | 7.1-6, 18 | 7.1-12, 28-31 | quiz |
| Nov. 16 | Alkene reactions: addition of HX | 7.7-13 | 7.14, 16-20, 22, 32-35 | |
| Nov. 18 | Alkene reactions: mechanism, carbocations | 7.14-17 | 7.23-27, 36-41 | |
| Nov. 20 | Alkene reactions: electrophilic addition | 8.1-4,8,9 | 8.1-4, 11-14, 15, 38, 39 | quiz |
| Nov. 23 | Alkene reactions: electrophilic addition | 8.5,6,11,12 | 8.5-8, 20, 23-28, 31, 32 | |
| Nov. 25 | No Classes | |||
| Nov. 27 | No Classes | |||
| Nov. 30 | Alkynes: structure and properties | 9.1-5, 9 | 9.1, 2, 22, 23, 31 | |
| Dec. 2 | Alkynes: electrophilic addition | 9.6-8 | 9.3-12, 24 | |
| Dec. 4 | EXAM 3 | EXAM | ||
| Dec. 7 | Alkynes: acid-base chemistry | 9.10-11 | 9.14-17, 26, 28 | |
| Dec. 9 | Synthesis | 9.12. | 9.18, 19, 25, 27 | quiz |
| Dec. 11 | Synthesis | 9.20, 29, 30 | ||
| Exam Week: |
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)
and/or dismissal from the lab.
The laboratory grade is worth a total of 210 points and is comprised
of ten lab write-ups (170 points total) and two lab quizzes (40 points).
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 Outline:
| Week | Dates | Lab | Assigned Reading | Report due for week:* |
| 1 | Sep. 1, 3 | Check-in | Chp. 1 | |
| 2 | Sep. 8, 10 | Melting Points | Chp. 2, 4, 5 | |
| 3 | Sep. 15, 17 | Distillation | Chp. 6, 7 | 2 |
| 4 | Sep. 22, 24 | Recrystallization of Benzoic Acid and Naphthalene | Chp. 8-10 | 3 |
| 5 | Sep. 29 & Oct. 1 | Solubility Testing and Unknown Recrystallization | Chp. 3, 8-10 | 4 |
| 6 | Oct. 6, 8 | Unknown Recrystallization | Chp. 14, 8-10 | |
| 7 | Oct. 13, 15 | Nucleophilic Competition | Chp. 19, 21 Quiz 1 | 5, 6 |
| 8 | Oct. 20, 22 | Extraction and GC of Nuc. Comp. | Chp. 11-13 | |
| 9 | Oct. 27, 29 | Extraction | Chp. 11-13 | 7 |
| 10 | Nov. 3, 5 | Dilantin, Part 1 | Chp. 16-18 | 8, 9 |
| 11 | Nov. 10, 12 | Dilantin, Part 2 | Chp. 16-18 | 10 |
| 12 | Nov. 17, 19 | Cyclohexene | Chp. 15 Quiz 2 | 11 |
| 13 | Nov. 24, 26 | Thanksgiving--No Labs | ||
| 14 | Dec. 1, 3 | Steam distillation of Limonene | Chp. 23, 25 | 12 |
| 15 | Dec. 8, 10 | Limonene Characterization, and Check-out | Chp. 24 | 14, 15 |
Last updated September 1, 1998.
The URL for this page is
http://lyco2.lycoming.edu/dept/chem/fall1998/220syl.htm