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 1:00 - 4:50 pm, R 7:45 - 11:35 am.
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Prelab in Heim 220. Lab in Heim 236.
Office Hours: M& 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:
| Grading Criteria: | Quizzes | 105 points | 16% |
| Exams | 300 points | 44% | |
| Laboratory | 105 points | 16% | |
| Final | 160 points | 24% | |
| 670 points | 100% |
Exams: There will be three in-class exams on the following dates: Friday, October 1; Friday, October 29; and Monday, November 22. 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 18 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.com
Yahoo www.yahoo.com/Science/Chemistry
| Date | Subject | Text | Problems | Q/E |
| Aug. 30 | Intro. to Organic | 1.1-3 | 1.18-20 | |
| Sept. 1 | Electron config., Lewis structures | 1.4-7 | 1.1-5, 21-23 | |
| Sept. 3 | Geometry, Hybridization, and MO's | 1.8-13 | 1.7-11, 25-30, 32-36 | |
| Sept. 6 | Ionic and covalent bonds, electronegativity | 1.14-16 | 1.14, 15, 17, 39-45 | |
| Sept. 8 | Alkanes: properties, isomerism | 2.1-3,8,9,11 | 2.1, 2, 13, 22, 32 | |
| Sept. 10 | Nomenclature of Alkanes and Alkyl Halides | 2.4-7 | 2.4-8, 10-12, 25-30 | quiz |
| Sept. 13 | Functional Groups | 2.12-15 | 2.15, 16, 18-21, 38, 39 | |
| Sept. 15 | Conformations of alkanes | 3.9,10; 4.1-5 | 3.42; 4.1, 4, 16, 19 | |
| Sept. 17 | Conformations of cycloalkanes | 4.6-11 | 4.6-8, 20, 22 | quiz |
| Sept. 20 | Cyclohexane Conformers | 4.12-14 | 4.9-15, 23-27, 30 | |
| Sept. 22 | Stereochemistry-chirality at carbon | 6.1-7 | 6.1-3, 5, 13-15, 30, 31 | |
| Sept. 24 | Assigning absolute configuration (R/S) | 6.2, 8-10 | 6.6-12, 18, 32-34 | quiz |
| Sept. 27 | Enantiomers, diastereomers, meso forms | 6.10-11 | 6.20, 21, 39-41 | |
| Sept. 29 | More fun with stereochemistry! | |||
| Oct. 1 | EXAM 1 | EXAM | ||
| Oct. 4 | Properties, Fischer Projections | 6.12-15 | 6.26, 27, 42-45 | |
| Oct. 6 | Acid/Base Chemistry | 3.1-7 | 3.1-3, 6-12, 14, 16, 31 | |
| Oct. 8 | Resonance and arrow notation | 3.8 & handout | 3.17, 18, 27-30, 38-41 | |
| Oct. 11 | Kinetics and mechanism | 3.9-14 | 3.19-22, 42, 43 | |
| Oct. 13 | Introduction to Organic Reactions | 3.15-17 | 3.23-25 | quiz |
| Oct. 15 | Sn2 reaction: Intro., kinetics, mechanism | 12.1-3 | 12.1, 17, 18 | |
| Oct. 18 | Sn2: leaving group, nucleophile | 12.4. | 12.2-5, 20 | |
| Oct. 20 | The Sn1 reaction, Sn1 vs. Sn2 | 12.5-7 | 12.7, 8, 16, 27 | quiz |
| Oct. 22 | No Classes | |||
| Oct. 25 | Acid-cat. substitutions, cation rearr. | 12.8, 9 | 12.9, 24, 29, 30 | |
| Oct. 27 | Elimination: The E1; acid cat. elim. | 12.10-11, 16 | 12.10, 12, 13, 22, 28, 32 | |
| Oct. 29 | EXAM 2 | EXAM | ||
| Nov. 1 | The E2: mechanism, substrate, stereochem | 12.12-13 | 12.11, 17, 25 | |
| Nov. 3 | E2: stereochem., bulky bases | 12.14-15 | 12.18, 23, 31 | |
| Nov. 5 | E1/E2/Sn1/Sn2 wrap-up and review | 12.17-18 | 12.14, 15, 19, 26 | |
| Nov. 8 | IR spectroscopy: theory and applications | 5.1-4,7 | 5.2-5, 19 | |
| Nov. 10 | IR spectroscopy, Degree of unsaturation | 5.5,6,11 | 5.6-8, 13-15, 21-24 | quiz |
| Nov. 12 | Alkenes: properties, preparation | 7.1-6, 18 | 7.1-12, 28-31 | |
| Nov. 15 | Alkene reactions: addition of HX | 7.7-13 | 7.14, 16-20, 22, 32-35 | |
| Nov. 17 | Alkene reactions: mechanism, carbocations | 7.14-17 | 7.23-27, 36-41 | quiz |
| Nov. 19 | Alkene reactions: electrophilic addition | 8.1-4,8,9 | 8.1-4, 11-14, 15, 38, 39 | |
| Nov. 22 | EXAM 3 | EXAM | ||
| Nov. 24 | No Classes | |||
| Nov. 26 | No Classes | |||
| Nov. 29 | Alkene reactions: electrophilic addition | 8.5,6,11,12 | 8.5-8, 20, 23-28, 31, 32 | |
| Dec. 1 | Alkynes: structure and properties | 9.1-5, 9 | 9.1, 2, 22, 23, 31 | |
| Dec. 3 | Alkynes: electrophilic addition | 9.6-8 | 9.3-12, 24 | quiz |
| Dec. 6 | Alkynes: acid-base chemistry | 9.10-11 | 9.14-17, 26, 28 | |
| Dec. 8 | Synthesis | 9.12. | 9.18, 19, 25, 27 | |
| Dec. 10 | 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 | Aug. 31; Sep. 2 | Check-in | Chp. 1 | |
| 2 | Sep. 7, 9 | Distillation | Chp. 6, 7 | |
| 3 | Sep. 14, 16 | Recrystallization of Benzoic Acid and Naphthalene | Chp. 4, 8-10 | 2 |
| 4 | Sep. 21, 23 | Solubility Testing and Unknown Recrystallization | Chp. 2, 3, 8-10 | 3 |
| 5 | Sep. 28, 30 | Unknown Recrystallization | Chp. 14, 8-10 | |
| 6 | Oct. 5, 7 | Extraction | Chp. 11-13, Quiz 1 | 4, 5 |
| 7 | Oct. 12, 14 | Extraction | Chp. 11-13 | |
| 8 | Oct. 19, 21 | Nucleophilic Competition | Chp. 19, 21 | 6, 7 |
| 9 | Oct. 26, 28 | E1 Elimination | Chp. 16, Handout | 8 |
| 10 | Nov. 2, 4 | E2 Elimination | Chp. Handout, Quiz 2 | 9 |
| 11 | Nov. 9, 11 | Dilantin, Part 1 | Chp. 16-18 | 10 |
| 12 | Nov. 16, 18 | Dilantin, Part 2 | Chp. 16-18 | 11 |
| 13 | Nov. 23, 25 | Thanksgiving--No Labs | ||
| 14 | Nov. 30; Dec. 2 | Limonene | Chp. 23-25 | 12 |
| 15 | Dec. 7, 9 | Limonene Characterization, and Check-out | Quiz 3 | 14, 15 |
Last updated September 1, 1999.
The URL for this page is http://lyco2.lycoming.edu/dept/chem/fall1999/220syl.htm