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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.


LYCOMING COLLEGE CHEMISTRY 220 FALL 1998


 CHEMISTRY 220
 FALL 1998 SYLLABUS

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 9Friday, 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

              Aldrich Catalog     pipeline2.sial.com/pubcatalog.nsf
              Alfa Aesar             www.alfa.com

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:         
The final exam will be given on the date and time assigned by the registrar. No exceptions!

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
*Late reports will be penalized 3% per school day.  Lab quizzes are during week 7 and week 12.
More info on lab safety, procedures and reports will be given at the first lab meeting.


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    Last updated September 1, 1998.
    The URL for this page is http://lyco2.lycoming.edu/dept/chem/fall1998/220syl.htm