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 keys, old tests, and exam study guides (www.lycoming.edu/chem/fall2001/220/22001keyfront.htm).

Fall 2001  Organic Chemistry 1 Lycoming College

Course description - This course is designed to introduce the student to the chemistry of alkanes, alkenes, alkynes, and alkyl halides.The approach will be both mechanistically and synthetically oriented.The laboratory component of this course will involve the basic techniques of synthetic organic chemistry.


Dr. Chriss McDonald*lectures, lab, recitationsHBC 233

*321-4186 (work), 433-4493 (home, please feel free to call me up to 10 PM), or e-mail (mcdonald@lycoming.edu)

Texts etc.

a.Organic Chemistry,5th ed by McMurry#

b.Chemistry 220 Lab Manual, by McDonald, Bendorf, and Berkheimer (sold by Laura Riel, our new secretary)

c.Bound laboratory notebook by Freeman#

d.Lab safety glasses (sold by Chem Club)

e.Calculator (add, subtract, multiply, divide, logs)#

f.Lab deposit, $10 at lab check-in, cash only (refundable upon checkout)

#available at the bookstore

Course format

Lectures - MWF, 9:00 – 10:05, HBC G09, Attendance required.

Recitations – Problem solving sessions will be built into class time.We will also have a weekly help session in the evening (starting week 2).

Assigned homework - Problems designed to enhance your understanding and prepare you for testing situations.A key will be posted on the web and outside my office.Homework will not be collected.

Web-based supplements- 

a.Organic Chemistry Online CD in your text (problems and tutorials)

b.Homework keys, old tests, and exam study guides (www.lycoming.edu/chem/fall2001/220/22001keyfront.htm);

c.www.chemfinder.camsoft.com great for looking up physical property info for lab writeups;

d.Departmental homepage- many links to useful chemistry info;

e.Chemical drawing program for your computer! www.mdli.com/cgi/dynamic/welcome.html (click on download center then click on Isis/Draw.

Laboratory - T: 7:45 – 11:35 pm; Tuesday,U:1:00 – 4:50 pm, Tuesday; X: 7:45 – 11:35 pm, Thursday,HBC 220, 234.Attendance required.Here you will experience what chemists actually do.Your labwork will be evaluated as described in the lab syllabus as well as on the lecture exams.Approximately 5% of each exam will be drawn from the labwork.A lab syllabus will be distributed at the first lab session.Make sure and show up with your $10 lab deposit (cash only) that first week.Meet at 9:30 for morning lab sections this first week.

Grading scheme

a.The final grade is based on the number of points obtained out of a possible 586 points.The points will bedistributed as follows:

quizzes70 points (12%)

exam 185 points (15%)

exam 2100 points (17%)

exam 3100 points (17%)

final exam (cumulative)*120 points (21%)

laboratory110 points (19%)

total585 points (100%)

*a higher score on the final exam can be used to replace a lower score from exam 1-3.

As always you will have the opportunity to obtain bonus points through attendance at our colloquium series.Assuming you stay for the whole show and you mind your manners you will receive 3 points per colloquium.You may also receive up to 8 bonus points by writing a paper on a topic that we have mutually agreed upon (2-3 pages, typewritten, double spaced, with a minimum of 2 bibliographic sources.The ceiling on bonus points (excluding bio assignment and those on exams) is 15.

b.Assignment of letter grades is based on the following scale:527 - 585 A, 468 - 526 B, 410- 467 C, 351 - 409 D, < 351 F.

c.A word about learning chemistry.Studying chemistry is hard work for most people (this is certainly true for me).I would recommend that you work on the lecture material one hour per day every day outside of class for starters (note that there are 7 days in a week).Once you see how things are going this amount can be adjusted as needed (I suggest a significant increase in study time prior to an exam).If you are having trouble make sure and come and see me.I’m easy to talk to and will do whatever I can to help you.You will be responsible for all of the material listed on the following schedule for the indicated exams and quizzes.It is not sufficient to learn the material from the lecture alone.You are expected to read and think about the material prior to the lecture.We must necessarily cover a large amount of material so our pace must be geared towards those who are ready to learn.The hour exams will be somewhat cumulative in the sense that you will need to know the earlier material to comprehend the latter.

Policy on attendance

Attendance at quizzes and exams is mandatory.Makeups will be administered only if I deem the reason for absence to be legitimate and I am made aware of the absence beforehand.Each documented, unexcused lecture absence beyond the first two will cost you one point from your total.

Lycoming CollegeOrganic Chemistry 1Fall 2001


“Organic Chemistry nowadays almost drives me mad.To me it appears like a primeval tropical forest full of the most remarkable things, a dreadful endless jungle into which one does not dare enter, for there seems no way out.”

Freidrich Wohler, 1835

(the slayer of the vital force theory)


8/27hello organic chemistry!Preface, 1 (p. 1-3)

8/29ionic,covalent bonds,Lewis structures1.1, 4,5

8/31formal charge,functional groups2.1-3,12,13, 3.1

9/3introductory molecular orbital theory1.2,3,6,7

9/5orbital hybridization1.8-11QUIZ 1

9/7as above1.8-11

9/10acid-base reactions2.4-10, 24.4

9/12curved arrow formalism in acid-base rxns2.11QUIZ 2

9/14classification of organic reactions5.1-5

9/17polar reaction examples5.6

9/19EXAM 1 (85 points)-EXAM 1

9/21basic thermodynamics/kinetics5.7-10

9/24naming/drawing alkanes3.2-4

9/26alkane properties, cycloakanes3.5-8

9/28alkane conformational issues4.1-3

10/1ring strain, cycloalkane conformers4.4-13

10/3structure/nomenclature of alkenes6.1,3-5,7QUIZ 3

10/5addition of HX to alkenes-6.8-10

10/8as above + cation rearrangements6.11,12

10/10addition of X2, halohydrin formation7.2-3QUIZ 4

10/12oxymercuration, hydroboration7.4,5

10/15other alkene rxns(bendorf)7.7,8

10/17alkyne nomenclature/structure additions to alkynes8.1,2QUIZ 5

10/19long weekend-

10/22alkyne HX, X2 additions8.4

10/24EXAM 2 (100 points)-EXAM 2

10/26alkyne hydrations, reductions(last day to drop)8.5,6 


1031optical activity9.4,5

11/2sequence rule9.6,6.6


11/7stereochemical analysis of selected rxns9.15-17QUIZ 6

11/9infrared spectroscopy:theory12.5,6

11/12infrared spectroscopy:interpretation24, Lab Manual QUIZ 7

11/14infrared spectroscopy:interpretation6.2, 12.7-9

11/16kinetics/ stereochemistry of substitution11.1-3

11/19the SN2 rxn11.4,5



11/26the SN1 rxn11.6-9

11/28EXAM 3(100 points)-EXAM 3

11/30the E2 rxn11.10-12

12/3the E1 rxn, summary of substitution and elimination11.14,15

12/5alkylation of alkyne conjugate bases8.8,9, 11.16

12/7multistep syntheses, pheromones8.10

12/10Final Exam Week (120 points)



18/28,30Intro, check-in-Chp. 1-3
29/3,6Simple and fractional distillation -Chp. 6, handout

39/11,13Recrystallization2 (distillation)Chp. 8-10

49/18,20Recrystallization3 (recrystallization 1)Chp. 8-10, 4

59/25,27Extraction-Chp. 11, 13,12QUIZ 1

610/2,4Finish extraction4 (recrystallization 2)Chp. 11,13, 

710/9,11Synthesis of Isoamyl acetate5,6 (extraction)Chp. 14,16, handout

810/16,8Synthesis of benzil7 (isoamyl acetate)Chp.17,18

910/23,25Synthesis of dilantin-Chp. 18

1010,30,11/1Finish dilantin8 (benzil)Chp. 18QUIZ 2

1111/6,8 Steam distillation of limonene9,10 (dilantin)Chp. 23, 25

1211/13,15Finish limonene-Chp. 24, 25

1311/27,29E2 Elimination Using Various Bases11,12 (limonene)Chp. 26, 19

1412/4,6finish E2 elimination, check-out14 (E2, in class)Chp. 26, 19

GRADING:The lab component ofyour grade is 110points out of the 585 for the course.There will be 9grades for writeups, 10points each, for 90 points.A typical grade for a writeupcan be broken down into three parts:content of the writeup (60%), yield of the product (20%), purity of the product (20%).Late lab writeups will cost you 5%per school day.There will also be two 10 point lab quizzes.Students who do not conform to our notions of laboratory etiquette (Chp 1, p 2in the lab manual) can expect to have points deducted from their lab score.This can be done either within individual writeups for isolated incidents or as a deduction from the total score for semester-long offenses.In cases where common areas of the lab (balances, melting point apparatus.....) are abused or left messy, an entire lab section may have points deducted.

USEFUL SUPPLEMENTARY SOURCES:One part of your lab writeup requires you to list several physical properties for the compounds involved in that particular experiment.This information can be obtained most conveniently from one of the following:

1)The Merck Index - located in the lab, the reading room, and the library reference collection (RS.51);

2)The CRC Handbook of Chemistry and Physics - located in the lab, the reading room, and the libraryreference collection (QD.65);

3)The Aldrich Catalog - located in the lab and the reading room;

4)The Acros Catalog – located in the lab;

5)The Dictionary of Organic Compounds - located in the reading room;

6)Lange’s Handbook of Chemistry - located in the reading room;


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