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.
FacultyResponsibilitiesOffice
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
Schedule
“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)
datetopictextquiz/exam
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
10/29enantiomerism9.1-3
1031optical
activity9.4,5
11/2sequence
rule9.6,6.6
11/5diastereomers9.7-10
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
11/21Tgiving
11/23Tgiving
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)
ORGANIC
CHEMISTRY 1
LAB
SCHEDULE, FALL 2001
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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Last updated September 3, 2001.