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Chemistry 26200 Organic Laboratory Spring 2008 |
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Instructor: Prof. George John (john@sci.ccny.cuny.edu) |
Room: Marshak 1237, Tel (212) 650-8353 Office hours in MR 1237 on W: 3-4 and
F: 3-4 or by appointment. |
Catalog Description:
Exercises involving the
preparation and purification of carbon compounds (for non-Chemistry majors).
Prerequisites: Chem
10401 and 26100
Co-requisites: Chem
26300
Hours/Credits:
4 hours per week, 2 cr.
Course objectives:
1. To learn several fundamental organic laboratory techniques
used for purification of compounds, separation of reaction mixtures, monitoring
the course of the reactions and analyzing reactions mixtures and products.
2.
To understand physical
principles underlying each of these techniques.
3.
To perform in practice some
of the fundamental organic reactions by synthesizing a set of compounds and to
apply the techniques learned to these.
The purpose of these synthetic preparations is multiple: to review basic
organic reactions and reinforce the mechanisms learned in the organic theory
courses Chem 261 and Chem 263; to learn how to set up organic reactions (which
includes basic calculations: calculation of limiting reactant and theoretical
yield before the reaction and actual percent yield after the reaction); to learn
how to monitor the progress of the reaction; to learn how to isolate and purify
the product(s) from the reaction, using techniques mentioned above and to
understand and prepare separation schemes for the reactions which they perform
in the lab
4.
To learn safety
precautions (before performing the reactions students are required to compile
data on all reagents that are used in a particular experiment and all the
necessary safety precautions that need to be addressed when using these
reagents).
5.
To learn how to write a
valid laboratory report, which includes: Compiling the data on reagents,
calculating limiting reactant and yields, writing the mechanism of the
reaction, writing the isolation and/or the separating scheme, concisely and
faithfully reporting all the observations during the experiment and analyzing
and reporting the data obtained in the course of the experiment.
Topics covered:
Laboratory
and analytical techniques that are taught in this course include: simple,
fractional and vacuum distillation; extraction; crystallization; chromatography techniques namely: gas chromatography, thin layer
chromatography, liquid chromatography; IR spectroscopy.
Synthetic experiments that are performed are as follows: oxidation
reaction (of cyclohexanol), SN1
reaction (synthesis of t-butyl chloride),
E1 reaction (synthesis of alkenes),
electrophilic aromatic substitution (nitration of phenol), reaction of a
metallocene (acetylation of ferrocene),
esterification reaction (aspirin synthesis), condensation reaction (Aldol), organometallic reaction (Grignard).
Laboratory Manual Chemical
Education Resources (available from the Bookstore)
Lecture Monday (1EG): 2:00-2:50
PM Rm. NA 4/205 (John)
Monday (1HW): 6:00-6:50 PM Rm. NA 4/205 (John)
Friday
(5DF): 12:30-1:20
PM Rm. NA 4/205 (John)
Laboratory Monday (1EG): 3:00-5:50
PM Rm. MR 1113
Monday (1HW): 7:00-9:50 PM Rm. MR 1109
Lecture Attempts
have been made to provide good relevant learning experiences in an organic
chemical laboratory. Theoretical material relevant to the experiments will be
discussed in the lecture and this can supplement information pertaining to the
experiment itself. The lecture
will endeavor to explain techniques, relevance and applications of these,
reactions, mechanisms and other information related to the experiments at
hand. Each experiment in the lab
manual explains background information pertinent to that experiment. In a few cases the information
pertaining to the experiment will be provided in the lecture and/or laboratory
since the lab manual does not contain this. Students are strongly encouraged to study this information
prior to the lectures.
Schedule The attached schedule shows the
experiments that will be performed and dates for the exams. There will be unannounced quizzes on material already covered (i.e. there
will be no material on the quiz that has not been visited in the previous
lectures).
Grading There
are a total of 13 experiments, some relate to techniques, some to reactions and
mechanisms, and some are aimed at synthesis of compounds. Of the 13 experiments the best 12 will
be used in computing the final grade.
Laboratory reports for each experiment must be handed in no later than one week after completion of that experiment.
There will be one mid-term exam (worth 75 points) and one final (worth 100 points).
There will be 6 unannounced quizzes (each
worth 10 points). These will be
administered at the beginning of a lecture. Of these, the best 5 quiz grades will be used for
calculation of the final grade.
Student performance will be evaluated by
the TA and is worth a total of 25 points.
A summary of the points assigned to each portion of the course is shown
below. Note that the exams and
quizzes constitute ~40% of the grade while the laboratory activities constitute
~60%.
Experiments 13 in all, best
12/13 x 25 points each =
300 points
Quizzes 6 in all, best 5/6
x 10 points each =
50 points
Mid-term exam, 75 points =
75 points
Final exam (comprehensive), 100 points =
100 points
TA evaluation, 25 points =
25 points
There are no makeup labs and no
makeup exams or quizzes. Absence
without a strong, verifiable, documented reason will result in zero points for
the material missed. Lab reports
not submitted in a timely manner will also result in zero points for that
exercise.
Safety issues You
must wear lab goggles at all times in the lab. Do not wear shorts or short skirts without a lab coat, this
is for your safety! Similarly,
open shoes and slippers should not be worn. You are strongly
encouraged bring your own latex gloves to the lab. YOUR workplace should be
CLEAN always!
Breakage Students must be aware of the fact that
they will be charged for the replacement cost of any equipment that they break
during the lab course. Some of the
glassware is especially expensive and so you are urged to work carefully at all
times.
If you have questions, comments or suggestions please contact your teaching assistant or the instructor.
Academic integrity The
CCNY policy on academic integrity will be followed. Document is posted on the
CCNY website (CUNY policy on academic integrity—link is at the bottom of
the home page). Make sure you have read the details regarding plagiarism and
cheating, in case you are not clear about the rules of the college. Cases where
academic integrity is compromised will be prosecuted according to these rules.
Laboratory
reports
All
your lab work should be recorded in a lab notebook and not on scraps of paper. Data recorded in the
notebook must be properly dated, and neatly written. Based on this information, you will generate a laboratory
report that will be submitted for grading. This exercise provides experience with accurate data management
and report writing. A general
format for the laboratory report is provided below.
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1. |
On
the top right hand side please write your name, ID number and section number
(under each other). |
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2. |
Title
of the experiment you will be performing. |
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3. |
The
aim of the
experiment. |
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4. |
Any
equations or chemical structures relevant to the experiment as well as any
pertinent mechanisms. |
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5. |
A
table listing the compounds you will be using/preparing, their molecular
weights, amounts used in grams and moles, boiling or melting points and the
densities (for liquids), as applicable. |
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6. |
Hazards:
determine the flammability, toxicity or corrosiveness of the compounds you
will be using in that particular experiment. Please be sure to list a reference for the source of the
information. This can be listed
in a separate column in 5 above. |
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7. |
Procedure
and Observations. Please
describe exactly how you performed the experiment and exactly what
observations were made (eg. color changes, if any spillage occurred etc). The observations have to be very
specific. Write any separation
schemes or flowcharts. Always
write the procedure in the third person and in the past tense. |
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6. |
Results. This part should include
identification of the limiting reagent and calculation of the theoretical
yield of the product. Actual
yield of the product (weight and percentage yield), graphs (if any), physical
properties of the compound such as color or nature of the product (eg.
colorless needles of compound X were obtained). Melting or boiling points. Inferences from specific observations
that you were required to make. |
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7. |
Conclusions. Did you achieve what had to be
achieved? Did you have any
problems, discuss these. Other
scientific comments on the experiment, such as suggestions if you feel you
could do something differently to improve the experiment. |
To
complete items 5 and 6 of the prelab report you will need information on
reagents listed in the lab procedure.
Information for these chemicals can be obtained from a number of
sources. The most common resource
for this information is the CRC Handbook of Chemistry and Physics, the Material
Safety Data Sheets or the Aldrich catalog. Several sources can be found in the library. There are also a number of sources for
this information online. A page listing these sources has been assembled by the
campus science librarian at the url:
http://www.ccny.cuny.edu/library/divisions/science/chems.htm
or, http://physchem.ox.ac.uk:80/MSDS/
The City College of New York-
Department of Chemistry
Chemistry 26200-Organic Chemistry Laboratory-Spring
2008
Section 1EG: Lecture: Room
NA 4/205: M-2:00-2:50 pm; Lab: Room MR 1113: M-3:00-5:50 pm
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Week 1 Jan 28, MON |
Introduction, Check In, Measuring
Melting Points of Compounds and Mixtures |
TECH 701 |
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Week 2 Feb 04, MON |
Purifying Acetanilide by
Recrystallization |
TECH 703 |
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Week 3 Feb 11, MON |
Separating Cyclohexane and Toluene
by Distillation |
TECH 704 |
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Week 4 Feb 25, MON |
Separating Acids and Neutral
Compounds by Solvent Extraction |
TECH 705 |
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Week 5 Mar 03, MON |
Separating Ferrocene and
Acetylferrocene by Adsorption Column Chromatography |
TECH 708 |
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Week 6 Mar 10, MON |
Gas Chromatography and Thin Layer
Chromatography |
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Week 7 Mar 17, MON |
Brominating Alkenes (Group 1);
Identifying an Unknown Compound by Infrared Spectroscopy (Group 2) |
TECH 719
TECH 710
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Week 8 Mar 26, WED |
Brominating Alkenes (Group 2);
Identifying an Unknown Compound by Infrared Spectroscopy (Group 1) |
TECH 719 TECH 710 MID-TERM EXAM
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Week 9 Mar 31, MON |
Qualitative Test for Alkenes and
Identifying an Unknown Compound by Infrared Spectroscopy |
TECH 472 |
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Week 10 Apr
07, MON |
Studying SN1 and SN2
Reactions: Nucleophilic Substitution at Saturated Carbon |
REAC 714 |
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Week 11 Apr
14, MON |
Dehydrating Cyclohexanol |
REAC 712 |
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Week 12 Apr
28, MON |
Nitrating Methyl Benzoate |
REAC 716 |
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Week 13 May 5, MON |
The Aldol Condensation: Synthesis
of Dibenzylacetone |
SYNT 720 |
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Week 14 May 12, MON |
Equipment Check Out |
FINAL EXAM
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