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CHEM 307.001,002 Laboratory syllabus
Coppin State College. Department of Natural Sciences
Organic Chemistry I
Fall Semester,
Dr. Amah
LABORARORY SYLLABUS
A. Safety Goggles Required
Maryland State Law, College regulations, and Departments policy require that
safety goggles must be worn at all times in the lab. This applies to you when
you are in the lab even though you may not be working at the time. It is
recognized that wearing safety goggles may be uncomfortable, but keep in mind
that being blinded or having impaired vision for life is likely to be less enjoyable.
Unlike many chemical reactions, eye damage is irreversible! Please cooperate.
This safety goggle requirement is for your own good. You may be and excellent,
safety laboratory worker, but a student near you may be a disaster in lab.
Students not wearing safety goggles when required to do so may, at the
option of the instructor, be dismissed from lab and allowed to make up the
missed work. As a consequence, such students will not be able to hand in
the laboratory report on that experiment and thus fail the course.
B. Laboratory Safety, Equipment and Waste Disposal
Safety in working in the laboratory, in working with chemicals and equipment,
and in working with other students is of great importance. Please reach the
following very carefully.
I.
Laboratory Safety: Safety work in the laboratory is vitally important to
you and others working in the laboratory. Read Zubrick, Chapter 1. We
emphasize and enforce laboratory safety. Lab lectures will provide
detailed instructions for the proper and safe methods of conducting
experiments.
II.
Laboratory Equipment: Commonly used laboratory equipment and
apparatus are shown and their use described in the lab text. Read
Zubrick, Chapters 4, and 6. You will use many of these items during the
semester. When experimental procedures require the use of equipment
that is unfamiliar to you, refer to these chapters.
III.
Cleaning Glassware: Use care in handling glassware. Check each piece
of glassware for chips or cracks before using it. If in doubt, ask your
instructor. Heating or using cracked glassware is dangerous. Even though
we not charge for glassware that is broken, we do ask your cooperation in
handling it with respect and care.
IV.
Hazardous Waste Disposal: We place great emphasis on the proper
disposal of all the waste generated by students taking organic chemistry.
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One hood in the lab is devoted to the storage of containers in which
various types of waste are to be placed. You will be instructed about the
proper disposal of waste that results from experiments you perform and
which waste container to use for disposal of waste. If in doubt, consult
your instructor. Please do your part to minimize the pollution of our
environment.
V.
Safety Equipment and Emergency Exits: Become familiar with the
location of safety equipment (fire extinguishers and safety shower) in the
laboratory. Your instructor will show these to you and will instruct you
about exits from lab and building in case of emergency.
C. Pre-Lab Exercises
Pre-lab Exercises are contained in the CHEM 307 Supplements. Due date are
given in the Semester Calendar. Pre-lab exercises are due at the beginning of
lab period. Late pre-lab exercises will receive a grade of “0”. You will find the
answers to these exercises in one or more of the following: (a) assigned reading
for experiment; (b) experimental procedure(s); (C) section J in this syllabus; and
(D) “For Your Safety” section of those experiments contained in the CHEM 307
Supplements.
D. How to Prepare for Laboratory Work
Successful completion of the assigned lab work requires study and preparation
before coming to lab. This is essential so that you can be well-organized in your
work. Have well in mind what you are going to do before coming to lab. Plan
ahead.! It will save you lot of time and permit you to complete the lab work on the
allotted time. It will also have added benefit of your understanding WHAT you are
doing and WHY you are doing it. Material must be prepared and written in your
lab notebook before coming to lab and is discussed in Section E of this syllabus.
Your notebook may be checked at any unannounced time to ensure that you
have prepared it in advance.
E. Advance Preparation and Lab Notebook
You must keep a notebook in lab and must use it to recall your data and other
pertinent facts relating to your work. Two different “types” of experiments are
done in CHEM 307 laboratory this semester: Investigative, and Preparative.
The following indicates what to write in your notebook before coming to lab. You
should also have a Table of Contents at the front of the notebook that you keep
up to date. The Sec. J in this lab syllabus indicates which experiments are
Preparative and which are Investigative. All data must be written in your lab
notebook and therefore will be on the data sheets you hand in (Section F)
The same data must be written in your lab Reports(Section H). State each
new experiment on a new notebook page.
(a) Investigative Experiments
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For each investigative experiment, write the following in your notebook BEFORE
coming to lab.
(1) Title of Experiment and References
(2) Introduction-one or two sentences is sufficient
(3) Experiment to be Performed-List, in statement form (one or two lines is
adequate), for each experiment to be performed. Leave adequate space or
room to record your data and results.
(b) Preparative Experiments
The information shown in “Preparative Experiments, Part I” in CHEM 307
Supplements must be written in your laboratory notebook BEFORE you come to
lab.
F. Materials to Be Handed in From Laboratory Notebook
At the conclusion of each experiment, hand in the carbon copy from the
laboratory notebook for the work you have done for the entire experiment.
Staple the sheets together. Use your notebook to record data, and keep it in a
logical order so that you and your instructor can identify it.
G. Before Leaving Lab Each Period
When you are ready to leave lab, clean all glassware and make sure you have all
equipment and glassware in the correct locker. Remember to put all clamps,
clamp holders, and iron rings in the correct locker. Glassware that you use in lab
must be cleaned at all times. Your instructor will inspect your area of work check
and initial your notebook before you leave. Failure to have your notebook
initialed and checked out before you leave will reduce the grade on the laboratory
report for that experiment.
H. Laboratory Reports
 Laboratory reports for each experiment must be handed in. One or more
missing laboratory reports will result your getting a grade of “F” in the course.
 Laboratory reports must contain the data that you have recorded in your
notebook and therefore be on the data sheets you handed in at the completion of
each experiment. Laboratory reports will penalized if they contain data that is
different from or missing from the data sheets.
 Laboratory reports are to be written in a clear, concise, readable form in ink on
8-1/2 – 11” paper. Write on ONE SIDE of paper only! Typed or word
processed reports are required. The reports should contain the data you
recorded in your notebook, even though you have handed in the data sheets.
Late reports will be penalized at least by 10 points. Be sure that your final
reports include the material requested in Section J. Keep the reports brief and to
the point; please do not rewrite the material given in the lab text or handouts.
Before writing the reports, see the “Laboratory Report” discussion for each
type of experiment: Investigative or Preparative.
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(a)
Investigative Experiments
(1) Title of Experiment and References
(2) Introduction: several sentences are sufficient.
(3) Conclusion/Comments: State what you learned from the experiment an how
it relates to the theories and techniques of organic chemistry. List three(3)
experimental problems, including reasons, that may have been encountered
in the experiment.
(b) Preparative Experiments
See “Preparative Experiment, Part II” in CHEM 307 Supplements for a sample
for laboratory reports for preparative experiments.
I. Laboratory Grading
To pass the course, you must pass the lecture and laboratory portions of the
course with a grade of D or better. All laboratory work will be assigned
numerical grades, whose letter grades translation is: A = 90-100; B = 80-89; C
= 70-79; D = 60-69. All laboratory experiment must be performed, and you
must submit a written laboratory report on each experiment. Failure to
hand in one or more laboratory reports will result in your getting an “F” in
the course.
J. Experiments and Comments
These section contain the information about the experiments that you will
perform this semester. Included are the reading assignments from the lab text
and/or the lecture text. Experiments are designed as being “Preparative” or
“Investigative” to allow you to determine the format for your notebook and the
laboratory report for each experiment. Please read these comments carefully
before preparing for an experiment and writing the laboratory report.
Label Compound: When handling in liquids or solids from any experiment, label
your sample vials with the following information:
Your Name
CHEM 307, Sec. #, Instructor
Name of Content
Yield: weight in g
Bp or mp of content
Hand in Compounds: Unless directed otherwise, compounds must be handed
in. Failure to do so will result in a 10-point penalty on the laboratory report.
(a) Recrystallization: Read Zubrick Chapters 13, and 17.
Experiment:
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You will be given an unknown solid to purify by recrystallization from water. The
unknown will be either benzamide (mp 130-131 0C) or 2-ethoxybenzamide (mp
132-134 0C) containing water-soluble impurity and carbon.
(1) Dissolve the Solid: Place a 250-mL Erlenmeyer flask containing about 60-70
mL of water. Weigh 1-2 g of the unknown organic sample and put it in the
water while it is cold. Place the Erlenmeyer flask on a hot plate and allow the
water to boil. Constantly stir the solution with a stirring rod until all the
unknown solid dissolves. Record in your notebook the exact volume of water
you added.
(2) Filter the Insoluble Impurities: Using hot, gravity filtration, add about 5 mL
of hot solvent to the funnel containing the filter paper; this preheats the funnel
but is not a substitute for boiling the solvent in flask before doing the filtration.
(3) Crystallize the Compound: Allow the flask to cool to room temperature, a
process that may be hastened by first cooling in a beaker of cold tap water
before placing it in an ice-water bath.
(4) Isolate the Crystals: Collect the recrystallized solid on a Buchner funnel
attached to the filtration flask that must be clamped. Connect the filter directly
to the house vacuum line using a heavy-walled tubing provided(do not use
condensed hose as it will collapse under vacuum).
(5) Dry the Crystals: Place the top part of the Buchner funnel containing the
solid in a beaker so it won’t fall over when you open your locker and store it in
you locker of hood to dry. Do not cover the funnel or the beaker. During the
next lab period, transfer the crystals from the funnel to a clean dry sample
vial. Wash the vial with water and then with acetone, followed by drying on a
laboratory dryer or oven before putting the sample in it. Determine the weight
of pure sample solid in grams and percent recovery, which is defined as:
Percent recovery =
weight of pure sample, g/weight of impure sample, g x
100.
Determine the mp of the solid and identify the unknown using the mixed mp
technique, as described in part (b) below.
Melting Points: Read Zubrick, Chapter 12.
Experiment: Determine the melting points of:
(a) Your recrystallized unknown
(b) Your unknown mixed with benzamide (50:50)
(c) Your unknown mixed with 2-ethoxybenzamide (50:50)
Melting point will be determined using the MelTemp melting point apparatus
which will be demonstrated in the laboratory. On the basis of this mixed melting
data, identify your unknown.
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(1) Data sheets for both parts
Put the recrystallized sample in a properly labeled sample vial. Return any
unused unknown to your instructor
(2) Waste Disposal and Clean UP
Used capillary tubes-place in “used capillary tube” beaker on the bench. Place all
used filter paper in the trash-can. Put all solutions in the sink.
(3) Laboratory Report
This two-part investigative experiment is to be written up as a single laboratory
report-see Section H(a). The report will receive a single grade that will be
determined by the quality of the written report and to a lesser extent by the yield
and purity of the recrystallized solid. As a guide, see “Laboratory Report on
Recrystallization and Melting Point” in CHEM 307 Supplements.
3. DISTILLATION AND GAS CHROMATOGRAPHY
(a) Distillation: Read Zubrick Chapters 13, 17, 18(heating mantle), 19, 20.
Experiment:
Do experiment in Zubrick, chapter 20”Class 3: Fractional” This experiment will be
done in pairs. All equipment must be clean and dry. Each student must record
the data in his/her laboratory notebook. Each student will perform fractional
distillation on a 50-50 mixture of ethyl acetate and butyl acetate. Place a 35-mL
sample of this mixture in a 100 mL round bottom flask containing several boiling
chips. Use Rashing rings as the column packing. Place the thermometer so that
the top of the mercury bulb is just slightly below the bottom of the sidearm of the
distillation head. Collect three (3) 10-mL fractions in clean, dry large sample vials
clamped just below the take off adapter. Calibrate each sample vial by placing
10-mL of water in another vial and marking the 10-mL level of the three clean dry
vials with a marking pen. Label each vial to identify the fraction number A heating
mantle will be used for heating. Start with the VARIAC set at 90, When you start
to collect the 10-mL fractions increase the setting on the VARIAC to 125 for the
remainder of the distillation. Record the distillation data in your notebook in a
table with the following heading:
Fraction number
bp range
volume collected
Other observations: (1) Color of original mixture and color of each fraction must
be recorded in your notebook. (2) At the completion of the distillation, turn off
VARIAC , remove the heating mantle, and allow the apparatus to cool. Submit a
sample of each fraction for gas chromatographic analysis-see part(b) bellow. The
method of sample submission will be demonstrated. Tightly cap each of the
original vials and place them ina beaker to keep them from tipping over. Keep
them in your personal drawer until the gas chromatography results are returned
to you.
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Hand in: The data sheets from the distillation should be handed in.
Waste Disposal and Clean UP:
(1) Pot residue-place in “organic waste” bottle in the hood after determining the
volume remaining in the flask.
(2) Column packing-place in the “used column packing” beaker in the hood.
(3) Clean and put all glassware and equipment in proper locker. Clean and dry
your work area.
(b) Gas Chromatography: Read Zubrick Chapter 31.
Experiment
Cap each sample vial and shake each one to ensure complete mixing. Submit a
sample of each fraction obtained by each pair of students for analysis using autoinjection gas chromatography.
Analysis of gas chromatography
The GC data you will get back contains the GC traces for each fraction and a
copy of the GC of the standards. The standards are ethyl acetate and butyl
acetate so that the peaks in the GC traces for the three fractions can be
identified. The retention times are provided at the top of each peak and also in
the data summary at the bottom of the sheet. If an area given as 100e2 this
represents 100%.
Waste Disposal
1. After getting back the gas chromatographs, place the rest of each sample in
“organic waste” container in the hood
2. Wash sample vials and place them in your personal drawer.
Laboratory Report
Write one report covering fractional distillation and gas chromatography as an
investigative experiment-see Section H(a). For each pair of students performing
fractional distillation, one set of GCs of the three fractions and of the standards
will be provided. Each student must submit a report for this experiment and
each report must contain the GC traces for the three fractions and the
standards. One student may submit he original GC data and the other may
submit photocopies of it. In addition to the normal report format (Name, course
number, and section in the upper right hand corner, followed by Experiment Title
and References in the Center and the Introduction in few sentences) use the
following format for the rest of the report
Data: The data for fractional distillation and gas chromatography must be
presented in a table, per the following example. Scientific data routinely
presented in tables in the literature.
Fraction
acetate
Number
fraction
volume(mL)
bp or bp range Ethyl acetate
Retention time
Ethyl acetate
% in fraction
Butyl acetate
Retention time
Questions
Answer the following question by number, following the table of data.
Butyl
% in
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1. What is the purpose of fractionally distilling a mixture of two compounds
whose boiling points are fairly close, as is the case of ethyl acetate and butyl
acetate?
2. What is the purpose of performing chromatography on each fraction?
3. Ideally fraction 1 should contain what pure compound? Did it?
4. Ideally fraction 3 should have contained what pure substance? Did it?
5. Should fraction 2 contain only 1 compound? If not, what should it contain?
6. If fraction 1 and/or 3 were a mixture, what do you think may have caused it?
What might you do experimentally to get pure compounds in fraction 1 and 3?
7. What effects would the following changes in the experimental procedure have
on the separation of the mixture(improve it make it worse, have no effect?)
(a) Increase the temperature (VARIAC setting) at the beginning of the distillation.
(b) Use a fractional distillation column that was twice as long.
8. You start with 35 mL of a mixture of 25% ethyl acetate and 75%butyl acetate
and collect 10 mL fractions. Assuming perfect separation, what compound(s)
should be contained in (a) fraction a, (b) fraction 2 and (c) fraction 3?
9. Based on your data, what is the boiling point of ethyl acetate and butyl
acetate?
Attach the gc traces of each fraction and of the standard at the end of the
report.
3. PREPARATION OF CYCLOHEXENE (Preparative)
Read: “Preparation of Cyclohexene” in CHEM 307 Supplements; Zubrick
Chapter 15, McMurry, see 17.7
Experiment: “Preparation of cyclohexene” in CHEM 307 Supplements. Run
infrared soectrum of your cyclohexene product. The “IR Spectrum of
cyclohexanol” is in the CHEM 307 Supplements.
Hand In: Data sheets. Properly labeled the product after running its IR
spectrum. No product handed in -10 points from the final report.
Laboratory Report for Preparation of cyclohexene. See section H(b) in this
lab syllabus and “Preparative Experiments” in the CHEM 307 Supplements.
Include the mechanism for this reaction. In your Results and Conclusions, also
analyze the IR that you ran on your product and that of cyclohexanol and hand
both IR spectra in with the report.
4&5. Preparation of 1-Bromobutane and Infrared Spectroscopy
(a) Preparation of 1-Bromobutane(Preparative)
Read: McMurry, Secs. 10.7, 11.16. Zubrick, Chapters 15, 18,19, 20, 22.
“Preparation of 1-Bromobutane” in CHEM 307 Supplements. Omit mechanism.
Experiment: “Preparation of 1-Bromobutane” in CHEM 307 Supplements. Run
infrared soectrum of your final product.
Hand In: Data sheets. Properly labeled the product after running its IR spectrum.
No product handed in -10 points from the final report.
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Laboratory Report for Preparation of cyclohexene. See section H(b) in this
lab syllabus and “Preparative Experiments” Part II in the CHEM 307
Supplements. Omit the mechanism for the reaction.
(b) Infrared Spectroscopy (Investigative)
Read: Zubrick Chapter 33. McMurry, Secs. 12.5-12.9
Experiment:
1. 1-Bromobutane Run infrared spectrum of your 1-bromobutane
product from the experiment(a) above. The “IR Spectrum of 1–Butanol”
is in the CHEM 307 Supplements
2. Unknown Obtain the IR spectrum of the unknown liquid provided you.
On the basis of the IR spectrum, use the “List of Possible IR
Unknowns” in CHEM 307 Supplements to determine the structure of
the unknown.
Laboratory Report for Infrared Spectroscopy
See Section H(b) of this syllabus. Specific comments are provided here.
1. For the spectra of 1-butanol and your 1-bromobutane product, interpret
each by marking key absorption peaks on each spectrum and write
what causes each peak. Write a paragraph concerning the changes
that were observed in the spectra of the starting material and the
product, and state how the spectra showed that the reaction had in fact
occurred.
2. For the Unknown, mark key absorption peaks directly on the spectrum
and write what causes each peak. On the basis provide the structure of
the unknown from the “List of Possible IR Unknowns” in the CHEM 307
Supplements. Start by identifying structural features and functional
group(s) in the compound whose IR you have run. Each unknown will
contain at least two structural features and/or functional groups. Mark
directly on the key absorption peaks that provide information about
structural features and functional group(s). Table 3.1 (pages 70-71)
McMurry provides a table of the family names, examples and the
structure of commonly encountered functional groups. Limit your
consideration to the following. It may help you to write the functional
group structure by each name using Table 3.1
Aliphatic groups(hydrogens attached to sp3 hybridized carbon atoms)
Aromatic ring( aromatic hydrogens and carbon-carbon bonds associated
with ringsalcohol
Aldehyde
Ketones
Alkene( vinyl hydrogens and c=c stretching)
Alkynes (terminal hydrogen and c-c triple bond streching)
Amines ( 10, 20, and 30)
Carboxylic acid
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Esters
Nitrile
Nitro
Amides( 10, 20, and 30)
As a hint, eliminate compounds on the list that you know your unknown
can’t be; for example the absence of a peak due to –OH stretch allows
you to eliminate alcohols, carboxylic acids, and phenols.
3. Attach the three IR spectra to your report.
6. MOLECULAR MODELS (Investigative)
Read: McMurry, Secs. 3.2, 3.3. Chapters 4 and 9.
Experiment: “Directions for Molecular Model Experiment” in CHEM 307
Supplements. This experiment will be “in lab” practical concerning
stereochemistry of organic molecules. You may use any materials or books you
desire and may discuss it with other students and your instructor.
Hand In: the answer sheet at the conclusion of the experiment.
7. Compound Identification; Infrared Spectroscopy (IR), Proton
Magnetic Resonance Spectroscopy (PMR) and Mass Spectrometry
(MS) (Investigative)
The lecture and laboratory will be devoted to: (a) discussion of IR;
(b)discussion of MS; (c) discussion of PMR and (d) compound
identification using IF, PMR and MS.
Reading and Study Problems
IR Spectroscopy: McMurry Secs. 12.5-12.8. “Spectra Data”, “Sample IR
Spectra”, and “Structure Determination Problems Using IR Spectroscopy”
in CHEM307 Supplements.
PMR Spectroscopy: McMurry : Secs. 13.1-13.3 and secs. 13.8-13.13.
“Spectra Data”, “Sample PMR Spectra; Structure Determination Using IR,
MS and PMR Data” and “Structure Determination Problems using IR and
PMR Data” in CHEM 307 Supplements.
Mass Spectrometry: McMurry, Secs 12.1-12.4. “Sample Mass Spectra” in
CHEM 307 Supplements. Answers to these problems: “Answers to
Spectral Problems Sets” in CHEM 307 Supplements. Ignore any
references to CMR and CMR problems.
(a) Infrared Spectroscopy (IR)
The interpretation of IR spectra will be discussed for compounds
containing all commonly encountered functional groups. This technique
will be used (a) on the product obtained from dehydration of cyclohexanol,
(b) to identify the IR unknown [Expt. 4(b) and (c) in the compound
identification experiment (Expt. 6) described below.
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(b) Proton Magnetic Resonance (PMR)
The interpretation of PMR spectra will be discussed for compounds
containing some commonly encountered functional groups. This technique
will be used in the compound identification experiment, part (d) below.
(c) Mass Spectrometry (MS)
The interpretation of mass spectra will be discussed to learn how it may
be used to determine (1) the presence or absence of Cl or Br in a
compound and (2) the molecular weight of the compound. This technique
will be used in the compound identification experiment, part (d) below
(d) Compound Identification (Investigative)
This experiment combines IR, MS, and PMR to deduce the structure of an
unknown organic compound.
Experiment: You will be given a liquid unknown to identify using spectral
methods. Run an IR spectrum of your unknown. Analyze your IR spectrum
and identify important structural features by marking the appropriate peaks
on the spectrum. The unknown will be drawn from he following families of
compounds: alkanes and cycloalkanes, alkenes and cycloalkenes,
alkynes, alcohols, alkylhalides and aromatic compounds(aryl halides
and aromatic hydrocarbons) You will be provided a copy of the mass
spectrum and of the PMR of youar unknown. Analyze the mass spectrum
to determine the presence or absence of Br or Cl and to obtain the
molecular weight of the compound. Use the PMR spectrum as much as
possible to determine structural features of the unknown.
Complete and hand in the preliminary Report form that is attached to the
MS and PMR spectra provided for your unknown. Follow the directions on
the orm. Attached the IR, PMR and MS of your unknown. The corrected
Preliminary Report will be returned to you along with the percent (%)
composition by weight for the unknown.
Laboratory Report
Use the following format for this report. Please keep it brief and to the
point. Please do NOT include any information that is not relevant.
Name, Date Lab Section (in the upper right corner)
1. Introduction
2. Calculate empirical formula from the % composition and determine the
molecular formula from the empirical formula weight.
3. Interpret PMR spectrum. Your interpretation must account for the
chemical shift(indicate which hydrogens are responsible for which
peaks), the peak areas, and the splitting pattern. To calculate peak
areas, see “PMR Peak Area Calculation” in CHEM 307 Supplements.
4. Identify the unknown (Name and structure).
5. At the end of the report, attach graded Preliminary Report and
interpreted PMR, MS, and IR spectra.
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K. Study Guide for Laboratory Exams
The following is provided as study guide for the laboratory examination as
follows:
First Laboratory Exam: Parts 1-7 below (no spectroscopy)
Second Laboratory Exam: Parts 8-12 below
Review Pre-lab Exercises and Lab Reports
1.
General Comments You are not expected to remember weights or
volumes of various materials and reagents that you used in lab. The
emphasis will be on your understanding of the principles, concepts, and
techniques used in laboratory work.
2.
Equipment and Apparatus You should be able to identify all of the lab
equipment that were used in lab this semester. Review each equipment.
3.
Laboratory Safety, Equipment and Waste Disposal Review the
comments and reading assignments. See section B of this syllabus.
4.
Recrystallization and Melting Point Understand the concept of melting
points and effect of impurities on them Know the terms from the reading,
as for example: mixed mp, eutetic points, etc. Understand the use of
mixed mp and compound identificaion. For recrystallization, know:
purpose, experimental steps, and rationale of allowing crystals to form and
leave impurities behind.
5.
Distillation Understand the concept of fractional distillation. Knw
eqipment for fractional distillation. Know about azeotrope mixture.
6.
Gas Chromatography Know the general principles of method: how and
why it works. Know how to read and interpret GC chart—retention times,
% composition, and use of standards to identify compounds.
7.
Preparation of 1-Bromobutane
Know names and strucutres of
reactants. Know how to calculate limiting reagents, theoretical yield and
percent yield. Understand the purification method and why various steps
were done, use of drying agents, the apparatus that was used(including
reflux and simple distilation). Review the discussion and experimental
procedure in the handout.
8.
Infrared Spectroscopy Understand the use of IR. Tablesof IR absorption
values will be supplied for your use.
9.
PMR Know how to interpret PMR spectra and be able to account for
chemical shift, peak areas, and splitting patterns. Tables of PMR chemical
shifts will be provided for your use.
10.
MS
Know how MS work and how to interpret MS spectra for the
presence of Br and Cl: fragments whose masses are 2 mass units apart
with abundance of (a) 3:1 indicate presence of Cl or (b) 1:1 indicate
presence of Br. Know parent peaks , base peaks, and how to determine
molecular weight.
11.
PMR, IR, MS and Compound Identification Know how to derive
empirical formula from percent composition by weight. Know how to derive
molecular formula from empirical formula. Know how to combine spectral
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12.
information (IR, MS, and PMR) to get the structure of an unknown
compound.
Preparation of Cyclohexene Know how to determine limiting reagent
and theoretical yield and % yield. Understand purification scheme and
procedure. Why various steps were performed ,use of drying agents, etc.
Know why fractional distillation apparatus was used for the dehydration
reaction. Review the discussion and experimental procedure in the
handout.