CHM 325 Organic I
This is an introductory course that introduces some techniques (which in our new program has some of
these moved to the new techniques course) and then moves onto reaction chemistry by functional group. IR
spectroscopy is introduced and all the reactions require the student to also run their own IR’s, TLC’s and
mp/bp’s
Experiment #1 An Introduction to Thin-Layer Chromatography (TLC)
Shows the student how to stretch pipettes into capillaries and how to run qualitative TLC’s
Experiment #2 Melting Point and Boiling Point
Students learn how to use Thiele tubes for mp’s and also two methods for bp determinations
Experiment #3 Recrystallization
The complete process of recrystallization of benzoic acid is illustrated.
Experiment #4 Simple Distillation
A simple distillation is setup and run for low boiling liquids such as methanol
Experiment #5 Fractional Distillation
The fractioning column is used to help separate two liquids such as methanol and water.
Experiment #6 Introduction to the Separatory Funnel and Extraction with Solvent
Benzil and benzoic acid are separated using the separatory funnel.
Experiment #7 Bromination of an Alkene
Br
1.1 equiv. Br2 in CH2Cl2
Br
Experiment #8 Hydration (Oxymercuration) of an Alkene
OH
1. ( 0.9 eq) Hg(OAc)2 in 1:1 H2O/THF
2. (0.5 eq) NaBH4 (~ 0.5M sol'n in 3M NaOH)
Experiment #9 Formation of an Alkyne
Br
KOH (xs), Triethylene glycol
Br
Experiment #10 Hydration of an Alkyne
O
(0.2 eq) HgSO4, methanol/H2O,
few drops H2SO4, reflux
Experiment #11 Aromatic Nitration
Cl
Cl
Cl
HNO3 / H2SO4 in xs
NO2
+
NO2
Experiment #12 Reduction of a Nitro Group
Cl
Cl
+
2. -OH
NO2
Cl
Cl
1. Sn (2 eq), HCl (conc.)
NO2
NH2
+
NH2
Experiment #13 Friedel-Crafts Acetylation
O
O
(1.2 eq) Acetic anhydride,
(2.0 eq) AlCl3
O
Experiment #14 Column Chromatography
Column chromatography is introduced to the student by using silica gel for the packing and organic
solvent as eluent. The crude reaction mixture from experiement #13 can be used or something like
benzaldehyde/benzoic acid mixture.
CHM 427 Organic II
Organic II picks up where I left off both in terms of the chemistry of various functional groups, but also
by introducing 1H and 13C NMR spectroscopy. As part of standard protocol for handing in their lab reports,
students must:
- provide a TLC strip that includes starting material, their product and pure compound where applicable
- provide an IR spectra of their starting material and reaction product
- provide an analysis of the 1H and 13C NMR spectra provided to them. (It is a real spectra of one of the students
reaction products)
- provide a m.p or b.p (Siwoloboff method) of their product as required.
Experiment #1 Separation of a Basic and Neutral Compound
3-nitroaniline is separated from menthol through the use of the separatory funnel.
Experiment #2 Preparation of t-Butyl Chloride via an Sn1 Reaction
t-butyl chloride is prepared and isolated from t-butyl alcohol.
OH
xs conc. HCl
Cl
Experiment #3 Preparation of Menthyl Chloride
Conversion of menthol to menthyl chloride
SOCl2
OH
Cl
Experiment #4 Formation of Cyclohexene by an E1 Mechanism
Synthesis of cyclohexene by elimination of water from cyclohexanol
OH
H2SO4 or H3PO4
Experiment #5 Jone's Oxidation of Cyclohexanol
Cyclohexanone is made by oxidizing cyclohexanol with Jone’s reagent.
OH
O
CrO3/H+/Acetone
Experiment #6 Preparation of Triphenylmethanol by Grignard
Br
1. Mg, in ether
Ph
OH
O
2.
Ph
Ph
Ph
Ph
+
3. H
Experiment #7 Preparation of Trityl methyl ether
The most stable cation known is made from triphenylmethanol then converted to the corresponding
methyl ether.
Ph
OH
Ph
Ph
1. H+
2. methanol
Ph
Ph
OMe
Ph
Experiment #8 Preparation of Isobutyryl Chloride
The acid chloride of isobutyric acid (smell of rancid butter!) is made using thionyl chloride.
O
O
OH
SOCl2
Cl
Experiment #9 Preparation of Isobutyramide
Treatment of the previous week’s product is converted to the corresponding amide.
O
O
NH3
Cl
NH2
Experiment #10 Preparation of Aspirin
A classic experiment. Making aspirin.
O
OH
O
OH
OH
acetic anhydride
O
O
Experiment #11 Reduction of a Carboxylic Acid
Reduction of a carboxylic acid using a stronger reducing agent (LAH) than sodium borohydride.
O
OH
OH
LiAlH4 in THF
reflux
Experiment #12 and #13 (Two Weeks) Identification of an Unknown Alcohol
Object: To identify an unknown alcohol through some physical properties, tests and its ethyl ester from a list
of possibilities. See lab manual for details.
CHM 527 Organic III
This adds some HPLC but more importantly puts all the burden on the student. They have the manual
and are essentially told to provide the indicated products in quality fashion by the end of the semester in any
order they wish. For each experiment the student must provide:
- TLC strip of quality
- IR and UV spectrum of their starting material and product
- HPLC or GC chromatogram
- 1H and 13C NMR and MS spectral analysis of starting materials and product
- sample of high quality (usually through recrystallization) for grading
- mp and bp as required
Experiment #1 Acetylation of Glycine
O
O
acetic anhydride
H2N
N
OH
OH
O
Experiment #2 Condensation of Acetylglycine with an Aldehyde
O
O
N
OH
+
acetic anhydride
H
MeO
O
sodium acetate
O
N
MeO
O
CH3
Experiment #3 Condensation of Benzaldehyde and Acetophenone
O
O
O
CH3
+
H
NaOH
EtOH
Experiment #4 Diazonium Coupling
N Cl-
NH2
OH
N
HCl
N
N
NaNO2
HO
Experiment #5 Benzoin Condensation
O
2
NH2
H
Cl
N
N
H3C
O
CH3
N
S
H
OH
OH
Thiamine HCl
(catalytic amount
Experiment #6 Oxidation of Benzoin to make Benzil
O
O
HNO3
acetic acid
OH
O
Experiment #7 Synthesis of Dilantin
O
OH
O
O
N
KOH
+
N
Ph
H2N
NH2
EtOH/H2O
Ph
O
Experiment #8 Michael Reaction
O
O
EtO
+
O
EtO
O
Ph
O
Ph
CH3
Experiment #9 Reaction From Literature
You will each be given one of three compounds. You must go and find a reaction to try on this
compound from some literary source. You must make sure that the stockroom has the necessary reagents. I
would suggest searching through Jerry March’s Text (which I have a copy of, but so does the library) by
functionality or type of reaction. He then lists some journal references which can be obtained at the University
of Windsor library. Look up a number of them to photocopy so that you don’t have to go back if the one you
chose has reagents we don’t carry. Then submit your proposed reaction to the instructor for approval. Special
allowances for lab time can be made (stirring overnite for example) if you really wish to try something. This
reaction must be approved by the 7 th week of class.
Note: You must provide a photocopy of journal prep.
Experiment #10 The Unknown Compound
Giving a student an unknown (pure or essentially pure) organic compound and asking them to figure out
what it is, has been a right of passage for many years. Traditionally, the possibilities were narrowed down by
way of a list that students could choose from followed by matching the melting points of their derivatives.
Today, that is unrealistic (although still good practice in the lab) because with spectroscopic methods and a
much larger workplace containing many compounds, the “What is it?” question can have many possibilities yet
still be answered. So, the student will be given an unknown compound and must perform a list of required tasks
and finally propose what their compound is backed up by some logic. Once identified, one reaction must be
performed on it similar in approach to experiment 8. That is, the student will find a reaction to try on their
unknown.
The student must obtain:
1.
2.
3.
4.
5.
6.
mp or bp
TLC in an attempt to check purity. (May not always be possible)
Classification by solubility
UV spectrum
IR spectrum
1
H and 13C spectra