CHM456 ORGANIC CHEMISTRY I
LIST OF PRACTICALS
1.
2.
3.
4.
5.
6.
7.
8.
9.
Briefing on laboratory work and safety
Acid-base extraction
Preparation of 4-methylcyclohexene from dehydration of 4-methylcyclohexanol
Preparation of 1-bromobutane from 1-butanol
Oxidation of d,l-menthol to menthone with PCC
Preparation of acetylsalicyclic acid
Thin Layer Chromatography (TLC)
Nitration of methylbenzoate (electrophilic aromatic substitution)
Friedel-Craft’s acylation
Experiment 1 (will be combined with Experiment 2)
Briefing on laboratory work and safety
References
Bell et al., “Organic Chemistry Laboratory with qualitative analysis”, Thomson
Brooks/Cole, 2000, page 1-13.
Chemicals
None
Glassware
None
Activities
1.
Draw a sketch of the organic chemistry laboratory and the hallway outside, in
which you clearly show the location of each of the following:
a) The safety shower
b) All fire extinguishers
c) All fume hoods
d) Eyewash fountains
e) Your desk
2.
Use the most recent Handbook of Chemistry and Physics (CRC Handbook) to
find the following data:
a) The refractive indices of acetone and hexane
b) The boiling points of 1-propanol and 2-propanol
c) The melting points of acetanilide and benzoic acid
d) The densities of ethyl acetate and butyl acetate
3.
Are organic vapors heavier or lighter than air?
4.
Draw a simple reflux apparatus and identify each piece of glassware. Draw the
distillation apparatus.
5.
Calculate the percentage yield for diethyl succinate (MW 174) if 10 g of succinic
acid (MW 118) and 100 ml of ethanol (MW 46, d 0.79 g/mL) were used to
produce 8.7 g of diethyl succinate.
(CH2COOH)2
+
2CH3CH2OH
succinic acid
+
H
ethanol
(CH2CO2CH2CH3)2
+
2H2O
diethyl succinate
Experiment 2 (will be combined with Experiment 1)
Acid-base extraction
References
“CHM523 Organic Chemistry Laboratory Manual” prepared by Yazan Zakaria (referring
to “Introduction to Organic Laboratory Techniques”, Pavia, Lampman, Kriz and Engel,
2011), page 458.
Chemicals
Triphenylmethanol or 1,2,4,5-tetrachlorobenzene (as unknown)
Diethylether
1.0M HCl
Sat. sodium chloride, NaCl (brine solution)
Anhydrous sodium sulfate, Na2SO4
Glassware
No special glassware required
Experiment 3
Preparation of 4-methylcyclohexene from dehydration of 4-methylcyclohexanol
References
“CHM523 Organic Chemistry Laboratory Manual” prepared by Yazan Zakaria (referring
to “Introduction to Organic Laboratory Techniques”, Pavia, Lampman, Kriz and Engel,
2011), page 561.
Chemicals
4-methylcyclohexanol
85% phosphoric acid H3PO4
Conc.sulfuric acid, H2SO4
Sat. sodium chloride, NaCl (brine solution)
Anhydrous sodium sulfate, Na2SO4
Bromine test reagent
Potassium permanganate test reagent
Glassware
No special glassware required
Experiment 4
Preparation of 1-bromobutane from 1-butanol
References
“CHM523 Organic Chemistry Laboratory Manual” prepared by Yazan Zakaria (referring
to “Introduction to Organic Laboratory Techniques”, Pavia, Lampman, Kriz and Engel,
2011), page 557.
Chemicals
Sodium bromide, NaBr
1-butanol
Distilled water
Conc. sulfuric acid, H2SO4
9M sulfuric acid, H2SO4
Sat. sodium bicarbonate, NaHCO3
Anhydrous calcium chloride, CaCl2
Bromine test reagent
Potassium permanganate test reagent
Glassware
No special glassware required
Experiment 5 (will not be conducted in semester July-Nov 2010; no chemicals)
Oxidation of d,l-menthol to menthone with PCC
References
(Journal)
Chemicals
Glassware
No special glassware required
Experiment 6
Preparation of acetylsalicyclic acid
References
Pavia et al.,“Introduction to Organic Laboratory Techniques”, Thomson Brooks/Cole,
2011, page 481.
Chemicals
Salicyclic acid
Acetic anhydride
Conc. sulfuric acid, H2SO4
1% ferric chloride solution (Ferric chloride test reagent)
Ethyl acetate (for recrystallization)
Glassware
No special glassware required
Experiment 7
Thin Layer Chromatography (TLC): TLC analysis of analgesic drugs
References
“CHM523 Organic Chemistry Laboratory Manual” prepared by Yazan Zakaria (referring
to “Introduction to Organic Laboratory Techniques”, Pavia, Lampman, Kriz and Engel,
2011), page 488.
Chemicals
Aspirin, caffeine and acetaminophen as reference standards
An analgesic tablet (eg. Panadol or Uphamol)
0.5% glacial acetic acetic acid in ethyl acetate
Ethanol
Dichloromethane
Glassware
Capillary tubes
Development chamber
Silica gel 60 F-254 chromatographic plates
Experiment 8
Nitration of methylbenzoate (electrophilic aromatic substitution)
References
“CHM523 Organic Chemistry Laboratory Manual” prepared by Yazan Zakaria (referring
to “Introduction to Organic Laboratory Techniques”, Pavia, Lampman, Kriz and Engel,
2011), page 698.
Chemicals
Methyl benzoate
Conc. sulfuric acid, H2SO4
Conc. nitric acid, HNO3
Glassware
No special glassware required
Experiment 9 (will not be conducted in semester July-Nov 2010; no glassware)
Friedel-Craft’s acylation
References
Pavia et al.,“Introduction to Organic Laboratory Techniques”, Thomson Brooks/Cole,
2011, page 531.
Chemicals
Toluene
Acetyl chloride
Aluminium chloride, anhydrous
CaCl2 drying agent for chemical reactions
Anhydrous sodium sulfate, Na2SO4
Dichloromethane, DCM
Sat. sodium bicarbonate, NaHCO3
Glassware
250ml three-neck round bottom flask (middle neck 24/29, side necks 19/24)
500ml three-neck round bottom flask (middle neck 24/29, side necks 19/24)
Drying tube
Aspirator trap
125ml separatory funnel with quick fit dispenser (19/24)
250ml separatory funnel with quick fit dispenser (19/24)
Glass adapter 19/24 to 24/29
Glass adapter 24/29 to 19/24
CHEMICALS REQUIRED FOR CHM456 LABORATORY
0.5% glacial acetic acetic acid in ethyl acetate
1% ferric chloride solution (Ferric chloride test reagent)
1.0M HCl
1-butanol
4-methylcyclohexanol
85% phosphoric acid H3PO4
9M sulfuric acid, H2SO4
Acetic anhydride
Acetyl chloride
Aluminium chloride, anhydrous
Anhydrous calcium chloride, CaCl2
Anhydrous sodium sulfate, Na2SO4
Aspirin, caffeine, acetaminophen, Panadol or Uphamol
Bromine test reagent
CaCl2 drying agent for chemical reactions
Conc. nitric acid, HNO3
Conc. sulfuric acid, H2SO4
Dichloromethane, DCM
Diethylether
Distilled water
Ethanol
Ethyl acetate (for recrystallization)
Methyl benzoate
Potassium permanganate test reagent
Salicyclic acid
Sat. NaCl (brine solution)
Sat. sodium bicarbonate, NaHCO3
Sodium bromide, NaBr
Toluene
Triphenylmethanol or 1,2,4,5-tetrachlorobenzene (as unknown)
SPECIFIC GLASSWARE FOR CHM456 LABORATORY
250ml three-neck round bottom flask (middle neck 24/29, side necks 19/24)
500ml three-neck round bottom flask (middle neck 24/29, side necks 19/24)
Drying tube
Aspirator trap
125ml separatory funnel with quick fit dispenser (19/24)
250ml separatory funnel with quick fit dispenser (19/24)
Glass adapter 19/24 to 24/29
Glass adapter 24/29 to 19/24