Академический Документы
Профессиональный Документы
Культура Документы
Date:
Partners
Katheryn Soto
N/A
11/24/15
Drawer No.
Course / Section
#21
CHEM
315/204
Purpose:
The purpose of this experiment is to analyze an unknown organic compound through the use of physical
and chemical tests to identify unknown halides, hydrocarbons and alcohols, measurement of its refractive
index, and analysis of its IR spectrum.
Experiment:
Date:
Partners
Katheryn Soto
N/A
11/24/15
Drawer No.
Course / Section
#21
CHEM
315/204
Approach:
Determine the rough boiling point of and purify the unknown via simple distillation. Describe the
physical characteristics of the unknown sample. Determine the relative solubility of the unknown
compound in H2O and H2SO4. Determine the density of the unknown compound relative to H2O.
Perform the Beilstein test to check for the presence of halides. Perform the Silver nitrate in Ethanol
test and Sodium Iodide in Acetone test to check for the presence of Alkyl and Aryl Halides. Perform
Bromine in Methylene Chloride and Potassium Permanganate tests to check for the presence of
unsaturated hydrocarbons. Perform Ignition test to check for the presence of aromatic ring
structures. Perform Acetyl Chloride, Lucas, and Chromic acid tests to determine if alcohol is present
in the compound. Determine the refractive index of the unknown compound using the Abbe
Refractometer. Calculate the adjusted refractive index using the temperature correction factor.
Obtain and analyze IR and mass spectra for the unknown compound.
References
Text
Pavia, D.L., Lampman, G.M., Kriz, G.S., Engel, .G.R., 2011, Introduction to Organic Laboratory
Techniques, A Small Scale Approach, GMU Edition, Chem 315/318, Cengage Learning: pp.446461; pp. 464-468; pp. 483-487
Slayden, S., Stalick, W., Roth, R, 2014, Organic Chemistry Laboratory Manual, 2nd Edition:
Pearson Custom Publishing: pp. 71-75
Web Site URL
Dr Schornicks Website: http:/mason.gmu.edu/~jschorni/organicqualanalysisB&W
Unknown or Synthesized Compound:
1-Propanol (Propyl alcohol), CAS No. 71-23-8, CRC Handbook of Chemistry & Physics, 84th
Edition, Lide, D.R., Editor-in-chief, 2003-2004, CRC Press, #9166, p. 3-466.
Experiment:
Date:
11/24/15
Name
Partners
Katheryn Soto
N/A
Proc # 1
Physical Properties
Materials
Equipment
Unknown
organic compound
(QA-69)
Equation Setup:
Course / Section
#21
CHEM
315/204
Results
Desc:
Drawer No.
Physical Characteristics
Physical State Liquid
Color
Colorless
Odor
Strong, alcohol-like
Experiment:
Date:
11/24/15
Name
Partners
Katheryn Soto
N/A
Proc # 2
Simple Distillation
Materials
Unknown
Organic Compound
Ice
Teflon boiling
chip
Results
Equipment
Simple
distillation
apparatus
Condenser
Distillation
head
Thermomet
er with adapter
25mL
distillation flask
25mL
receiving flask
Hot plate
Aluminum
plate
Sand bath
Aluminum
foil
Desc:
Drawer No.
Course / Section
#21
CHEM
315/204
Unk No. QA-69
Simple Distillation
Compound
B.P (oC)
Unknown QA-69
97-100oC
Observations:
Distillate began to form and drip into
Experiment:
Date:
11/24/15
Name
Partners
Katheryn Soto
N/A
Proc # 3
Solubility/Density
Unknown
organic compound
(QA-69)
Desc:
Equipment
2 Test tubes
Graduated
cylinder
Dropper
Equation Setup:
Course / Section
#21
CHEM
315/204
Results
Materials
Drawer No.
Compound
Unknown
Solubility/Density
Sol. H2O Sol. H2SO4
Density
Soluble
Soluble
Suspended
Observations:
The compound was soluble in H2O
Experiment:
Date:
11/24/15
Name
Partners
Katheryn Soto
N/A
Proc # 4
Refractive index
Unknown
organic compound
Tissue
Alcohol
Dropper
Equipment
Abbe
refractometer (
0.0002)
Desc:
Course / Section
#21
CHEM
315/204
Results
Materials
Drawer No.
Unk No.
1.3838
1.3840
1.3839
QA-69
Experiment:
Date:
11/24/15
Name
Partners
Katheryn Soto
N/A
Proc # 5
Equipment
Calculator
Desc:
Drawer No.
Course / Section
#21
CHEM
315/204
Results
Room temp = 22.oC
Unknown
ND20 = NDRm Temp + (Room Temp - 20)* 0.00045
ND20 = 1.3839 + (22-20) * 0.00045
ND20 = 1.3848
Experiment:
Date:
11/24/15
Name
Partners
Katheryn Soto
N/A
Proc #6
IR Spectroscopy
Materials
Drawer No.
Course / Section
#21
CHEM
315/204
Results
Equipment
Unknown
IR
Organic Compound
Spectrometer
(QA-69)
2 NaCl plates
(salt plate
Acetone
KBR (potassium
bromide) pellet
Chemwipe
Desc:
IR Spectral Analysis:
Strong broad OH stretch 3100-3400cm-1
Experiment:
Date:
11/24/15
Name
Partners
Katheryn Soto
N/A
Proc # 7
Beilstein Test
Unknown
organic compound
(QA-69)
2-Chlorobutane
Equipment
Copper
wire loop
Bunsen
burner
Desc:
Allow to cool.
Record observations
Equation Setup:
Course / Section
#21
CHEM
315/204
Results
Materials
Drawer No.
Beilstein Test
Compound
2-Chlorobutane
Unknown QA-69
Result
+
-
Observations:
2-Chlorobutane produced a green
Experiment:
Date:
11/24/15
Name
Partners
Katheryn Soto
N/A
Proc # 8
2 drops
Unknown Organic
Compound (QA-69)
2 mL 2% AgNO3
in C2H6O
2 drops 1
Chlorobutane
2 drops 2
Chlorobutane
2 drops T-Butyl
Chloride
2 drops
Chlorobenzene
Desc:
Equipment
Graduated
cylinder
Test tube
Test tube
rack
Dropper
2 Hotplates
2 250mL
beakers (water
baths)
2
thermometers
Record observations
Drawer No.
Course / Section
#21
CHEM
315/204
Results
Structure
Allyl, Benzyl, 3o Halide
1o and 2o Alkyl Halides
Aromatic, Vinyl
Result
White precipitate at
room temp (most stable
carbocation)
Cloudy at 100oC
Unreactive (least
stable)
100oC
+
+
+
-
Observations:
Both 1-Chlorobutane and 2 remained
Experiment:
Date:
11/24/15
Name
Partners
Katheryn Soto
N/A
Proc # 9
8 drops
Unknown Organic
Compound (QA-69)
2mL 15% NaI in
C3H6O
8 drops 1
Chlorobutane
8 drops 2
Chlorobutane
8 drops T-Butyl
Chloride
8 drops
Chlorobenzene
Desc:
Equipment
Test tubes
Dropper
Graduated
cylinder
Hot plate
Water bath
Record observations.
Drawer No.
Course / Section
#21
CHEM
315/204
Results
Structure
1o Alkyl Halide
2o and 3o Alkyl Halides
Allyl, Benzyl and Aryl
Result
Immediate white
precipitate at room
temp.
Cloudy white when
heated to 50oC and
cooled
Unreactive
+
-
50oC (and
cooled)
+
+
+
-
Observations:
1-Chlorobutane formed a white
Experiment:
Date:
11/24/15
Name
Partners
Katheryn Soto
N/A
Proc # 10
Materials
Equipment
4 drops
Test tube
Unknown Organic
Graduated
Compound (QA-69)
cylinder
1mL
2%
Br
in
2
Dropper
CH2Cl2
4 drops
Cyclohexane
4 drops
Cyclohexene
4 drops Toluene
Desc:
Addition reaction of Br2 to determine
aromatic compounds.
In a test tube, add 4 drops of unknown in
1mL of CH2Cl2
Add 2% Br2 in CH2Cl2 drop by drop and
Equation Setup:
Drawer No.
Course / Section
#21
CHEM
315/204
Results
Positive = Soln. decolorized after addition of 5 drops
of 2% Br2 in CH2Cl2
Negative = HBr is evolved (substitution rxn occurs
instead of addition due to no double or triple bonds
present)
Br2 in CH2Cl2 Test
Compound
Result
Cyclohexane
Cyclohexene
+
Toluene
+
Unknown QA-69
Observations:
When Br2 was added Cyclohexane
Experiment:
Date:
11/24/15
Name
Partners
Katheryn Soto
N/A
Proc # 11
Materials
Course / Section
#21
CHEM
315/204
Results
Equipment
2 drops
Test tube
Unknown Organic
Dropper
Compound (QA-69)
1% KMnO4 (aq)
Desc:
Oxidation reaction to test for double and
triple bonds.
Can react with other easily oxidized
compounds.
Add 2 drops in 2mL of one of the
Record observations
Equation Setup:
Drawer No.
Bayer Test
Compound
Cyclohexane
Cyclohexene
Toluene
Unknown QA-69
Result
+
+
+
Observations:
When KMnO4 was added Cyclohexane
a brown precipitate
Unknown QA-69 produced a brown
precipitate
Experiment:
Date:
11/24/15
Name
Partners
Katheryn Soto
N/A
Proc #12
Ignition Test
Materials
Course / Section
#21
CHEM
315/204
Results
Equipment
Bunsen
Unknown
burner
Organic Compound
(QA-69)
Spatula
Desc:
Tests for =C-H bonds in Aromatic rings
metal spatula.
Under the hood, place the spatula in the
Equation Setup:
Drawer No.
Ignition Test
Compound
Toluene
Unknown QA-69
Result
+
-
Observations:
Toluene produced a sooty black flame
Experiment:
Date:
11/24/15
Name
Partners
Katheryn Soto
N/A
Proc # 13
Materials
Course / Section
#21
CHEM
315/204
Results
Equipment
15 drops
Test tube
CH3COCl
Dropper
0.5mL Unknown
Graduated
Organic Compound
cylinder
0.5mL 1
Butanol
0.5mL 2
Propanol
0.5mL T-Amyl
alcohol
H2O
Desc:
Add 10-15 drops of CH3COCl to 0.5mL
Equation Setup:
Drawer No.
CH3COCl Test
Compound
1-Butanol
2-Propanol
T-Amyl alcohol
Unknown QA-69
Result
+
+
+
+
Observations:
1-Butanol, 2-Propanol, and T-Amyl
Experiment:
Date:
Partners
Katheryn Soto
N/A
Proc #
14
11/24/15
Drawer No.
Course / Section
#21
CHEM
315/204
Results
Equipment
2mL Lucas
Test tube
Lucas Test
reagent (Conc. HCl
Dropper
Compound
Immediate
Delayed/Heated
and Anhydrous
Graduated
1-Butanol
ZnCl2+)
cylinder
2-Propanol
+
4 drops
T-Amyl alcohol
+
+
Unknown Organic
Unknown QA-69
Compound (QA-69)
4 drops 1
Observations:
Butanol
When added to Lucas reagent, 1-Butanol
4 drops 2
remained clear both immediately and when
Propanol
heated.
4
drops
T
2-Propanol became cloudy several minutes
Amyl alcohol
after being added to the Lucas reagent
Desc:
T-Amyl alcohol became cloudy immediately
o
o
o
when added to the Lucas reagent
Test for 1 , 2 , and 3 alcohols. (liquid
precipitate
immediately or after a period of time or
Add 4 drops of liquid sample to 2mL of
Record observations.
Equation Setup:
Experiment:
Date:
11/24/15
Name
Partners
Katheryn Soto
N/A
Course / Section
#21
CHEM
315/204
Results
Equipment
1 drop
Test tube
Unknown Organic
Electronic
Liquid Compound
balance
(QA-69)
Graduated
1 drop Known
cylinder
Alcohol
1 drop Cr+6
1mL Acetone
1 drop 1
Butanol
1 drop 2
Propanol
1 drop T-Amyl
alcohol
Desc:
Redox reaction to detect 1oand 2o
Alcohols.
In 1mL acetone, dissolve 1drop of liquid
Record observations.
Setup:
Drawer No.
Cr+6 Test
Compound
1-Butanol
2-Propanol
T-Amyl alcohol
Unknown QA-69
Result
+
+
+
Observations:
Both 1-Butanol and 2-Propanol produced
Experiment:
Date:
Partners
Katheryn Soto
N/A
11/24/15
Drawer No.
Course / Section
#21
CHEM
315/204
Summary of Results:
Unknown QA-69 was a colorless liquid with a strong alcohol-like odor. The boiling point for QA-69
was 97-100oC. QA-69 was soluble in H2O but separated slightly and was suspended upon settling. QA69 was soluble in H2SO4 and produced a slight color change from clear to brown. The refractive index
for QA-69 was 1.3839. The adjusted refractive index for QA-69 was 1.3848. The IR spectrum for the
compound showed the following principal absorptions: Strong broad OH stretch 3100-3400cm -1,
saturated Aliphatic CH stretch <3000cm-1, and a strong CO stretch absorption at 1050-1150cm-1. The
Beilstein test for QA-69 was negative (did not produce a green flame when heated). The AgNO3 in
C2H6O and NaI in C3H6O tests for halides were unreactive. The ignition test with QA-69 was negative
(no sooty flame was produced). The Br2 in CH2Cl2 and Baeyer (KMnO4) tests for unsaturation were
unreactive. The unknown evolved heat when tested with acetyl chloride (positive). The Lucas test for
QA-69 did not produce a cloudy precipitate under immediate room temperature conditions or delayed
heated conditions. The Chromic acid test was positive, and produced an orange to blue/green color
change. The mass spectrum for the compound indicates a single M+ peak of 60.
Experiment:
Date:
Partners
Katheryn Soto
N/A
11/24/15
Drawer No.
Course / Section
#21
CHEM
315/204
compound has electrons that can react with a strong acid, suggesting the compound might be
an alkene, alkyne or aromatic alcohol (if soluble, and is most likely not an alkane or an alkyl
halide). The Beilstein test for QA-69 was negative, as no green color was detected in the flame,
indicating no halogens are present. Because no halogens were detected by the Beilstein test, the
results for AgNO3 in C2H6O and NaI in C3H6O halide tests were not applicable. The ignition test
for QA-69 negative, as the compound burned cleanly and did not produce a sooty flame,
indicating that it is likely that the compound contains saturated hydrocarbons. Because the
ignition test did not detect any unsaturated hydrocarbons, the results of the bromine and
KMnO4 tests for alkenes and alkynes were not applicable. The acetyl chloride test evolved heat
and was positive, indicating that the unknown is an alcohol. In the Lucas test, the unknown
did not produce a cloudy precipitate when initially added to the Lucas reagent, or when heated,
indicating that the compound is likely a primary alcohol and less likely a secondary alcohol.
The chromic acid solution turned from orange to blue green in the presence of QA-69,
indicating an oxidizable alcohol, supporting results of the Lucas test that the unknown is most
likely a primary alcohol. The boiling point determine during simple distillation of 97-100oC
most closely matches that of the primary alcohol 1- propanol.
The IR of unknown showed a strong broad OH stretch from 3100-3400cm-1, saturated Aliphatic CH
stretch <3000cm-1 indicating no double bonds are present, and a strong CO stretch absorption at 10501150cm-1 supporting identification of the compound as an alcohol. The mass spectrum for the
compound indicates a single M+ peak, suggesting that the compound does not contain the
halides Cl or Br. The primary alcohol that most closely matches this molecular weight and
contains fewer than 5 carbons is 1-propanol. The IR and mass spectra thus supports my
preliminary identification based on qualitative tests.
Experiment:
Date:
Partners
Katheryn Soto
N/A
11/24/15
Drawer No.
Course / Section
#21
CHEM
315/204
QA-69
CAS No.
71-23-8
Name (IUPAC)
1-propanol
Propyl alcohol
Synonyms
Melting Point
(oC)
Lit -124.39oC
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Boiling Point
(oC)
Lit 97.04oC
Exp 95oC
Lit
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Solubility
(Rel to Water)
Lit
Exp
Lit
Exp
Lit
Exp
Density
Rel to Water
Lit 0.799725g/cm-3
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Molecular
Formula
Structural
Formula
C3H8O