Makenna Good

Chemistry 222, Spring 2023

Dr. Easter
02/16/2023

Lab 1 Report: Qualitative Organic Analysis

“Unknown G”

Purpose-
The purpose of this lab was to identify and characterize the structure and functional groups of a
given unknown liquid using qualitative analysis techniques, and to confirm those findings
through the creation of a solid derivative.

Table of Reagents and Products-

Name Structure Molecular Molecular Density g/mL mmol mp/bp Hazards

Formula Weight (g/ml) used used °C @
(g/mol) lit
Water H2O 18.01 .999 As As mp: 0 N/A
needed needed
bp: 100
Acetone C3H6O 58.08 .784 As As mp: -95 Irritant
needed needed
bp: 56
Sodium Hydroxide NaOH 39.997 2.13 1.5 mp: Irritant
318.4 Can burn
skin
bp: 390
Sodium Bicarbonate NaHCO3 84.01 2.16 .5 mp: Irritant
>300

bp: 851
Hydrochloric Acid HCl 36.458 1.18 As mp: Corrosive
needed -114.2

bp:
85.05
 Makenna Good
Chemistry 222, Spring 2023
Dr. Easter
02/16/2023
Chromic Acid H2CrO4 118.01 1.2 1 drop mp: Corrosive
197 Irritant

bp: 250

Sulfuric Acid H2SO4 98.079 1.83 1 drop mp: 10 Corrosive

bp: 337
Zinc Chloride ZnCl2 136.286 2.91 1 mp: Irritant
290 Toxic

bp: 732
Alkyl Chloride C4H9Cl 176.73 .868 N/A mp: -34 Flammabl
e
bp: 223 Liquid
Explosive
2,4-dinitrobenzoate C6H6N4O4 198.14 1.7 3 mp: Burns
198- skin
202 Irritant

bp:
378.6
3,5-dinitrobenzoate C7H3N2O6 211.11 1.295 N/A mp: 94- Irritant
95

bp:
395.5
Benzamide C7H7NO 121.14 1.64 N/A mp: Corrosive
127- Irritant
130

bp: 288
Thionyl Chloride SOCl2 118.97 1.64 1 mp: Corrosive
Irritant
bp:
 Makenna Good
Chemistry 222, Spring 2023
Dr. Easter
02/16/2023
Anhydrous Calcium CaCl2 110.98 2.15 As As mp: - Can burn
Chloride needed needed skin
bp:
1935
Toluene C7H8 92.14 .865 5 mp: -95 Irritant

bp:
110.6

Benzyl Chloride C7H7Cl 126.58 1.1 N/A N/A mp: -39 Carcinoge
n
bp: 179 Mutagen
Ethanol C2H6OH 46.068 .789 As As mp: Irritant
needed needed -114.1

bp:
78.37
3,5-dinitrobenzoyl C7H3ClN2O 230.56 1.8836 .80 mp: 69- Irritant
chloride 5 69

bp: 196
Phenol C6H5O 94.11 1.07 N/A N/A mp: Irritant
40.5
181.7
bp:
Pyridine C5H5N 79.1 .982 2 mp: Can cause
-41.6 headaches
, fatigue,
bp: 115 nausea
3,5-dinitrobenzoic C7H4O6N2 212.118 1.7 N/A N/A mp: Irritant
acid 205-
207

bp: 395
Isobutanol C4H10O 74.12 .82 N/A N/A mp: Irritant
(2-methyl-1- -108
propanol)
PRODUCT bp: 108
 Makenna Good
Chemistry 222, Spring 2023
Dr. Easter
02/16/2023

Procedure-
1. Physical Properties
The unknown being tested was Unknown G. It had a clear color and a viscosity slightly thicker
than water. The unknown smelled similar to ethanol, yet sweeter. Unknown G was tested for
boiling point by setting up an apparatus utilizing a hot plate, small reaction tube, and
thermometer. The boiling point was determined to be 90°C, which was corrected to be 89.28°C
(see calculations below).
Barometer reading: 776 mmHg.
Bp Corrected= Bp measured- [Pobs-760 mmHg)(.045 mmHg)]
90-[(776 mmHg-760 mmHg)(.045 mmHg)]
2. Solubility
One drop of the unknown was mixed with 0.5mL of each solvent outlined in Figure 1 to test for
solubility and determine possible functional group presence. Unknown G was soluble in water,
suggesting the presence of a polar functional group. The unknow had a pH of 6 when its solution
water solution was initially tested with pH strips. After adding a few more drops to increase the
concentration of the unknown, the pH remained 6 rather than lowering further, suggesting it was
not a carboxylic acid but likely an alcohol, aldehyde, or ketone.
 Makenna Good
Chemistry 222, Spring 2023
Dr. Easter
02/16/2023

pH>7

pH<7

Figure 1. Solubility flow chart indicating functional groups based on results. The yellow
highlights show the path of Unknown G when tested.

3. Functional Group Classification Tests

a. Ignition Test- A few drops of Unknown G were placed in a porcelain crucible cover and
ignited with a flame starter to test for aliphatic or aromatic functional groups. The
presence of a clear, yellow/orange flame suggested that there was an alkane or substituted
derivative present, but not an aromatic compound.
b. Jones Oxidation Test- One drop of Unknown G was mixed with acetone and Jones
reagent to test for the presence of a primary or secondary alcohol or an aldehyde. The
mixture quickly turned a greenish blue color, which suggested an alcohol due to their
nature of oxidizing rapidly with chromic acid vs. aldehyde groups’ slow oxidation with it.
c. Lucas Test- 0.1 mL of Unknown G was mixed with the Lucas reagent and stirred
vigorously to test for a secondary or a tertiary alcohol. No layers were formed after
several minutes, suggesting the absence of both a tertiary and a secondary alcohol. Paired
with other results in the experiment, this test suggests the presence of a primary alcohol.
d. Dinitrophenylhydrazine Test- 1 drop of Unknown G was mixed with ethanol and 2,4-
dinitrophenylhydrazine reagent. This test is used to test for an aldehyde or ketone
functional group, but it was conducted here to eliminate the possibility of an aldehyde
specifically, which would verify the results of the Jones Oxidation Test. There was no
yellow-red derivative, indicating a negative test result and confirming the absence of an
aldehyde or ketone functional group.
 Makenna Good
Chemistry 222, Spring 2023
Dr. Easter
02/16/2023

4. Spectral Analysis
5. 1H NMR, 13C NMR, Mass Spectrometry, and FTIR were conducted on Unknown G to
further analyze structure. Figures 2-4 show these spectra with annotations to illustrate the
findings. The 1H NMR spectrum shows 4 chemically distinct hydrogen groups with an
integration ratio of 2:1:1:6. This ratio suggests a structure with 10 hydrogens. The
doublet peak further downfield points toward their being two hydrogens that have only
one hydrogen neighbor as a distinct group. The multiplet in the center suggests a
hydrogen with many hydrogen neighbors, and the doublet further upfield suggests six
hydrogens with only one hydrogen neighbor, further from a polarizing group. The 13C
NMR spectrum reveals 3 chemically distinct carbon groups. The spectrum contains a
peak at 20ppm suggesting the presence of methyl groups, a peak at 30ppm suggesting an
R3CH group, and a peak at 70ppm suggesting an RCH2O- group.

Figure 2. 1H NMR and 13C NMR spectra of Unknown G. The red circle indicates the presence of
methyl groups, the blue circle that of an R3CH group, and the green circle that of an RCH2O-
group. Isobutanol, the determined product, is placed for reference with color coded groups. See
Figures 6 and 7 for more information on the isobutanol groups.
 Makenna Good
Chemistry 222, Spring 2023
Dr. Easter
02/16/2023

Figure 3. Mass
spectrometry of
Unknown G and atom
calculation equations.
The molecular ion peak
[M]+ is circled in red, the
base peak is circled in
green, and the [M+1]+ is
highlighted in yellow.
Calculations for the
number of atoms in the
structure are below.

Carbon Calculations:
#C=(0.6/1.1)x(100/13.3)= 4.101 (4)

Mass spectrometry data revealed that there were approximately four carbon atoms in the
structure and that the molecular weight was about 74. The FTIR spectrum of Unknown G shows
a strong, broad curve around 3324.64 cm-1 which represents an O-H bond, confirming the alcohol
identity that was predicted in the initial functional group tests. There were also notable peaks at
2954.64 cm-1 and 2871.66 cm-1, suggesting some sp3 C-H stretch bonds were present.
 Makenna Good
Chemistry 222, Spring 2023
Dr. Easter
02/16/2023

O-H

sp3 C-H stretch

Figure 4. FTIR spectrum of Unknown G.

6. Solid Derivative Synthesis

Based on results from steps 1-3, the appropriate derivative to synthesize was 3,5-dinitrobenzoate.
This derivative was synthesized via a heat and reflux method with a sand bath, ice bath cooling,
and several rounds of vacuum filtration with a Hirsch funnel. Recrystallization was done with
hot ethanol and water, and the precipitate collected to test for melting point with an SRS
DigiMelt Apparatus. Unfortunately, dinitrobenzoyl chloride was not available to use as a reactant
as outlined in the procedure, so 3,5-dinitrobenzoic acid was used in its place. This did not result
in a product that had a viable melting range. The synthesized product before recrystallization was
determined to have a melting point of 165°C, while it was determined after recrystallization to
have a melting point range of 162-167°C. Based on the literature given on unknown and
derivative alcohols, the range for Unknown G’s melting point was predicted to be 50-116°C. It
 Makenna Good
Chemistry 222, Spring 2023
Dr. Easter
02/16/2023
was determined that the synthesized was not the intended derivative and that the melting point
data would not aid in Unknown G’s identification.

Conclusion and Discussion-

Unknown G was identified as 2-methyl-1-propanol, which is also called isobutanol
(C4H10O). According to literature, isobutanol is a clear liquid with a viscosity slightly thicker
than water and a scent that is slightly sweet, yet still reminiscent of ethanol or any alcohol.
Isobutanol has a boiling point of 108⁰C, which is about 20⁰C higher than was initially measured.
This difference can be accounted for by human error and overall variability of the hot plate
boiling point measurement method used. The solubility test pointed to an alcohol group,
aldehyde, or ketone functional group, leading to the need for each of the other functional group
tests to be conducted. A negative for the ignition test indicated no aromatic presence. A quick
positive result for the Jones oxidation test suggested an alcohol functional group being present. A
negative Lucas test indicated the lack of a secondary or tertiary alcohol, and a negative
Dinitrophenylhydrazine test indicated the lack of an aldehyde or ketone functional group. Put
together, the solubility and functional group tests pointed to a primary alcohol, which is what
isobutanol is classified as. This is further verified by the FTIR of Unknown G, which hgihlights
the broad peak of an alcohol functional group. Looking at the unknowns provided in the
literature and matching each up with the spectral analysis results, it became clear that Unknown
G was isobutanol.
Not only does isobutanol possess four chemically distinct hydrogen groups and 3
chemically distinct carbon groups (see Figure 5), but it matches the hydrogen neighboring
projections from the 1H NMR spectrum (see Figure 6). In addition, the 13C NMR spectrum shows
the presence of methyl groups, an R3CH group, and an RCH2O- group. These groups are all
present in isobutanol (see Figure 7). The mass spectrometry data points to four carbons being
present and a molecular weight of about 74. Isobutanol has only four carbons and possesses a
molecular weight of 74.12. Over the course of this experiment, several methods of qualitative
analysis were utilized to examine the physical and chemical properties of Unknown G. Together,
this data matched with unknown and derivative values suggests that Unknown G is isobutanol.

Figure 5. Figure 6. Figure 7.

Isobutanol with hydrogens
drawn. Chemically distinct
hydrogen groups are
highlighted in different
colors. Chemically distinct
carbons are circled in and
labeled in red (1-4).
Isobutanol with hydrogen Isobutanol with circled 13C
neighbor groups highlighted. NMR groups.
These colors can be
referenced in the 1H NMR of
Figure 2.