Exp.

12 Qualitative Analysis, Gundrum

Qualitative Organic Analysis

Amanda Gundrum
Objective
Two unknown compounds will be analyzed using a series of qualitative tests to
determine the functional groups present, and then the compound will be identified.
Introduction
Qualitative tests are often used as a quick way to figure out they type of organic
compound you have. They allow for chemists to quickly ascertain if a compound has or
doesnt have a certain functional group. This can lead to more focused tests if needed.
In current practice spectroscopic tests may be used more frequently because these
quantitative tests will allow to determine a compound with more certainty, but the
qualitative tests are a quick and easy alternative.
Results
The first compound tested was unknown #1. It was determined to be 3-methyl-1butanol. This was done majorly by using the Colby.edu database. By using the boiling
point and the IR spectra we could narrow the possible compounds down to three
options and then down to one possibility by knowing the compound was a 1 or 2
Alcohol. As the other two options, 2,3,3-trimethyl-2-butanol and 2,4-dimethyl-2-pentanol
are tertiary alcohols.
The second compound tested was an amine. It was determined to be aniline.
Discussion
There were multiple tests performed on each compound, and the IR spectra was
recorded of each unknown. Before any test was performed Unknown #1 was distilled
since it was a liquid at room temperature. This allowed us to find the boiling point, 128
C. From here we calculated the density of the unknowns. This was done by putting 1
mL of the unknown in a tared vial and the weighing the vial. From here we tested the
unknown with chromic acid. This test will tell us if the compound is a primary or
secondary alcohol or an aldehyde. After this we tested the solution with DNPH. A
precipitate would have indicated an aldehyde or a ketone. Finally we tested with
potassium permanganate. If the solution had turned brown it would indicate an alkene.
The final test was Beilsteins Test. For this test a clean copper loop was covered in the
unknown and then burned in a flame. If the test was positive the flame would burn
green, indicating a halogen in the compound. For the unknown amine the Hinsberg test
is required to determine if it was a primary, secondary, or tertiary amine. The amine in
question will first be reacted with sodium hydroxide and p-toluenesulfonyl chloride. A
primary amine is indicated by this solution being soluble initially, and then precipitating
out when the solution is acidified. A secondary amine is indicated by the first reaction
1

Exp. 12 Qualitative Analysis, Gundrum

forming a solid that is insoluble in the basic solution. A tertiary amine is indicated by no
reaction is the beginning, but it becomes insoluble when the solution is acidified. The
generalized mechanisms for these tests are shown under mechanisms. Using the
results from these tests allowed us to determine the identity of our unknown
compounds.
Mechanisms
Potassium Permanganate:

Chromic Acid:

DNPH:

Exp. 12 Qualitative Analysis, Gundrum

Hinsbergs:

Data
For the First Compound:
Test
Result
Distillation (Boiling Point)
128C
Density
0.673 g/mL
Chromic Acid Test
Solution turned blue/green
Beilsteins
Negative
DNPH
No Precipitate
KMnO4
No change
Solubility in water
Insoluble
Solubility in Acid
Insoluble
Table 1. Results for Unknown #1

Means
N/A
1 or 2 Alcohol
Not halogenated
Not an aldehyde/ketone
Not an alkene

Exp. 12 Qualitative Analysis, Gundrum

Figure 1. Unknown #1 IR Spectra

Figure 2. IR Spectra of 3-methyl-1-butanol

Wavenumber (cm-1)
Functional Group
3337.64
-OH (stretching)
2958.46, 2930.93, 2873.65
C-H (sp3, saturated)
1465.43
-OH (bending)
1057.97
C-O (stretching)
Table 2. IR spectra Characteristic Peaks for 3-methyl-1-butanol
For the Unknown amine:
Test
Result
Litmus Test
Blue
Beilsteins
Negative
DNPH
No Precipitate
Solubility in water
Soluble
Solubility in Acid
Soluble
Table 3. Results for the Unknown Amine

Means
Amine present
Not Halogenated

Exp. 12 Qualitative Analysis, Gundrum

Figure 3. IR Spectra of Unknown Amine

Figure 4. IR Spectra of Aniline2

Wavenumber (cm-1)
Functional Group
3431.52, 3354.82
N-H (Stretching)
3213.61
Aromatic H (stretching)
3071.06, 3036.82, 3010.34
=C-H (stretching)
1620.67, 1601.85
N-H (bending)
1276.77, 1174.99
C-N (stretching)
752.96
N-H (bending, fingerprint region)
Table 4. IR Spectra of Characteristic Peaks for Aniline
References
1. Organic Compounds Database
(http://www.colby.edu/chemistry/cmp/cmp.html)
2. Scifinder, 2015; Chemical Abstracts Service: Columbus, OH, 2015;
RN 58-08-2 (20 April 2016).
3. National Institute of Standards and Technology
(http://webbook.nist.gov/chemistry/)
4. Lehman, J. W. Multiscale Operational Organic Chemistry: a Problem-Solving
Approach to the Laboratory Course; Pearson Prentice Hall: Upper Saddle
River, NJ, 2009.