Experiment 7: Qualitative Analysis

Jayden Emberton-Gaines

SCH 213 02

4/26/2018
I. Title: Qualitative Analysis

II. Introduction:

Qualitative Analysis is a process within organic chemistry when an unknown

compound is identified via different constituents and chemicals within. This

experiment is used simply to identify a single unknown chemical, or multiple

chemicals within an unknown compound. Qualitative analysis has no set procedure;

however, many tests are used during a qualitative analysis to be able to determine the

unknown structure. There are however a few steps that need to be completed prior to

determining the structure. Those steps include finding the amount of chemicals

present and discovering the type of functional groups within the chemical. Some of

the tests used during a qualitative analysis include solubility tests, melting point

ranges, IR, NMR, GC, Jones test, and DNP test. Qualitative analysis is an extremely

important technique within the organic chemistry field because as an organic chemist

one often has to identify unknown compounds. Qualitative analysis is also very

important in real world and everyday life, qualitative analysis is often used by

forensic scientist while analyzing evidence found in crime scenes, as well as to test

for lead in the water we drink daily.

The tests within this experiment are very important for the success of determining

the unknown compound. Two important tests are the Jones test as well as the DNP

test. Both of these tests provide identification of specific functional groups. The

Jones test is the first of the two, this test identifies the specific functional groups

within the molecule. Those functional groups identified by the Jones test are

primary/secondary alcohols and aldehydes. In a positive Jones test a cloudy solution

with a blue-greenish color is provided within the first 5 seconds of adding the reagent.

This positive test implies the presence of a primary/secondary alcohol or an aldehyde

functional group. Within a Jones test, primary/secondary alcohols get oxidized to a

carboxylic acid functional group while aldehydes on the other hand get oxidized to a

ketone. The functional groups ketones and tertiary alcohols do not get reduced by the

Jones reagent (chromium trioxide), with that said the Jones reagent does not yield a

positive test. This test is also helpful in everyday life because it is used by law

enforcement to breathalyze drunk drivers when pulled over.

The next test used is called the DNP test or 2,4-dinitrophenylhydrazine test. This

test is used to determine the presence of specific functional groups such as ketones

and aldehydes. A positive DNP test is notified by the formation of a yellow, orange

or red precipitate within the acetone solution. This positive DNP test implies the

presence of a ketone or an aldehyde functional group within the unknown molecule.

The reaction during the DNP test is known as a condensation reaction, this reaction

happens when two molecules join together with the loss of water. Due to a less

electrophilic carbon the DNP reagent will not react with or show the presence of a

ester, carboxylic acid, or amide. This test is important in the identification of a

ketone or aldehyde in an unknown molecule.

 Figure 1. DNP molecular structure

The objective of this experiment was to identify an unknown organic

compound on the basis of IR, Jones test, DNP test, and NMR spectroscopy.

III. Results and Discussion:

The provided unknown organic compound was identified by doing a few

different chemical tests. The first chemical test ran was the Jones test, in the Jones

test a single drop of the unknown compound was dissolved in 1 mL of acetone,

followed by a drop of the Jones reagent. With the addition of the reagent a reaction

occurred, and in this reaction, a blue-greenish solution was formed and signified a

positive test for a primary/secondary alcohol or an aldehyde. The second

identification test was the DNP test. This test used a single drop of the unknown

compound dissolved within 1 mL of ethanol followed by 1 mL of the DNP reagent.

This reaction yielded an orange liquid solution which signified the DNP test was

negative meaning neither a ketone or an aldehyde is present within the unknown

compound. Both an IR spectrum and a proton NMR spectrum were obtained to also

help determine the structure of the unknown liquid organic compound.

The determination of the functional groups present within the unknown

compound relies heavily on the completion of the DNP and Jones tests. These test
each test for different functional groups which when completed helps determine what

the unknown compound can and cannot be. The DNP reagent tests for the presence

of a ketone or an aldehyde functional group. The primary amine reagent is

nucleophilic and used in the reaction to attack the electrophilic carbon and form a

insoluble imine product which forms an orange precipitate look. When the unknown

compound was tested it formed an orange liquid which signifies a negative DNP test.

With the results from this test being negative it is now known that the unknown

compound cannot have an aldehyde or ketone functional group present. The next test

was the Jones reagent test which tests for the presence of a primary/secondary alcohol

or an aldehyde. However, with the negative DNP it is known that the unknown

compound cannot contain an aldehyde functional group. A positive Jones test results

in the formation of a blue-greenish color solution, indicating the presence of a

primary/secondary alcohol or an aldehyde. The Jones test of the unknown compound

produced a cloudy blue-greenish color solution meaning the test is positive and the

unknown compound is a primary/secondary alcohol.

After the unknown compound failed the DNP test and passed the Jones test it is

known that the compound is a primary/secondary alcohol, but an IR and NMR

spectrum were taken to help determine the structure of the primary/secondary alcohol.

The IR and NMR spectrum taken of the unknown compound can be seen in Figures 2

and 3 respectively.
Figure 2. IR spectrum of unknown compound

The IR spectrum of the unknown compound is shown in Figure 2. The IR spectrum

shows many peaks resulting from the unknown compound. The strongest peak seen in the

spectrum happens to be at 3333.31 cm-1 which indicates the presences of an OH stretch in an

alcohol. This peak is expected in the spectrum and helps support the results of the chemical tests

which proved the unknown compound was a primary/secondary alcohol functional group. The

next peak shown is at 3028.39 cm-1 and indicated a C-H stretch in aromatics. This peak is

helpful in identifying the molecular structure of the primary/secondary alcohol, so it is now

known that the alcohol has an aromatic ring attached. The following peaks prior to the

fingerprint range (1250 cm-1 and below) were seen at 2971.68 and 2926.51 cm-1 both
corresponding to a C-H stretch within an alkene. The final peaks shown within the IR were seen

at 1492.83 and 1449.74 cm-1 which both indicate a C-C stretch in a ring. The IR spectrum

suggested that the unknown organic compound was an aromatic primary/secondary alcohol.

Figure 3. Proton NMR spectrum of unknown compound

An NMR spectrum was also taken to determine the exact structure of the unknown

aromatic primary/secondary alcohol. The NMR can be seen above in Figure 3. The NMR

spectrum showed 5 separate peaks, however, one of the peaks shown was at zero ppm which

marks TMS which is used in an NMR as a reference. The remaining four peaks within the NMR

are significant in determining the structure of the unknown aromatic primary/secondary alcohol.
The peak seen furthest downfield is at 7.322 PPM. This peak has an integral of about 5 and is a

singlet. Due to its chemical shift being between the 6.5 and 8 PPM range as well as the integral

of 5 meaning there is one substituent branching off of the ring, it is determined that this peak

corresponds to the aromatic ring that was also present in the IR spectrum. The next peak was

noticeably smaller, this peak was also split into 4 meaning there are 3 hydrogens on the adjacent

carbon. This peak chemical shift was at 4.8 PPM and it had an integral of about 1. The chemical

shift indicated that this peak most likely corresponds to a CH group because it falls in the 4.5-7.5

PPM range of CH on the chemical shift table. The following peak is a singlet seen at 2.1 PPM,

this peak also has an integral of 1. This peak due to its chemical shift, integral and broadness

most likely corresponds to the OH group of the alcohol. The final peak is a doublet, seen at 1.5

PPM. This peak also had an integral of about 3 meaning there are 3 hydrogens branching from

this one carbon atom. With that and the splitting of the peak meaning there is one hydrogen on

the adjacent carbon atom it is evident that this peak corresponds to a CH3 group.

This unknown organic liquid was put through a series of different tests to help identify

the compound and its molecular structure. The chemical tests (DNP & Jones) were used to

determine the functional group present in the compound. With the compound providing a

negative DNP test and a positive Jones test it was suggested that the functional group present

could only be a primary/secondary alcohol. An IR spectrum was taken of the primary/secondary

alcohol to support the chemical tests in that a primary/secondary alcohol functional group was

present in the compound. What this IR spectrum did was confirm the functional group was a

primary/secondary alcohol, and also exposed the presence of an aromatic ring. A proton NMR

was then taken of the aromatic primary/secondary alcohol. Four peaks were shown in this NMR,

the furthest downfield with no splitting corresponds to an aromatic ring with one substituent
branching off, the next peak split into four and corresponds to the CH group that branches off of

the aromatic ring, the third peak is seen is broad and a singlet that corresponds the OH group of

the primary/secondary alcohol that branches from the CH group, and the final peak of the proton

NMR is a doublet that corresponds to the CH3 which also branches off the CH group indicated

by the second peak. With the information provided and data calculated from the DNP test, Jones

test, IR and NMR spectra the final determined structure for the aromatic primary/secondary

alcohol is 1-phenylethanol (Figure 4).

Figure 4. Structure of Unknown Compound (1-Phenylethanol)

IV. Conclusion

In conclusion, the qualitative analysis of an unknown compound was completed

by using the DNP and Jones test to identify the functional group present in the

compound, as well as using the IR (Figure 2) and NMR (Figure 3) spectra to help

determine the structure. The unknown compound was first put through the Jones and

DNP tests. The compound came back negative in the DNP test and positive in the

Jones test providing enough information to know the functional group present is a

primary/secondary alcohol. The IR spectrum then backed up the two chemical tests

by providing peaks of an alcohol and aromatic ring. The proton NMR was the final

step in identifying the structure of the unknown compound and it provided enough

information to allow the structure to be known as 1-Phenylethanol. Overall, this was

a very successful experiment in that everything went very smooth and the unknown

organic compound was correctly identified. The experiment helped strengthen my

knowledge of how to do and how to read IR and NMR spectra, as well as taught me

about qualitative analysis and the Jones and DNP tests.

 References

“Wired Chemist.” Qualitative Analysis, 2018, www.wiredchemist.com/chemistry/instructional/laboratory-

tutorials/qualitative-analysis.

Zhang, S. “Jones Oxidation.” Organic Chemistry, 2005, www.organic-

chemistry.org/namedreactions/jones-oxidation.shtm.

“2,4-Dinitrophenylhydrazine.” Wikipedia, Wikimedia Foundation, 10 Apr. 2018, en.wikipedia.org/wiki/2,4-

Dinitrophenylhydrazine.