Identification of the Unknown

Compound
Kristina Somerville
Pejman Golshan
212720983
July 22 & 24, 2014
Submission Date:
July 31, 2014

Introduction
There many discrete compounds present in chemical reactions. There are
similarities among these compounds; however, these can be readily
identified by undergoing certain chemical reactions with specific reagents.
Likewise, by knowing the physical and chemical property of compounds, they
will be placed in different categories such alcohols (primary, secondary,
tertiary), aldehydes, ketones, amines, amides, etc. For instance, in order to
distinguish ketones and aldehydes from the other compounds DNPH test is
exploited, because in DNPH test the carbonyl groups associated with
aldehydes and ketones will be identified (Workman, 1996). Furthermore, to
differentiate aldehydes and ketones from each other, Jones Reagent (CrO3)
can be used. This reagent oxidizes the aldehyde to carboxylic acid. Also, to
indicate the consistency of the results the compound can be identified
Bisulfate addition test (this proves, the unknown is definitely an aldehyde).
Although, these reactions are still practical, they are replaced with more
accurate and modern methods to obtain precise results. For example,
infrared spectroscopy will tell exactly what bonds exist in the structure of the
molecule or H-NMR gives the information about the types of Hydrogen atoms
present in the molecule. These data pave the way to understand the
compounds and render a solid assortment of materials. As an authentic
example, in infrared spectroscopy all compounds with carbonyl groups will
1
have stretches between 1700 and 1800 cm . Moreover, there are other

meticulous methods such as Mass spectrometry and C-NMR which also bring
forward consistent results. Certainly, the best way that leads us to valid
outcome is to implement both old-school and modern methods to see
whether the results are favourable or not.

Results
The unknown underwent Bradys test (2, 4-DNPH Test) and it indicated
positive

result.

In

addition,

affirmative

outcome

is

acquired

from

Semicarbazone test. The melting point of precipitate yield from Bradys test
was within the range of 116 to 121 C. Further, the precipitate yield from
Semicarbazone test was within the range of 89 to 93 C. Moreover, in the
oxidation test after the addition of CrO3, the formation of light green
precipitate was observed. In continuation of previous reactions, the white
crystals were formed by adding NaHSO3 to the unknown solution. Also, the
reaction of the unknown with sodium did not produce any hydrogen gas (no
bubbling observed).

Discussion
The positive results of Bradys and Semicarbazone test confirm that the
unknown is either a ketone or an aldehyde. Moreover, by measuring the
melting point of the precipitates from the tests and comparing it with the
tables of derivative Melting Point, it is inferred that the unknown is butanal
(2,4-DNPH : 123 C, Semicarbazone : 96 C).

In the following reactions,

reagents are exploited to identify the unknown whether its an aldehyde or

not. If the prior results are consistent therefore, the unknown must give
positive result to the oxidation test and produce a carboxylic acid (Pavia,
2007). On the other hand, ketones are not able to undergo the reaction with
CrO3 (only certain ketone without bulky alkyl groups bonded to carbonyl
group). As its expected the light green precipitate formed which indicates
that the unknown is an aldehyde. Furthermore, the addition of sodium
hydrogensulphite certainly proved that the unknown is an aldehyde. The final
step that provides the solid outcome is the sodium test (no bubbling
observed); thus, there is no hydroxyl group in the compound which agrees

with the identity of an aldehyde. However, with these chemical reactions, it

will be cleared that the unknown belongs to which category. Hence, it does
not lead ones to fully identification of the unknown. Consequently, use of
technology such as H-NMR or Infrared spectroscopy becomes enormously

handy. For instance, in the IR spectrum, the peak at 1723

cm

illustrates

the existence of a carbon double bonded to oxygen which confirms the

presence of the carbonyl group in the aldehyde. Furthermore, the stretch

between 2881 and 2966

cm1

states the presence of carbon hydrogen

bonds. In addition, more informative data is given by inquiring the H-NMR

spectrum which exactly tells us how many types of hydrogen atoms are
present in the structure of the compound. For instance, in this unknown
there are 4 types of hydrogen atoms. By adding up the peaks the number of
total hydrogen will be obtained. In this case, there are 8 hydrogen atoms
present in structure which 5 of them belong to alkyl groups, 2 are hydrogen atoms and the last one is bonded directly to carbonyl group. The
proposed structure of the unknown is shown below:
O

H
H3C

The main reason that the H-NMR spectrum prevails over IR spectrum is that, it gives
us the number of hydrogen atoms, more importantly; it differentiates the aldehyde

from ketones. The peak shown on the spectrum (around 9.7 ppm) explicitly
demonstrates that the unknown is an aldehyde.

Conclusion
To sum up, by taking all the data to account, we come to conclusion that the
given unknown is butanal. As its mentioned, it is proven that the unknown is
an aldehyde from the chemical reactions taken place in the laboratory.
Moreover, it highly agrees with IR and H-NMR spectrum. Finally, the numbers
of hydrogen atoms are predicted from H-NMR spectrum and an empirical
model is proposed, which confirms the acquired readings.

References
D. Curtin, J. Gourse, W. Richardson, K. Rinehart, J. Org. Chem, 1959, 24(1),
pp 93-97
G. Karabatsos, B. Shapiro, F. Vane, J. Fleming, J. Ratka, J. Am. Chem. Soc.,
1963, 85 (18), pp 27842788
D. Pavia, Introduction to organic laboratory techniques, 2007, 1, 4th ed, pp
136-137
T. Smith, R. Bonner, Ind. Eng. Chem., 1951, 43 (5), pp 11691173
G. Workman, National Exposure Research, 1996, 1, pp 83-84