Organic Chemistry Honors Project - Determination of Unknowns

Josh Bietenholz and Terry Clarke

 

(Terry, Josh, & Dr. Gurst)

Our project was for Organic Chemistry. Dr. Breivogel gave each of us an unknown organic substance. Our job was to identify the organic substance. To do so, we had to conduct several tests using a process of elimination. We were only able to perform three of the tests in the chemistry lab here at Chipola. For the rest of these tests, we had to travel to Pensacola to the University of West Florida to use their lab. There, Dr. Jerry Gurst and his assistants helped us to determine the identity of our unknown organic substances.

The three tests we performed at Chipola were: the boiling point test, the 2,4-DNP test, and the flame test. First, we did the boiling point test. This simple test was used to determine the approximate boiling point of our unknown organic substances. Next, we performed the 2,4-Dinitrophenylhydrazine test. In this test, 2,4-DNP was added to the organic unknown. If a reaction takes place, an orange precipitate is formed. This precipitate indicates the presence of an aldehyde or ketone. Then, we performed the flame test. This test is often used to indicate the presence of an aromatic compound. This was all we could accomplish in the lab here at Chipola.

We then traveled to the University of West Florida to use the their lab equipment. With the help of Dr. Jerry Gurst and his assistants, we were able to perform more extensive tests. The first of these tests was done with an infrared spectrophotometer. This test passes infrared radiation through the substance. This infrared radiation is absorbed by the molecules and it excites the vibrational states of the bonds. This absorption is then graphed and used to determine the different types of functional groups present in the molecules. Next, we performed a test using a mass spectrometer. By accelerating ions past a magnetic field, this instrument can determine the molecular weight of the molecule. Lastly, we performed Nuclear Magnetic Resonance spectroscopy. By subjecting our samples to a magnetic field and radio waves, we were able to determine the frequency at which the nucleus of the protons changed from a parallel state to an anti-parallel state. Through this test, we were able to determine the number of different types of protons in each molecule and the number of the neighboring protons. With all of this information, we were able to identify both unknown organic compounds.

Test results are as follows:

 

Terry- Compound A

Josh- Compound B

Boiling point

179 degrees C

132.1-132.8 degrees C

2,4-DNP

Positive

negative

Flame test

positive for aromatic compound

negative for aromatic compound

IR spectroscopy

presence of C=O

presence of OH group

Mass spectrometer

molecular weight- 106

Molecular weight- 86

Proton NMR

two signals

five signals

Compound

Benzaldehyde

isopentyl alcohol

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