BIOORGANIC CHEMISRTY

BioOrganic Chemistry CH 205 (2013-2014) Experiment 6

Characterization of Oxygen-Bearing Organic Compounds

Danielle Karol H. Reyes, Karlo Jonathan A. Salem*, Ericka L. San Juan, and Maria Daniela P. Santos Department of Sports Science, College of Rehabilitation Sciences, University of Santo Tomas, Espaa Street, Manila 1008
Date Submitted: August 7, 2013 _____________________________________________________________________________________________ Abstract: The following experiment was conducted to: identify th different structural features of oxygen-bearing compounds, characterize oxygen-bearing organic compounds based on their chemical reactions, deduce the structural feature of an unknown compound through parallel tests with known standards and lastly, to derive the chemical equations involved in each test. This experiment was conducted following several specific tests for oxygen-bearing organic compounds namely: the Dichromate Test, DNPH Test, Iodoform Test, Lucas Test and Tollens Test. It was through the use of different reagents and techniques that the characteristics of each standard compounds were observed and distinguished. After the reactions have been noted, it was compared to the reactions with that of the unknown and of the other compounds. During the experiment, test tubes and droppers are primary materials used, as well as the specific reagents to be used in each particular test. _____________________________________________________________________________________________

1. Introduction Oxygen-bearing organic compounds could have diferent structural features. These structural features could either be alcohol (ROH), ether (ROR), aldehyde (RCHO), ketone (RCOR), ester (RCOOR), etc. No specific chemical test can differentiate one from the other. A combination of several chemical tests could reveal a particular functionality. The objectives of

this experiment are the following: to identify tge different structural features of oxygen-bearing compounds, to characterize oxygen-bearing organic compounds based on their chemical reactions, to deduce the structural feature of an unknown compound through parallel tests with known standards, and to derive the chemical equations involved in each test. 2. Methodology There are several tests that were conducted for this experiment. For the Dichromate Test, 5 drops of test compounds are placed in separate test tubes. 5 drops of 10% K2Cr2O7 and 5 drops 6M H2SO4 were added. Color changes were observed and compared to the reagent. For the DNPH Test, 5 drops of test compounds were placed in separate test tubes. 10 drops of DNPH reagent were added. The formation of precipitate was observed. For the Iodoform Test, 5 drops of test compounds were placed in separate test tubes. 10 drops of 10% KI solution were added. It was added slowly while shaking 10 drops 5% NaClO solution. It was then heated in boiling water. The color and appearance of precipitate was noted down. For the Lucas Test, 5 drops of test compounds was placed in separate test tubes. 10 drops of concentrated HCl and a microspatulaful of dry ZnCl2 was added. The mixture was then shook and the time of appearance of cloudiness or insoluble layer was noted down. For the Tollenss Test, 20 drops of freshly prepared Tollens reagent was placed in separate test tubes. 5 drops of test compounds was added to each test tube. It was then mixed well and warmed in a warm bath. Any change seen was noted down. 3. Results and Discussion

Table 1: Data of Results of the Different Tests Standards Dichromate Test 1 ROH 1-Propanol Blue-Green Solution (+) DNPH Test Yellow orange no precipitate (-) 2 ROH 2-Propanol Blue-Green Yellow Iodoform Test Colorless liquid no precipitate (-) Colorless Colorless Copper Lucas Test Colorless liquid (-) Tollens Test Gray liquid black precipitaite

Solution (+)

orange no precipitate (-)

liquid yellow green solid (-)

liquid (-)

liquid no precipitate

3 ROH

Tert-Butanol

Orange Solution (-)

Yellow orange no precipitate (-)

Colorless liquid no precipitate (-)

Colorless liquid Turbid Solution (+)

Copper liquid

Aldehyde

Formaldehyde

Blue-Green Solution (+)

Yellow precipitate (+)

Orange liquid no precipitate (-)

Colorless liquid no precipitate (-)

Colorless liquid silvermirror precipitate (+)

Ketone

Acetone

Orange Solution (-)

Yellow precipitate (+)

Orange liquid yellow precipitate (+)

Colorless liquid white precipitate

Colorless liquid no precipitate

Unknown

Orange Solution

Yellow orange no precipitate

Orange liquid yellow precipitate

Colorless liquid with white precipitate

Colorless liquid no precipitate

Based on the results shown in the table, it is clear that different tests yields different results because of the different reagents used in each test. Nevertheless, it is clear to which test compound will yield positively (+) and which will yield negatively (-).

4. Conclusion Since oxygen-bearing organic compounds have different structural features, they also yielded different results as compared to other oxygen-bearing organic compounds. After the experiment, one can identify and characterize the oxygen-bearing organic compounds based on their chemical reactions with the different tests done. 5. References Moore, J.W., Stanitski, C.L. & Jurs, P.C. (2010) Principles of Chemistry:The molecular science. Belmont, California: Brooks-Cole Pavia, D.L., Kriz, G.S, Lampman, G.M., & Engel, R.G. (1999). Introduction to organic laboratory techniques: A microscale approach. (Third Ed.). Pacific Grove, California: Brooks-Cole.

________________________ *Karlo Jonathan A. Salem