ALCOHOLS AND PHENOLS

Alfafara, N.B.D., Bernal, R.G.T., Fabro, B.T., Rayos, P.R.P. Department of Biology, University of the Philippines Baguio July 30, 2013 ABSTRACT INTRODUCTION RESULTS Table 1. Solubility of different alcohols and phenol in Water

Compound 0.5 ml ethyl alcohol 0.5 ml n-butyl alcohol 0.5 ml sec-butyl alcohol 0.5 ml tert-butyl alcohol 0.5 ml benzyl alcohol 0.5 ml glycerol 0.5 g phenol and n-nitrophenol Table 2. Rate of gas evolution with Na metal Compound 1. N-butyl alcohol 2. Sec-butyl alcohol 3. Tert-butyl alcohol 4. Phenol

Result + 1 ml, insoluble +2 ml, insoluble + 2 ml, slightly soluble + 2 ml, insoluble + 2 ml, insoluble + 2 ml, soluble +2 ml. insoluble

Result (compared with the rest of the compounds) Slow Faster than compounds 1 and 3 Faster than compound 1 only Fastest, with moisture forming around the sides of the test tube

Table 3. Mixture 5 drops of ethanol, 5 drops of glacial CH3COOH, 1 drop H2SO4 5 drops of ethanol, 5 drops of glacial CH3COOH, 1 drop H2SO4, phenol Table 4. Lucas Test Compound n-Butyl Alcohol sec-Butyl Alcohol tert-Butyl Alcohol Odor Plastic balloon-like Paste-like

Results No separation into layers No separation into layers No separation into layers

Table 5. Oxidation of Alcohols Compound n-Butyl Alcohol sec-Butyl Alcohol tert-Butyl Alcohol Table 6. Iodoform test of Ethanol 1 ml H2O, 5 drops ethanol, 5 drops 8 N NaOH, iodine in KI Table 7. Reaction of Phenol Mixture Phenol, 1 ml water, bromine water Ethanol, FeCl3 Phenol, FeCl3 Phenol, KMnO4

Result Dark blue, butter odor Dark blue, acetone Dark blue

Clear solution with yellow precipitate

Result Cloudy upper layer with red ppt. No color change Dark brown/purple Brown precipitate

DISCUSSION A. Solubility in Water Ethanol is soluble in water because there is a hydrogen bond formed between molecules of ethanol and water molecules.1 The hydrocarbon chain in ethanol is also short, making it infinitely soluble in a given quantity of water.2 B. Reaction of the OH group 1) In four separate test tubes with n-butyl alcohol, sec-butyl alcohol, tert-butyl alcohol and phenol, a small piece of Na metal was added to each. As a precautionary measure, the test tubes were cleaned with the reagents to remove water as Na metal is explosive when reacted to it. 2) 3) Lucas Test Lucas reagent is used to classify alcohols as primary, secondary, or tertiary depending on whether the hydroxyl group is attached to a carbon that is bound to one, two or three other carbon atoms with n-butyl alcohol, sec-butyl alcohol and tert-butyl alcohol subjected to classification. N-butyl alcohol did not separate into two layers after ten minutes, showing that primary alcohols are not converted to chloride even for several hours at room temperature. Hypothetically, sec-butyl alcohol should dissolve to give a clear solution then form chlorides within five minutes as being a secondary alcohol and tert-butyl alcohol should react instantly, giving an insoluble alkyl chloride layer as being a tertiary alcohol.3 But contrary, C. Oxidation

The alcohols oxidized were n-butyl alcohol, sec-butyl alcohol and tert-butyl alcohol. The alcohols were added with 10% K2Cr2O7, 10 drops of dilute H2SO4 and warmed in a water bath. N-butyl alcohol turned from blue to dark blue solution with the smell of a rancid butter. During the process, the n-butyl alcohol, as a primary alcohol, is initially oxidized to butyraldehyde; however by heating under reflux the aldehyde is further oxidized to butyric acid, a carboxylic acid.4 Secbutyl alcohol also turned from blue to dark blue solution with an acetone-like odor. The reaction is similar to the one with the primary alcohols, but the placement of the OH group results in the production of 2-butanone, a ketone. There is no oxidation reaction present in tert-butyl alcohol because as a tertiary alcohol, the hydroxyl group bonded to a carbon atom is bonded to three other carbon atoms, making that carbon atom no hydrogen to be removed by the oxidizing agent. D. Iodoform Test The iodoform test is used to identify alcohols that have a methyl group on the alcohol carbon.5 Water is added to ethanol and 5 drops of 8 N NaOH. Iodine in KI was added dropwise and the solution was then heated. The yellow color of the solution became clear and triiodomethane, CHI3, is formed as a yellow precipitate. The formation of the precipitate is an indication of a positive result. Ethanol is the only primary alcohol to give a positive result in this test because of its presence of CH3CHOH group. E. Reaction of Phenol 1) Reaction with Br2. H2O In a test tube with 1 ml water, few drops of phenol was added, heated and then added with bromine water dropwise. A red liquid precipitate was formed, an indication of incomplete reaction because a white precipitate should form as a result of multiple substitution reaction of bromine in the benzene ring. 2) Test for the enol groups in phenol To test the presence of enol group, 10% FeCL3 was added in 2 separate test tubes. In one test tube, 3 drops of ethanol was further added. There is no observable change, retaining its yellow orange color. There is no reaction present because there is no enol group in ethanol. Few drops of phenol were added in another test tube. Color change from yellow orange to dark brown/ purple is evident as result of the formation of iron-phenol complex.6 3) Reaction with aqueous neutral KMnO4

CONCLUSION

LITERATURE CITED 1. Solubility of Alkanes. Retrieved July 28, 2013, from, http://www.oit.edu/libraries/che102/chapter_2_5.pdf 2. Alcohols and Ethers. Retrieved July 28, 2013, from http://chemed.chem.purdue.edu/genchem/topicreview/bp/2organic/alcohols.html 3. Reactions of Hydrocarbons. Retrieved July 28, 2013, from http://www2.ucdsb.on.ca/tiss/stretton/chem2/orglab1.htm 4. Reactions of Alcohol. Retrieved July 28, 2013, from http://www.slideshare.net/ssvyas123/reactions-of-alcohol 5. Alcohols and Phenols. Retrieved July 28, 2013, from http://www.laney.edu/wp/chelifossum/files/2012/01/6-Alcohols-and-Phenols.pdf 6. Alcohols and Phenols. Retrieved July 28, 2013, from http://facstaff.gpc.edu/~msakuta/chem1152L/lab4.pdf 7. http://www.umb.edu.pl/photo/pliki/WF_jednostki/zaklad-chemii-medycznej/lab._5.pdf

APPENDIX ANSWERS TO QUESTIONS