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Reference: Laboratory Manual "Chemistry For The Allied Health Sciences," P. 115, Baur, R.D., Campbell, J.A., Loeschen, R.L., and Wolf JL p 1980, Prentice Hall, N. J. IDENTIFICATION OF ORGANIC COMPOUNDS - ALCOHOLS AND PHENOLS INTRODUCTION 41 this experiment, you are going to investigate the reactions of some representative alcohols and phenols. Based upon data that you collect, you wall report the functional group in your unknown as H HHH H CH, H OH “con ote cee i Honk oun primary secondary tertiary phenol alcohoi alcohol aleohol ‘The tests to be performed are, 1) The Lucas Test for primary, secondary and tertiary alcohols: Upon the addition of Lucas Reagent (zine chloride in concentrated hydrochloric acid), a tertiary alcohol gives a white layer within zero to five minutes, a secondary alcohol gives a white layer within five to fifteen minutes; and, a primary alcohol takes several hours. 2) Oxidation with acidified dichromate solution: Primary alcohols are oxidized to aldehydes; secondary alcohols are oxidized to ketones, and tertiary alcohols are not oxidized by acidified potassium dichromate solution. Aldehydes-and ketones have characteristic odors. During an oxidation, the color of the acidified potassium dichromate solution changes to a blue to blue-green, Phenals are oxidized to colored solutions of indeterminate composition or to black or brown tarry masses. 3) The ferric chloride test: Upon the addition of aqueous ferrie chloride, phenols give a colored solution usually green to purple in color. 4) Acidity test - Aqueous solutions of phenols are weakly acidic white aqeous solutions of alcohols are not acidic. The acidity of a solution can be determined by adding Bogan's Universal Indicator to a sotution and noting its color. 5) Bromination Test - Phenols react vigorously with bromine water to form bromination products while alcohols do not. Phenols undergo substitution of ring hydrogens by bromine to form products that are often precipitates, 4) Esterification: Alcohols react with carboxylic acids in the presence of a trace amount of sulfuric acid to form esters, Most esters have a pleasant odor. EXPERIMENTAL A. You are to test I-butanol, 2-butanol, 2-methy!-2-propanol, pheno! (the knowns), and your unknown concurrently, Obtain your unknown before you begin the tests. B. Test each sample as follows: 1, Lucas test: Place 4 drops of the samples and your unknown in separate small test tubes. Add 20 drops of Lucas reagent to each and vortex mix well. Observe carefully during the first five minutes, then every fifteen minutes. Write your observations in the data sheet. 2. Oxidation with acidified dichromate solution. Put 4 drops of your samples and your unknown in separate small test tubes,and add 20 drops of acidified potassium dichromate solution to each. Determine the odor and note the color of each solution, Write your observations in the data sheet, 3. The ferric chloride test: Put one ml (20 drops) of your sample and your unknown in separate test tubes and add 2 drops of ferric chloride solution to each, Note any color changes in each solution, Write your observations in the data sheet. 4, Acidity test: In separate test tubes add 10 drops of the sample and your unknown, Then add 2 drops of Bogan's Universal Indicator to each tube and mix, Compare each tube to the color chart to determine the pH of the substance, Write in the data table both the color observed and the pH. 5. Bromination test Take10 drops of each of the samples and the unknown in separate tubes, Dilute each with 50 drops of distilled water. To each solution add 10 drops of bromine water and mix, Note the results. 6. Esterification: tn separate large Pyrex test tubes, put 60 drops of each sample and of your unknown, Add 60 drops of glacial acetic acid to each and mix well. Then, add about 15 drops of concentrated sulfuric acid to each and mix. Place the test tubes in a warm water bath for five to ten minutes. Determine the odor of each and describe it in the data sheet 7. Based on the data that you collect, write in the data sheet the functional ‘group present in your unknown Test T-butanol 2-butanol 2demethyl- propanol Phenol ‘Unknown ‘Lucas Test Oxidation with Acidified Dichromate Ferrie Chloride Test Acidity Test Bromination Esterification

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