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 unknownTest
T-butanol
2-butanol
2demethyl-
propanol
Phenol
‘Unknown
‘Lucas Test
Oxidation with
Acidified
Dichromate
Ferrie Chloride
Test
Acidity Test
Bromination
Esterification