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Experiment 16

Alcohols and Phenols


Goals:
1. To learn some common properties of alcohols and phenols.
2. To distinguish phenols from the three types of alcohols by chemical tests.
Concepts:
Alcohols are organic compounds containing an -OH functional group bonded
to a carbon atom. There are three classes (types) of alcohols: primary
secondary and tertiary as sho!n belo!.

"rimary alcohol:
#CH
2
-OH
the $#% an al&yl group and the 'OH are attached
to a primary carbon atom a carbon bonded to one other carbon atom
(highlighted).
H
C
OH
R
H
H
C
OH
H
3
C
H
#
primary carbon
(econdary alcohol:
#
2
CH-OH
the 2 $#% al&yl groups and the -OH are
attached to a secondary carbon atom a carbon attached to t!o other carbon
atoms from the 2 $#%()H*-)
H
C
OH
R
R
H
C
OH
H
3
C
H
3
C
#
#
secondary carbon
Tertiary alcohol:
#
*
C-OH
the * $#% al&yl groups and the 'OH are attached to
a tertiary carbon atom (highlighted) a carbon attached to three other carbon
atoms from the * $#% ()H*-)
R
C
OH
R
R
CH
3
C
OH
H
3
C
H
3
C
#
#
tertiary carbon
#
The +nternational ,nion of "ure and Applied )hemistry (+,"A)) method of
nomenclature for alcohols use the ending ol . )hange the $e% ending of an
al&ane to ol (i.e. methane to ol methanol ethane to ol ethanol).
1
Physical Properties of Alcohols:
1. Alcohols are colorless at room temperature.
2. Alcohols form hydrogen bonds !ith !ater.
H
O
H O
H R
*. Alcohols form intermolecular hydrogen bonds (!ith itself).
This causes alcohols to ha-e higher boiling points than
hydrocarbon of similar molecular mass.
R
O
H O
H R
.. Alcohols !ith / or less carbon atoms are soluble in !ater.
Chemical Properties of Alcohols:
1. O0idation of alcohols by strong o0idants such as 12)r2O2 in H2(O. is
possible but differs depending on the degree of alcohol. 30amples a b and c
belo! sho! ho! a primary secondary and tertiary alcohol respecti-ely
respond to treatment of o0idants. +f a reaction has occurred using 12)r2O2 in
H2(O. there is a color change from orange to green.
a)
1
2
Cr
2
O
2
4
45
R
C
H
O
)r
4*
4
#)H
2
OH
primary
alcohol aldehyde
green6blue
orange

R
C
H
O
R
C
OH
O
7urther o0idation of
carbo0ylic acid
)H
*
)H
2
OH 4 )r
45
)r
4*
green6blue orange
4
H
3
C
C
H
O
an aldehyde
further
o0idation
H
3
C
C
OH
O
a carbo0ylic acid
a primary alcohol
2
b)
1
2
Cr
2
O
2
4
45
R
C
R
O
)r
4*
4
#
2
)HOH
secondary
alcohol
&etone
green6blue
orange
4 )r
45
)r
4*
green6blue orange
4
H
3
C
C
CH
3
O
a &etone
8O
further
o0idation
OH
C H
3
C
H
CH
3
a secondary
alcohol
c) Tertiary alcohol: #*)OH 4 12)r2O2 8O O9+:AT+O8

4 )r
45
orange
OH
C H
3
C
CH
3
CH
3
a tertiary
alcohol
8o reaction (still orange)
2. ;ucas Test: This test is for lo! molecular !eight alcohols and it distinguishes
the rates of reaction of alcohols !ith the ;ucas reagent (H)l and <n)l2).
"ositi-e indicator of the reaction is the formation of a !ater insoluble al&yl
chloride as cloudiness or a precipitate. The formation of an al&yl chloride
!ith tertiary alcohol is -ery rapid follo!ed by the secondary alcohol that may
ta&e from / to 2= minutes to form -isible cloudiness. "rimary alcohols do not
react !ith ;ucas reagent or it may sho! -ery little result in a -ery long time.
*
o
alcohol: #*)OH 4 H)l (<n)l2) #*)l (al&yl chloride) 4 H2O >ery 7ast
(insoluble6cloudiness)

4
CH
3
C H
3
C
CH
3
OH
*
o
alcohol
H)l
<n)l
2
CH
3
C H
3
C
CH
3
Cl
4 H
2
O
al&yl chloride
(insoluble-cloudiness)


*
2
o
alcohol: #2)HOH 4 H)l (<n)l2) #2)H)l (al&yl? chloride) 4 H2O (lo!
(insoluble6cloudiness)


4
CH
3
C H
3
C
H
OH
2
o
alcohol
H)l
<n)l
2
CH
3
C H
3
C
H
Cl
4 H
2
O
al&yl chloride
(insoluble-cloudiness)
slo!
1
o
alcohol: #)H2OH 4 H)l (<n)l2) 8o reaction6-ery -ery slo!

4
H
C H
3
C
H
OH
1
o
alcohol
H)l
<n)l
2
no reaction (no cloudiness)
Phenols:
"henolic compounds ha-e a ben@ene ring !ith the 'OH group attached to the
ben@ene ring carbon atom. The simplest compound is phenol ()5H/OH) or
OH
. "henols are considered -ery !ea& acids. They ha-e different
physical and chemical properties from alcohols. They neither undergo o0idation
nor react !ith the ;ucas reagent.
Ho!e-er phenols react !ith 7e)l* to form a para-phenol-7e comple0 (!hich has
a purple color).
4
7e
4*
OH
(orange)
OH
Fe
para phenol comple0
(purple)
Materials:
5 medium si@e test tubes ethanol (ethyl alcohol) 2-propanol (isopropyl alcohol)
tertiary butyl alcohol (2-methyl-2-propanol) phenol cyclohe0anol 2A 12)r2O2
in H2(O. (o0idant) H)l '<n)l2 (;ucas reagent) 2= A phenol 1A 7e)l* pH
paper stirring rod and an un&no!n
Wear safety goggles and dispose of chemicals in proper containers.
Procedures:
.
o all parts of this experiment in the fume hood.
1. (olubility in Bater:
"lace 2= drops of each alcohol phenol and an un&no!n in 5 separate test
tubes in a test tube rac& labeling each test tube. Add 2 m; of distilled !ater
to each test tube. +f the substance is soluble (miscible) in !ater there !ill be
no separate layers. +f it is insoluble (immiscible) a cloudy mi0ture or layers
!ill form. #ecord your obser-ation in the table belo!.
2. Acidity:
To each test tube in step 1 dip a stirring rod and touch it to the pH paper.
)ompare the color of the paper !ith the chart on the container to chec& the pH
of the solution. Bash and dry the stirring rod before dipping it to the ne0t test
tube. #ecord your obser-ations in the table belo!.
*. O0idation of alcohols:
)lean / test tubes !ith soap and !ater and dry the test tube !ith a paper
to!el. ;abel each test tube and place them on a test tube rac&. "lace / drops
of the alcohols phenol and an un&no!n in each test tube. Add * drops of the
o0idant (12)r2O2-H2(O.) to each test tube. Obser-e if there is a change in
color from orange to green6blue for the alcohols. #emember that only the
primary and secondary alcohols undergo o0idation. The positi-e indicator is a
change from orange to green6blue in 1-2 minutes. )olor change to any other
color but green6blue is a negati-e reaction. #ecord your obser-ations.
.. 7erric )hloride Test for "henolic compounds:
)lean / test tubes !ith soap and !ater and dry the test tube !ith a paper
to!el. ;abel each test tube and place them on a test tube rac&. "lace / drops
of the alcohols phenol and an un&no!n in each test tube. Add * drops of 1A
7e)l* to each test tube. The positi-e indicator is the purple color of the
phenol-7e comple0. Any color other than purple is negati-e.
Obser-ation (heet for "rocedures 1-.
8ame of
substance
(olubility
in !ater
Acidity
)olor
change
(orange to
green6blue)
#eaction product
(aldehyde &etone
7e-comple0)
Type
of
alcohol
phenol
n6a
ethanol
2-propanol
cyclohe0anol
t-butyl alcohol
/
Cour un&no!n
/. ;ucas% #eagent Test:
Deasure 2 m; of the ;ucas reagent into fi-e labeled test tubes on a test tube
rac&. Add / drops of each of the follo!ing to each test tube: ethyl alcohol 2-
propanol cyclohe0anol t-butyl alcohol and deioni@ed !ater as a control.
Di0 reagents !ell using a stirring rod. Bash and dry your stirring rod after
each use. Obser-e and record formation of an insoluble product (cloudiness)
the positi-e indicator that a reaction has ta&en place at different times.
Alcohols Type of
alcohols
(1
o
2
o
*
o
)
1
minute
(cloudy)
*
minutes
(cloudy)
/
minutes
(cloudy)
1=
minutes
(cloudy)
1/
minutes
(cloudy)
3thanol
2-propanol
)yclohe0anol
t-butyl alcohol
(2-methyl-2-
propanol)
your un&no!n
!ater
,se the results of the tests for alcohol and phenol to identify your un&no!n. Ei-e
reasons !hy you belie-e your un&no!n is FFFFFFF. Gustify your ans!er.
5
!uestions:
1. (ince all alcohols form hydrogen bond !ith !ater does this mean
all alcohols are soluble (miscible) in !aterH BhyH
2. Brite the structure for each of the follo!ing alcohol identify !hat
type of alcohol (its degree) and !rite the reaction product !ith an
o0idant 12)r2O2-H2(O.. +f no reaction occurs !rite 8#.
2
* a) 2-pentanol
b) 1-methyl-cyclopentanol
c) 1-he0anol
d) 2-methyl-2-butanol
e) methylphenol
*. Brite the structure for each of the follo!ing alcohols identify !hat type
of alcohol (its degree) and !rite the reaction product !ith the ;ucas
reagent. +f no reaction !rite 8#.
.
/ a) 2-pentanol
b) 1-methyl-cyclopentanol
c) 1-he0anol
d) 2-methyl-2-butanol
e) methylphenol
.. +f you add 12)r2O2 in H2(O. to a test tube !ith an un&no!n alcohol in it
and the solution stays orange !hat can you conclude about the alcoholH
2
I