Professional Documents
Culture Documents
Alcohols and Phenols
Alcohols and Phenols
An important portion of this course is the recognition of organic chemistry functional groups.
These are parts of a molecule, with a specific structure that functions in a certain way. Not only
are you to learn to recognize the functional groups (a listing can be found in your textbook or on
the back cover of this laboratory manual), but you are also to learn the physical and chemical
properties of each of the functional groups studied in the course. This laboratory exercise will
introduce you to two of these functional groups, alcohols and phenols, as well as some of their
physical and chemical properties.
Alcohols
Although you may be familiar with "alcohol as a beverage, the word actually represents an
entire classification of organic molecules and not just one substance. Alcohols contain the
OH (hydroxyl) functional group attached to a saturated carbon. Notice that we did not call this
the hydroxide ion, because this group does not act as an ionic substance.
Alcohols are classified into three categories: primary (1), secondary (2) and tertiary (3). This
classification is based on the number of carbon-containing groups (R for an alkyl or an
aromatic group) attached to the carbon bearing the hydroxyl group. If the carbon bearing the
OH has one R group, the molecule is a primary alcohol. If two R groups are attached, it is a
secondary alcohol. If three R groups are attached, the alcohol is tertiary.
CH3
CH3
CH3
CH3
CH2
OH
CH3
CH
OH
OH
CH3
ethanol
(primary)
2-propanol
(secondary)
2-methyl-2-propanol
(tertiary)
O
H
. Hydrogen bonding
.
.
O
H
H
Procedure:
1. Place 10 drops of each alcohol (ethanol, 1-butanol, 2-butanol, 2-methyl-2-propanol
and 1-octanol) into its own test tube. Add 1-2 ml of water to each tube. Record your
observations on the data sheet.
2. Place another 10 drops of each of the above alcohols into its own test tube. Add 1-2
ml of dichloromethane. Record your observations on the data sheet.
!!CAUTION!!
HCl
ZnCl2
R-Cl + H2O
(insoluble)
Procedure:
3. Place 2 mL of the Lucas reagent in a test tube. Add 4 drops of ethanol. Shake the tube
to mix the materials and note the time required for the mixture to become cloudy or to
separate into two layers. Record your observations. Repeat this procedure for 1butanol, 2-butanol, and 2-methyl-2-propanol.
!!CAUTION!!
CH2
OH +
(primary)
C
OH + Cr2(SO4)3 +
H2CrO4 R
(red-orange)
(carboxylic acid)
(blue-green)
OH
R
CH
H2O
O
R
(secondary)
H2CrO4
(red-orange)
(ketone)
Cr2(SO4)3 +
(blue-green)
H2O
OH
R
H2CrO4
No Reaction
(tertiary)
Procedure:
4. Place 10 drops of acetone in a test tube. Add 5 drops of ethanol and 2 drops of
chromic acid to the tube. Note and record the color of the solution on the data sheet.
Repeat this procedure for 1-butanol, 2-butanol, and 2-methyl-2-propanol.
!!CAUTION!!
Phenols
Phenols are closely related to alcohols because of the presence of the hydroxyl (OH) group. In
phenols, however, the hydroxyl group is directly bonded to an aromatic group, such as benzene.
Phenol compounds often have curious but useful properties. Some are found in preservatives or
medications. The chemistry of phenols is different than that of alcohols. Concentrated solutions
of the compound phenol are quite toxic and can cause severe burns. In this experiment, we are
using an aqueous solution of phenol.
!!CAUTION!!
Phenol is toxic and will cause burns to skin. Even though we are using
an aqueous solution of phenol, any contact should be thoroughly washed
with large quantities of water. Wear safety glasses at all times in the
laboratory. Report all accidents to the instructor.
Note:
In the interest of time, this phenol experiment can be carried out at the same
time as the alcohol experiments. Consult instructor if there is a problem.
!!CAUTION!!
DATA SHEET I
Date
Alcohols & Phenols
Name
Partners
Solubility:
ethanol
Experiment
Solubility in
H2O
Solubility in
CH2Cl2
Comp
letely
Soluble
Partia
lly Soluble
Insolu
ble
Comp
letely
Soluble
Partia
lly Soluble
Insolu
ble
1-butanol
Comp
letely
Soluble
Partia
lly Soluble
Insolu
ble
Comp
letely
Soluble
Partia
lly Soluble
Insolu
ble
2-butanol
Comp
letely
Soluble
Partia
lly Soluble
Insolu
ble
Comp
letely
Soluble
Partia
lly Soluble
Insolu
ble
2-methyl-2propanol
Comp
letely
Soluble
Partia
lly Soluble
Insolu
ble
Comp
letely
Soluble
Partia
lly Soluble
Insolu
ble
1-octanol
phenol
Comp
letely
Soluble
Partia
lly Soluble
Insolu
ble
Comp
Comp
letely
letely
Soluble
Soluble
Partia
Partia
lly Soluble
lly Soluble
Insolu
Insolu
ble
ble
Chemical Properties:
Experiment
Lucas
Test
Chromic Acid
Test
Ferric
Chloride Test
ethanol
1-butanol
2-butanol
2-methyl2-propanol
phenol
DATA SHEET II
Date__________________
Alcohols & Phenols
UNKNOWN # __________
1.
Name_________________________
Partner________________________
A. Hypothesis:
B. Planned Investigation:
C. Observations (data):
D. Conclusion:
2.
A. Hypothesis:
B. Planned Investigation:
C. Observations (data):
D. Conclusion:
3.
A. Hypothesis:
B. Planned Investigation:
C. Observations (data):
D. Conclusion:
4.
A. Hypothesis:
B. Planned Investigation:
C. Observations (data):
D. Conclusion:
REPORT SHEET
Date__________________
Alcohols & Phenols
Name_________________________
Partner________________________
2-BUTANOL
2-METHYL-2-PROPANOL
PHENOL
2. Salicylic acid, shown below, could be (but, it wasnt) used as an unknown. Describe what
you would see/learn as you analyzed this substance if it were your unknown in the
following:
OH
Solubility in water:
O
C
FeCl3 Test:
OH
salicylic acid
3. What results would you expect from the reaction of 1-propanol with each of the following?
Lucas reagent:
Chromic acid reagent:
4. Alcohols are more soluble in water than hydrocarbons are in water. Why?
5. Why does the rule for solubility for alcohols depend upon their molecular size?
6. Most people find, in this experiment, that the result for the solubility of phenol in
dichloromethane is that it is insoluble. This does not seem to make sense to us, as both are
organic and it should be soluble. (Review your results for alcohols in dichloromethane.)
Explain why it appears to be insoluble.