EXPERIMENT 2

ALCOHOLS AND PHENOLS

Abarro, Justine Marie E., Andrade, Ehmmarie L., Apego, Jan-Michael V.,
Dimaano, Joshua Gil, Sta. Isabel, Jamie Anne O.
A

INTRODUCTION
Functional groups are certain

a smaller hydrocarbon chain are

groupds of atom within molecules

very much soluble. The length of

that are responsible for the unique

the hydrocarbon chain is inversely

characteristic of a compound when

proportional to the solubility in

it undergoes chemical reactions.

water. With four carbon in the

These specific groups are attached

hydrocarbon chain and higher, the

to the carbon backbone of organic

decrease

molecules. These are far less stable

visible because the mixture can be

than the carbon backbone (Chang

seen separated into two immiscible

et.

are

layers of liquid. The reason why the

expected to contribute in chemical

solubility decreases as the length

reactions. One familiar functional

of hydrocarbon chain increases is

group is the hydroxyl group (OH).

because there is a requirement of

al,

2011).

So,

these

The Hydroxyl group is bound to a

carbon

atom

of

an

organic

compound called alcohols.

more

in

energy

hydrogen

solubility

to

becomes

overcome

the

between

the

bonds

alcohol molecules as the molecules

Alcohols are soluble in water

are more tightly packed together

by nature. The reason for this is

as the size and mass increases

due to the hydroxyl group in the

(Chang et. al, 2011).

alcohol

which

hydrogen

is

bonds,

able
a

to

form
strong

On

the

other

hand,

benzene ring with a hydroxyl group

intermolecular force of attraction,

is

called

with water molecules. Alcohols with

Phenols are

phenol.
also

known as carbolic acid. These

the

organic

compounds

experiments, when phenol is dissolved

compound

in water solvent, two layers of liquid

molecular formula

are formed. The top layer is a solution

are aromatic organic

having

of C6H5OH. The structure of phenol

tells that there is an interaction
between the delocalized electrons in
the benzene ring and one of the lone
pairs on the oxygen atom. This has an
important

effect

on

both

the

properties of the ring and of the

hydroxyl functional group. One of the

lone pairs on the oxygen overlaps

various

conducted

laboratory

of phenol in water, and the bottom

one a solution of water in phenol. The
solubility behavior of phenol and water
is complicated. The objective of the
experiment is to differentiate tertiary
and secondary alcohols from primary
alcohols using the Lucas reagent and
relate nucleophilic substitution ideas
to the use of the Lucas Test. It also
aims to put in practice using acid

with the delocalized ring electron

chlorides to indicate the presence of

system. The donation of the oxygen's

active

lone

system

phenols and comprehend how phenols

increases the electron density around

produce colored ferric complexes. In

the

ring

the experiment, there are 4 different

becomes much more reactive than it is

test to verify the identity of the

in benzene itself. It also helps to

sample. The 4 tests are the Lucas test,

make

the

pair
ring.

into

the

Due

the

to

ring

that,

hydroxyl

the

group's

hydrogen

Acetyl

in

Chloride

alcohols

Test,

and

Ferric

hydrogen a lot more acidic than it

Chloride Test and Bromine in water

is in alcohols (Davis et. al, 2007).

test. The Lucas reagent is an aqueous

The physical properties

phenols

are

of

white

crystalline solid that is volatile in

nature.

Phenol

is

moderately

solution of strong acid (HCl) and zinc

chloride. Based on the component of
the reagent, the expected reaction
that occurs in the Lucas test is an SN1
nucleophilic substitution. Only alcohols

soluble in water. Based on its

that can generate stable carbocation

chemical

intermediates

structure,

phenol

is

will

undergo

the

somewhat soluble in water because of

reaction (Davis et. al, 2007). Acetyl

its ability to form hydrogen bonds with

Chloride test, on the other hand,

the water. However, with regards to

identifies whether the compound is a

phenol

or

alcohol.

Some

cases

intensely colored solution, which is the

resulted to a white solid (Davis et. al,

basis for the test (Davis et. al, 2007).

2007). However, if this happens, as

Finally, the bromine test is a test for

solid could be a derivative for the

the

unknown and water is present in it,

of unsaturation and phenols (Davis et.

the test will probably give a false

al, 2007). The formation of a white

positive test as acetyl chloride reacts

precipitate, which is a brominated

vigorously

phenol, is the basis that could lead

with

water.

The ferric

chloride test is a test to determine the

presence or absence of phenols in a
given sample. Phenols form a violet
complex

IV.

with

Fe3+,

turning

to

presence

to a conclusion that the unknown

was a phenol.

an

References

Chang, Raymond, and Ken A. Goldsby. Chemistry. 11th ed. 1221 Avenue of
the Americas, New

York, NY: McGraw-Hill Companies, 2010.

Davis, Raymond E., M. Larry Peck, and George G. Stanley. Chemistry. By

Kenneth W. Whitten. Eighth ed.
Belmont, California: David Harris, 2007
.