I

II
III
IV

EXPERIMENT TITTLE
EXPERIMENT DATE
END OF EXPERIMENT
EXPERIMENT PURPOSE

: Alcohol and Phenol

: April, 24th 2015 at 13.00 p.m
: April, 24th 2015 at 16.00 p.m
: Distinguish properties of penol and alcohol
Understanding any reaction and reagent that can
be

used

to

distinguish

phenol

and

alcohol

compound
V

BASIC THEORY
Alcohol
In chemistry, an alcohol is any organic compound in which the hydroxyl
functional group (-O H) is bound to a saturated carbon atom. The term alcohol
originally referred to the primary alcohol ethyl alcohol (ethanol), the predominant
alcohol in alcoholic beverages.
Alcohols, the general formula for which is CnH2n+1OH.

Physical and chemical properties

Alcohols have an odor that is often described as biting and as hanging in
the nasal passages. Ethanol has a slightly sweeter (or more fruit-like) odor than the
other alcohols.
In general, the hydroxyl group makes the alcohol molecule polar. Those
groups can form hydrogen bonds to one another and to other compounds (except in
certain large molecules where the hydroxyl is protected by steric hindrance of
adjacent group). This hydrogen bonding means that alcohols can be used as protic
solvents. Two opposing solubility trends in alcohols are: the tendency of the polar OH
to promote solubility in water, and the tendency of the carbon chain to resist it. Thus,
methanol, ethanol, and propanol are miscible in water because the hydroxyl group
wins out over the short carbon chain. Butanol, with a four-carbon chain, is moderately
soluble because of a balance between the two trends. Alcohols of five or more carbons

such as pentanol and higher are effectively insoluble in water because of the
hydrocarbon chain's dominance. All simple alcohols are miscible in organic solvents.
Alcohols, like water, can show either acidic or basic properties at the -OH
group. With a pKa of around 16-19, they are, in general, slightly weaker acids than
water, but they are still able to react with strong bases such as sodium hydride or
reactive metals such as sodium. The salts that result are called alkoxides, with the
general formula RO M+.
Classification of Alcohols
In a primary (1) alcohol, the carbon atom attached to the OH group is bonded to one
other carbon atom. In a secondary (2) alcohol, it is attached to two carbon atoms and
in a tertiary (3) alcohol to three carbon atoms.

Phenol
"Carbolic acid" redirects here. It is not to be confused with carbonic acid.
Phenol, also known as carbolic acid, is an aromatic organic compound with
the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The
molecule consists of a phenyl group (-C6H5) bonded to a hydroxyl group (-OH). It is
mildly acidic and requires careful handling due to its propensity to cause chemical
burns.
Although similar to alcohols, phenols have unique distinguishing properties.
Unlike in alcohols where the hydroxyl group is bound to a saturated carbon atom, in
phenols the hydroxyl group is attached to an unsaturated aromatic (alternating double
and single bond) hydrocarbon ring such as benzene. Consequently, phenols have
greater acidity than alcohols due to stabilization of the conjugate base through
resonance in the aromatic ring.

Properties
Phenol is appreciably soluble in water, with about 84.2 g dissolving in
1000 mL (0.88 M). Homogeneous mixtures of phenol and water at phenol to water
mass ratios of ~2.6 and higher are also possible. The sodium salt of phenol, sodium
phenoxide, is far more water soluble.
Reactions
Phenol is highly reactive toward electrophilic aromatic substitution as the
oxygen atom's pi electrons donate electron density into the ring. By this general
approach, many groups can be appended to the ring, via halogenation, acylation,
sulfonation, and other processes. However, phenol's ring is so strongly activated
second only to anilinethat bromination or chlorination of phenol leads to
substitution on all carbons ortho and para to the hydroxy group, not only on one
carbon. Phenol reacts with dilute nitric acid at room temperature to give a mixture of
2-nitrophenol and 4-nitrophenol while with concentrated nitric acid, more nitro groups
get substituted on the ring to give 2,4,6-trinitrophenol which is known as picric acid.
Aqueous solution of phenol is weakly acidic and turns blue litmus slightly to
red. Phenol is easily neutralized by sodium hydroxide forming sodium phenate or
phenolate, but it being weaker than carbonic acid cannot be neutralized by sodium
bicarbonate or sodium carbonate to liberate carbon dioxide
C6H5OH + NaOH C6H5ONa + H2O
Chemical Properties
We shall focus on chemical reactions that can help to distinguish alcohols from
phenols and to distinguish among the classes of alcohols.
1. Lucas Test.
This test is used to distinguish among primary, secondary, and tertiary
watersoluble alcohols. Lucas reagent is a mixture of concentrated hydrochloric
acid and zinc chloride. Zinc chloride is a Lewis acid, which when added to
hydrochloric acid makes it even more acidic.

2. Iron(III) Chloride Test.

Addition of iron(III) chloride dissolved in chloroform (trichloromethane) to a
phenol dissolved in chloroform, gives a colored solution upon addition of
pyridine. Depending on the structure of the phenol the color of the product can be
most anything from red to violet. Alcohols do not give this test.

VI

MATERIALS AND EQUIPMENT

A MATERIALS
1
2
3
4
5
6
7
8
9

Ethanol
1-Propanol
2-Propanol
N-Butyl alcohol
Sec-Butyl alcohol
Tert-Butyl alcohol
Siclohexanol
Etilen glicol
Phenol

B EQUIPMENT
1 Test Tube
2 Spatula
3 Drops pippete
C

10
11
12
13
14
15
16
17

Resorsinol
O-Kresol
2-Napthol
NaOH 10% solution
Natrium
PP indicator
Lucas reagent
Brom in water

VII

EXPERIMENT PROCEDURE
D

E Solubility
F
0,5 mL or 0,2-0,5 gram
0,5 mL
of ethanol
or 0,2-0,5 gram of0,5
n-butyl
mL oralcohol
0,2-0,5 gram of tert-butyl alcohol
G

Add 2 mL of water
Add 2 mL of water
Add 2 mL of water
Shake
Shake
Shake
Record the observation Record the observation Record the observation

Solubility

Solubility

Solubility

0,5 mL or 0,2-0,5 gram of

0,5cyclohexanol
mL or 0,2-0,5 gram of etyleglicole
0,5 mL or 0,2-0,5 gram of phenol

Add 2 mL of waterAdd 2 mL of water

Add 2 mL of water
Shake
Shake
Shake
Record the observation
Record the observation Record the observation

H
I

Solubility
J

Solubility

Solubility

K Reaction with Alkali

L
M
0,5 mL or 0,2-0,5 gram n-butyl alcohol

0,5 mL or 0,2-0,5 gram cyclohexanol

Add 5 mL NaOH 10 % solution

Shake
Record the observation

N
O
P

0,5 mL or Solubility
0,2-0,5 gram phenol

0,5 mL or 0,2-0,5 Solubility

gram naphtol

Add 5 mL NaOH 10 % solution

Shake
Record the observation

Solubility

Add 5 mL NaOH 10 % solution

Shake
Record the observation

Add 5 mL NaOH 10 % solution

Shake
Record the observation

Solubility

Q
R
S
T
U
V
W
X
Y
Z
AA
AB

AC Reaction with Sodium

AD
AE
AF

2 mL of ethanol
Add a piece of sodium
Add PP indicator
Result

AG
AH
AI
AJ
AK
AL

Add a piece of sodium

Add PP indicator
Result

2 mL of 2- propanol
Add a piece of sodium
Add PP indicator
AM

2 mL of 1-propanol

Result

2 mL of o-cresole
Add a piece of sodium
Add PP indicator
Result

AN
AO
AP
AR
AS
AT
AU

AQLucas Test
Tube 1
2 mL of Lucas reagent

Tube 2
2 mL of Lucas reagent

Add 5 drops of Alcohol (1-butanol) Add 5 drops of Alcohol (2-butanol)

AV
AW
AX
AY

Result

Tube3

2 mL of Lucas reagent

Result

2 mL of Lucas reagent

Add 5 drops of Cyclohexanol

Result

Tube 4

Add 5 drops of tert-butyl alcohol

Result

AZ
BA
BB
BC
BD

BE Oxidation with Chromic Acid

BF
Reagent Bordwell-Welman
BG
25 gram chromate Anhydride (CrO3)

25 mL sulfuric acid concentrated

Dilute with 75 mL distilled water

Reagent Solution

BH
Tube I
(Test of Butanol)

Tube II
(Test of 2-Butanol)

Tube III
(Test of Tert Butyl)

1 mL acetone

1 mL acetone

1 mL acetone

Put in reaction tube

Put in reaction tube
Put in reaction tube
1 drop of alcohol solution (2-butanol)
Add 1 drop of alcohol solution (tert-butyl)
Add 1 drop of alcohol solutionAdd
(1-butanol)
Shake
it
until
the
solution
become
Shake
clearit until the solution become clear
Shake it until the solution become clear
Add 1 drop reagent solution
Add 1 drop reagent solution Add 1 drop reagent solution
BI

Tube IV
(Test of Tryphenyl Carbinol)

Tube V
(Test of Resolsinol)

Colorless

Colorless
1 mL acetone

Colorless
1 mL acetone

Put in reaction tube

Put in reaction tube
Add 1 drop of alcohol solution (tryfenyl Add
carbinol)
1 drop of alcohol solution (resolsinol)
Shake it until the solution become clear Shake it until the solution become clear
Add 1 drop reagent solution
Add 1 drop reagent solution

Colorless
BJ

Colorless

BK
BL
BM
BN
BO
BP
BQ
BR
BS
BT
BU
BV
BX
BY
BZ
CA
CB
CC
CD
CE
CF
CG

BW

Reaction with Phenol and Bromine Water

0.1 gram phenol
Dissolve in 3 mL of water
Add bromine solution until the yellow color not change
Record the result of observation
Result

CH
CI Reaction with Phenol and Iron(III) Chloride
CJ
CK
Tube III
Tube II
Tube I
CL
CM
1/2 crystal or 1/2 solution 2-propanol
crystal or 1/2 solution of resolsinol
1 or 2 crystalCN
/ 1 or 2 solution of1/2
phenol
CO
CP
Add 5 mL water
Add 5 mL water
Add 5 mLCQ
water
CR
Addchloride
1 or 2 drop solution of iron (III) chloride
or 2 drop solution of iron (III)
Add 1 or 2 drop solution of ironAdd
(III)1chloride
CS
Shake it
Shake it
Shake it
CT
Record the result
Record the result
Record the result
CU
Result

Result

Result

VIII

RESULT OF EXPERIMENT
CV
CW

% rendemen

RESULT OF THE EXPERIMENT

Melting Point (0C)

Dark Purple Crystal

B Treatment

H
B
L

- Ethanol =

M Solubility

C Result
I Afte
r
- Ethanol + water =

colorless
colorless soluble
0,5 mL or 0,2-0,5 N
gram0,5
ofmL
ethanol
or 0,2-0,5 gram of n-butyl alcohol
- N-butyl + water =
solution
O
- N-butyl=
solorless partial
P
colorless
soluble
- Cyclohexanol +
Add 2 mLQof water
Add 2 mL of water
solution
Shake
Shake
water = colorless
Robservation
Record the
Record the observation - Cyclohexana
= colorless

solution
- Phenol =

T
U
Solubility

Solubility

V
W

water = colorless

brown
solution
- Aquadest =

not soluble
- Ethylene glikol +

colorless

0,5 mL or 0,2-0,5
gram
phenol
0,5 mL or 0,2-0,5 gram naftol 0.1
1 mL
gram
acetone
phenol
Tube III
Add
mL
ofofwater
Add 2 mL of water
Dissolve
inor231/2
mLsolution
water
1/2
crystal
Add
5 mL
NaOH
10 % 2-propanol
solution
Add
5
mLcolor
NaOH
% solution
Shake
Shake
Add
bromine
solution
until
the
yellow
not10
change
Add
5 Add
mL NaOH
10water
%
solution
Add
5 mL
10
% solution
Shake
2 mL
of
AddNaOH
2 the
mLobservation
of water
Shake
Record
the
observation
Record
Record
the result of observation
Shake
Shake
Record
the observation
Shake
Record Shake
the observation
RecordRecord
the observation
Record Record
the observation
the observation
the observation

Add 5 mL water
- Add 5 mL water
- Add 5Add
mL1 water
or 2 drop solution of iron (III) chloride
- Add 1 or 2 drop
-Test
Addtube
1Shake
or 2 III
itdrop
solution of iron
1 orsolution
2 crystal
/1
Record
result
of the
iron
Solubility
Solubility
2
mL
of
Lucas
chloride
1/2(III)
crystal
or 1/2
chloride of
or (III)
2 solution
Shake
it
- Shake
it
Solubility
Solubility
Solubility
Solubility
% rendemen
Solubility
Solubility
Result
Result
ResultResult
Record the
Record the result

AV Etha
nol

(aq) + H2O(l)

is
solu
ble

(aq) + H2O(l)

in

ADTest Tube II
AE

wate
r
AW

(aq) + H2O(l)

turbid solution (2
soluble

E Con
clus
ion

AC

soluble
- Phenol + water =

AA

0,5
n-butyl
alcohol
or
0,2-0,5
gramgram
cyclohexanol
0,5mL
mLoror0,2-0,5
0,2-0,5gram
gram0,5
of mL
0,5
etyleglicole
mL
or 0,2-0,5
of phenol

AB Test Tube I

layers) not
Y

0,5 mL or 0,2-0,5 gram of0,5

tert-butyl
mL or 0,2-0,5
alcohol gram of cyclohexanol

D Reaction

(aq) +H2O(l)
AF Test Tube
III

- nButy
l is
solu
ble
in

wate
AG

(a
q) + H2O(l)

r
AXCycl
ohex

(aq
) + H2O(l)
AHTest tube IV

anol
is
not
solu
ble

+ HBr(aq)

in

CY
IX

EXPLANATION
CZ

Experiment 1
DA

The purpose of first experiment is testing the solubility between

alcohol and phenol. First we prepare five test tube. In the first test tube add 0.5 mL
colorless ethanol solution and 2 mL of water. The ethanol solution soluble in water.
The reaction is
(aq) + H2O(l)

DB

(aq) +

H2O(l)

DC

In the second test tube add 0.5 mL colorless n-butyl alcohol solution

and add 2 mL of water. N-butyl alcohol partial soluble in water. The reaction is
(aq) + H2O(l)

DD

(aq) + H2O(l)

DE

In the third test tube add 0.5 mL colorless cyclohexanol solution and

add 2 mL of water. Cyclohexanol not soluble in water. It proving by there is two layer
in the test tube. Upper layer colorless thick solution and bottom layer colorless
solution. The reaction is

DF

DG

(aq) + H2O(l)

(aq) + H2O(l)

In the fourth test tube add 0.5 mL etylenglicol and add 2 mL water.

Etylen glicol soluble in water. The reaction is

DH

DI

(aq) + H2O(l)

(aq)

In the fifth test tube ad 0.5 mL brown phenol solution and add 2 mL

water. Phenol not soluble in water. It proving by there is two layer in the solution.
Upper layer is colorless and bottom layer orange solution.
DJ The presence of an electronegative oxygen atom between a carbon and
hydrogen atom creates a permanent dipole in the alcohol and phenol structure. The
negative inductive effect of the electronegative oxygen creates a partial negative
charge on oxygen and partial positive charges on the carbon atom and hydrogen atom

attached to oxygen. Due to the presence of this dipole, alcohols and phenols are
considered to be relatively polar organic compounds. Because of the presence of a
dipole, alcohols and phenols can participate in intermolecular hydrogen-bonding (Hbonding). Intermolecular H-bonding also is a critical determinant of alcohol and
phenol solubility.

DK
DL

Alcohol more soluble than phenol. The relative solubility of alcohols is

dependent on the size and structure of the hydrocarbon portion of the molecule.
Alcohols of three or fewer carbons are infinitely miscible in water because the energy
associated with the alcohol H-bonding with water (H-bond donation and accepting) is
greater than the total energy of vander Waals interactions between the hydrocarbon
portion of these alcohols. As the alcohol hydrocarbon structure increases, the energy
of vanderWaals interactions between hydrocarbon portions becomes to great to
overcome by the energy gained from H-bonding with water. Alcohols with more than
two OH groups are more water soluble than similar alcohols with only one OH
group.

DM
DN

The short chain alcohols are soluble in water, whereas the longer chain

alcohols are insoluble in water. Small alcohols are water soluble because the hydroxyl
group can hydrogen bond with water molecules. But as the size of the alkyl group
increases the solubility in water decreases. This is the result of the alkyl group
disrupting hydrogen bonding among the water molecules. The situation is similar for
phenols. If nonpolar groups (like alkyl groups) are attached to the aromatic ring the
water solubility of the phenol decreases.

DP

DO
From the explanation above, we can concluded that etylen glicol is

most soluble in water because it is alcohol and have two -OH group. So, it is easily
soluble in water. The arrangement of solubility is etylen glicol, ethanol, n-butanol,
cyclohexanol and phenol. Ethanol, n-butanol and cyclohexanol has more alkyl so it is
less solublen than etylen. Phenol not soluble in water because the oxygen s electrons
in the p orbital delocalise into the ring, this reduces the phenols ability to make
hydrogen bonds, which is what solubility in water is about the oxygen uses lone pairs
to make H bond.
DQ

Experiment 2
DR

The purpose of the second experiment is understanding reaction

between alcohol and phenol with alkaly. First we prepare four test tube. In the first
test tube add 0.5 mL colorless n-butyl alcohol solution and add 5 mL of NaOH 10%
solution. The mixture form two layer solution. Upper layer is purple solution and
bottom solution is colorless solution. n- butanol not react with NaOH

DS

DT

(aq) + NaOH (aq)

In the second test tube add 0.5 mL colorless cyclohexanol solution and

add 5 mL NaOH 10% solution. The mixture form two layer. Upper layer is colorless
solution and bottom layer is colorless. Cyclohexanol not react with NaOH

DU

(aq) + NaOH(aq)

DV

In the third test tube add 0.5 mL brown phenol solution and add 5 mL

of NaOH 10% solution. The solution become clear yellow thick solution. the reaction
is

DW

(aq) + NaOH (aq)

+ H2O

DX

In the fourth tube add 0.5 mL colorless naphtol solution. And add 5 mL

NaOH 10% solution. The mixture become dark brown solution and there is black
sediment. The reaction is

DY

(aq) + NaOH(aq)

(aq)

DZ

The principle of this experiment is solubility of phenol and alcohol in

NaOH solution. One major difference is that phenols are typically about a million
times more acidic than alcohols. Addition of sufficient aqueous sodium hydroxide to a
phenol will cause the -OH group of most of the molecules present to be deprotonated;
this will not happen to an alcohol. Most phenols are weaker acids than carboxylic
acids and stronger acids than alcohols. When phenols react with a base the phenol is
converted into a phenoxide anion (see reactions below). The phenoxide anion is more
soluble in water than the corresponding phenol. Consequently, if a water-insoluble
phenol is treated with an aqueous solution of a base that is strong enough to convert
most of the phenol to the phenoxide anion, that phenol will dissolve in the aqueous
base (as the phenoxide salt).

EA
EB
EC From the explanation above we get the conclusion that phenol and
napthol can react with NaOH solution. Because phenol is weakly acidic. Phenol can
lose a hydrogen ion because the phenoxide ion formed is stabilised to some extent.
The negative charge on the oxygen atom is delocalised around the ring. Alcohol

which is n-butanol and cyclohexanol can no react with NaOH because there are not
acidic and not base solution.
ED

Experiment 3
EE

The purpose of third experiment is understanding reaction between

alcohol and phenol with sodium. We prepare three test tube. In the first test tube add 2
mL ethanol and add a piece of sodium metal. The gas release. Then add pp indicator.
The color of solution change from colorless become purple. The function of adding pp
is to know the color changing when the condition of solution change. It is indicated
that the solution become base after adding sodium. The solution become hot. It
indicated that the reaction occur is exotermic. The reaction is

EF

EG

In the second test tube add 2 mL 1-propanol and a piece of sodium.

(aq) + 2Na(s)

(aq) +

H2(g)

The gas release. Then add pp indicator. The color of solution become purple. It is
indicated that the solution become base after adding sodium. The solution become
hot. It indicated that the reaction occur is exotermic.The reaction is
EH

(aq) + 2Na(s)

(aq)

+ H2(g)

EI

In the third test tube add 2 mL of 2-propanol and a piece of sodium.

The gas release. Then add pp indicator. The color of solution become purple. It is
indicated that the solution become base after adding sodium. The solution become
hot. It indicated that the reaction occur is exotermic.The reaction is

EJ

(aq) + 2Na(s)

(aq) +

H2(g)

EK

If a small piece of sodium is dropped into some ethanol, it reacts

steadily to give off bubbles of hydrogen gas and leaves a colorless solution of sodium
ethoxide. From the experiment we know that the gas that produce by ethanol is most
than the other. We can write the gas release ethanol > 1-propanol > 2-propanol.
Primary alcohol more easily react with sodium than secondary and tertiary. The
arrangement of reactivity is ethanol, 1-propanol, 2-propanol.

EL

Alcohols are only slightly weaker acids than water, with a K a value of

approximately 1 10 16. The reaction of ethanol with sodium metal (a base) produces
sodium ethoxide and hydrogen gas.
EM
EN

This reaction is identical to the reaction of sodium metal with water.

EO

EP

However, the latter reaction occurs faster because of the increased acidity of

water (K

value of 1 10

15

). Likewise, similar reactions occur with potassium

metal.
EQ

The acidity of alcohols decreases while going from primary to secondary to

tertiary. This decrease in acidity is due to two factors: an increase of electron density
on the oxygen atom of the more highlysubstituted alcohol, and steric hindrance
(because of the alkyl groups, which inhibit solvation of the resulting alkoxide ion).
Both of these situations increase the activation energy for proton removal. The
basicity of alkoxide ions increases while going from primary to tertiary. This increase
in basicity occurs because the conjugate base of a weak acid is strong. The weaker the
acid, the stronger the conjugate base. From the explanation above we know that the
arrangement of base is 2-propanol, 1-propanol, ethanol.
ER
ES

Experiment 4
ET

The fourth experiment is to distinguish among primary, secondary, and

tertiary water soluble alcohols with Lucas test. Lucas reagent is a mixture of
concentrated hydrochloric acid and zinc chloride. Zinc chloride is a Lewis acid, which
when added to hydrochloric acid makes it even more acidic. Hence, the time taken for
turbidity to appear is a measure of the reactivity of the class of alcohol, and this time
difference is used to differentiate between the three classes of alcohols: In first tube is
filled with 1 mL Lucas reagent, colorless and added with 5 drops 1-butanol solution,
colorless. There is no reaction that happen
EU

CH3(CH2)3OH + HCl

ZnCl 2

no reaction

EV

And the solution is colorless, means that not react much at all. This indicate

that 1-butanol is a primary alcohol. Because primary alcohols will not react much at
all, since a primary carbocation is so unstable so it will not react with Lucas reagent.
EW In second tube is filled with 1 mL Lucas reagent, colorless and added
with 5 drops 2-butanol solution, colorless. There is reaction that happen, because it
form two layer colorless solution. The reaction is
EX

CH3CH(OH)CH2CH3 + HCl

ZnCl 2

CH3CH(Cl)CH2CH3

+H2O
EY

The solution is has two layers/cloudiness in 1 minute. This indicate that 2-

butanol is a secondary alcohol. Because secondary alcohols will react slowly with
Lucas reagent. Secondary alcohols react a bit slower as their carbocations (2 degree)
are not as stable as tertiary alcohol.
EZ

In third tube is filled with 1 mL Lucas reagent, colorless and added

with 5 drops cyclohexanol solution, colorless. There is reaction that happen, because
2 mL of Lucas reagent
it form two layer colorless solution. The reaction is
Add 5 drops of Cyclohexanol

Cl

OH

ZnCl 2

FA

Result

+ HCl

+ H2O(l)

FB The solution is has two layers/cloudiness in 2 minutes after

2 mL of Lucas reagent
cyclohexanol added. This indicate that cyclohexanol is a secondary alcohol. Because
Add 5 drops
of tert-butyl
alcohol
secondary
alcohols
will react slowly with Lucas reagent. Secondary alcohols react a
bit slower as their carbocations (2 degree) are not as stable as tertiary alcohol. Both
Result secondary alcohol in test tube II and test tube III, In the case of secondary alcohols, it
is often the case that the chlorine is attached to the carbon that held the hydroxyl, but
rearrangements are possible. Also The chlorinated product is usually insoluble in
water(the solvent in this reaction), whereas the initial alcohol is usually soluble in
water because of its OH group. Cloudiness appearing in the reaction mixture is taken
as evidence of a positive reaction.
FC

The tertiary alcohol undergoes the most stable reaction and the primary

alcohol undergoes the least stable reaction. The reaction which normally occurs is a
SN1 nucleophilic substitution which is a two steps reaction. Alcohols which have a

capability to form carbocation intermediates exhibit this reaction. Only Secondary and
Tertiary alcohols exhibit SN1 nucleophilic mechanism.
FD
FE
FF
FG
FH

The two steps which are generally followed in this reaction:

1. In the first step the proton (Zn2+) from ZnCl2 will protonate the OH- group of the
alcohol. Water (H2O) attached to the carbon is a weaker nucleophile than Cl
(Chloride). Thus nucleophile Cl- replaces the H2O group forming a carbocation
as its present in excess.
2. In the second step the Cl- attacks the carbocation and thus forms alkyl chloride.
FI

Here the first step is generally the slowest step and is the rate

determining step. As the tertiary carbocation is much stabilized, they are the ones
which undergo reaction and form a turbid solution. The opposite of it happens in the
case of primary alcohols.
FJ

Experiment 6
FK

The sixth experiment is reaction of phenol and bromine water. This

reaction is to detect the presence of phenolic compounds like phenol and cresol. The
test is by added 10 drops of phenol, brown solution into test tube then added by 3 mL
water and added by bromine water, yellow, until the color not changing. In our
experiment it needs 50 drops of bromine water. The reaction that happened is
OH
Br

OH

FL
FM

+ 3 Br2

Br

Br

(2,4,6-tribromo phenol)

There is two layer formed, upper layer is colorless and bottom layer is

orange brown. If bromine water is added to a solution of phenol in water, the bromine
water is decolourised and precipitate(orange) is formed which smells of antiseptic.
This means there is the presence of phenolic compounds in there. The bromine in
water reagent reacts with sites of unsaturation, even aromatic rings, through a
complex addition reaction. The hydroxyl group of the ring activates the ring toward
reaction with the electrophilic bromine. The advantage to using water as the solvent in

this reaction is that the polarity significantly enhances the stability of the reaction
intermediate and increases the overall rate of the reaction. Additional catalysts are not
necessary. Aromatic compounds without the phenol functional group react with
bromine through this mechanism.
FN
FO
FP
FQ
FR
FS

Experiment 7
FT

The seventh experiment is reaction of phenol and FeCl3. This

experiment is to detect the presence of phenolic compounds(phenol). The first tube is

filled with 2 drops of phenol, brown orange. And added with 5 mL of water. After that
added by ferric chloride 2 drops, yellow solution. There is reaction that happen,
because it changing color purple solution. The reaction is
OH

Cl
O

+ FeCl3

FU
FV

Fe
Cl

The solution changing become color purple solution, this indicate that

there is presence of phenolic compounds in phenol. Phenol is acidic, and can form the
phenoxide ion. This ion can complex with iron(III) and form a coloured substance.
The complex reaction is
FW

6C6H5OH + FeCl3 [Fe(OC6H5)6]3- + 6H+ + 3Cl- or

FX
FY

The second tube is filled with 2 drops of resorcinol, brown. And added

with 5 mL of water. After that added by ferric chloride 2 drops, yellow solution. There
is reaction that happen, because there is changing color from orange solution, after
resorcinol added by water to brown clear solution after added by ferric chloride. The
reaction is
FZ

GA
GB
GC
GD

The changing color of this reaction, indicate that there is presence of

phenolic compounds in resorcinol. Resorcinol can form the phenoxide ion. This ion
can complex with iron(III) and form a colored substance.
GE

The third tube is filled with 2 drops of 2-propanol, colorless. And

added with 5 mL of water. After that added by ferric chloride 2 drops, yellow solution.
There is no reaction that happen, because there is no changing color from colorless
solution, after 2-propanol added by water to colorless solution after added by ferric
chloride.
GF
GG
GH +
FeCl3
GI
GJ

The no changing color of this reaction, indicate that there is no

presence of phenolic compounds in 2-propanol. Because 2-propanol is alcohol

compound, alcohol are much less likely to form ions, meaning alcohols cannot
complex the iron(III) ion and therefore cannot form coloured compounds.
GK

The reason use Ferric Chloride (FeCl3) in the lab to test for the

presence (or in some case absence) of phenols, although some -enols will also yield
positive results. The OH (hydroxy group) which is attached directly to an aromatic
nucleus (Benzene, for example) is detected by the Ferric chloride. It is important to
note that alcohols do not undergo the reaction. Phenols will typically yield dramatic
purple,blue,red or green color as an indication of a positive test. FeCl3 will also
indicate the presence of aliphatic acids (that is, non-aromatic organic acids, such as
Acetic acid) turning the solution a yellow color. Aromatic acids will test as a beige-tan
color. Enols will also show a characteristic yellow color.
X

CONCLUSION
GL Based on the experiment it can conclude:
1 Alcohol and phenol has similar (-OH) group in their chain. But have different
physical and chemical properties. Alcohol more soluble in water than phenol,

but phenol more soluble in strong base like NaOH. Phenol is more acidic
2

than alcohol so it is react with metallic sodium.

To distinguish between alcohol and phenol we can use oxidation reaction
with reagent cromate acid also using lucas test with lucas reagent, bromine
water and FeCl3. Phenol with react with three of reagent but alcohol is not
reacted.

XI

GM
QUESTION AND ANSWER
GNQuestion
1 What conclusions can be drawn regarding alcohol solubility in water, based on
the results of the above experiments? Which of the 1-pentanol and 1-Heptanol
2

are more soluble in water?

Write a balanced equation showing the solubility of phenol in 10% sodium

hydroxide solution!
From the above experimental results, which is more acidic, n-hexanol or

phenol? Explain the reason!

Write the equation for the reaction between ethanol and sodium! Are the

instructions saying the results of this reaction?

Based on the above experimental results, how can distinguish between

cyclohexanol and phenol?

How would the effects of lucas reagent to each of the following compounds: 1-

butanol, cyclohexanol and tert-butyl alcohol?

Among the following compounds: 1-butanol, triphenyl carbinol, resorcinol,

which one does not undergo oxidation in testing Bordwell-Wellman?

Write the equation of the reaction between phenol and bromine water! Name

the type of reaction that occurs!

GO
Answer
1. Shorter the chain C is the more easily soluble in water because the hydroxyl
group can form hydrogen bonds with water molecules.
GP
Which is difficult soluble in water is 1- Heptanol, because 1- Heptanol
C group containing as many as 6 so that the chain is getting long and poorly
insoluble in water. Because more chain can distrupt the hydrogen bond
between alcohol and water
2.
OH GQ

+ NaOH

ONa

+ H2O

GR
3. Phenol is more acidic than n-hexanol, because phenol has a -OH group
attached to the aromatic cyclic chain. So readily reacts with a strong base

NaOH. Cyclic aromatic acid chain more than cyclic chain aliphatic alcohols as

4.

can resonate so it is more stable than aliphatic alcohols.

2C 2 H 5 OH + 2 Na 2 C H 3 CH 2 ONa+ H 2
GS

When drops of PP indicator solution turn pink, there are bubbles in the

tube, and the tube was hot.

5. It can distinguish between Phenol and Alcohol(cyclohexanol) using bromine
water . It always gives precipitate white/yellow/orange with Phenols whereas it
does not form any precipitate with alcohols.
6. Lucas reagent toward 1-butanol, there is no reaction occur, thats mean 1butanol is primary alcohol. Then Lucas reagent toward cyclohexanol, is form
two layer in 5-6 minutes, thats mean cyclohexanol is secondary alcohol. And
Lucas reagent toward ter-butyl , form two layer in less time/faster than
cyclohexanol thats mean ter-butyl is tertiary alcohol.
7. Primary and secondary alcohols can be easily oxidized by chromic acid,
whereas tertiary alcohols are not oxidized. So 1-butanol and resorcinol be
oxidized, whereas triphenyl carbinol not.
OH
Br

Br

OH

Br

8.
GT

+
3HBr(aq)

+ 3 Br2
(2,4,6-tribromo phenol)
The bromine in water reagent reacts with sites of unsaturation, even

aromatic rings, through a complex addition reaction.

GU
9.

GVREFERENCES
GW
GX

Anonim. 2015. alcohols and sodium (online)

http://www.chemguide.co.uk/organicprops/alcohols/sodium.html (accessed

GY

April 25th, at 20.00)

Anonim. 2015. Sodium metal as a reagent in organic chemistry Master
Organic Chemistry (online)
http://www.masterorganicchemistry.com/2011/10/07/reagent-friday-sodium-na/

GZ

(accessed April 25th, at 20.00)

Anonim. 2015. The Reaction Between Alcohols and Sodium Chemwiki
(online)
http://chemwiki.ucdavis.edu/Organic_Chemistry/Alcohols/Reactions_of_Alcoh
ols/The_Reaction_Between_Alcohols_and_Sodium (accessed April 25th, at

HA

20.00)
Anonim. 2015. Reactions of Alcohols (online)
http://www.cliffsnotes.com/sciences/chemistry/organic-chemistry-ii/alcohols-

HB

and-ethers/reactions-of-alcohols (accessed April 25th, at 20.00)

Anonim. 2015. the acidity of phenol (online)
http://www.chemguide.co.uk/organicprops/phenol/acidity.html (accessed April

HC

25th, at 20.00)
Fessenden and Fessenden. 1986. Kimia Organik: Edisi Ketigas. Terjemahan

HD

Aloysius Hadyana Pudjaatmaka Ph. D.. Jakarta: Erlangga

Tim Dosen Kimia Organik. 2015. Penuntun Praktikum Kimia Organik I.
Surabaya:Unipress
HE

HF ATTACHMENT
HG

Solubility

HH
Poured 0.5 mL
ethanol into test tube
I = colourless
solution

HI Tu
HJ
HK

Poured 0.5 mL nbutyl alcohol into

test tube II =
colourless solution

Poured 0.5 mL
cyclohexanol into
test tube III =
colourless solution

HL
Poured 0.5 mL
ethyleneglicol into
test tube IV =
colourless solution

HM
HN
HO

Poured 0.5 mL
phenol into test
tube V = brown
solution

Added 2 mL of
water in each test
tube

HP
Shake each test tube

HQ
HR

Ethanol + water =
colorless solution
(soluble)

n-butyl alcohol +
water = colourless
solution (partial
soluble)

HS
Cyclohexanol +
water = colorless
solution (not soluble,

Ethylene glycol +
water = colorless
solution (soluble)

phenol + water =
turbid solution (not
soluble, two layer)

HT
HU

HW
HX

HV
Prority of solubility of soluble insoble is
ethylene glycol > ethanol > n-butanol >
cyclohexanol > phenol

HY
HZ Reaction with Alkali

IA
Poured 0.5 mL nbutyl alcohol into
test tube I =

IB
IC
ID

Poured 0.5 mL
cyclohexanol into
test tube II =
colourless solution

Poured 0.5 mL
phenol into test
tube III = brown

IE
Put 0.5 mL naphtol
into test tube IV =
back powder

IF
IG

Poured 5 mL NaOH
10% into each test
tube

n-butyl alcohol +
NaOH 10% +
shake = colorless
solution (two

IH
cyclohexanol +
NaOH 10% + shake
= colorless solution
(two layer)

phenol + NaOH
10% + shake =
light yellow thick
solution

naphtol+ NaOH
10% + shake =
brownish solution
and black

II
IJ

IL

IK
n- butyl alcohol and cyclohexanol not react with
NaOH. Phenol and naphtol react with NaOH

IM
IN Reaction with sodium

IO

Poured 2 mL ethanol
into test tube I =
colourless solution

Poured 2 mL 1propanol into test tube

II = colourless

Poured 2 mL 2propanol into test tube

III = colourless

IP
Added a small
metallic Na =
yellowish colorless +
gas

Added
phenolptalein
indicator and shake

Ethanol + metallic
Na + phenolptalein
+ shake = pink
magenta solution

IQ
IR

IS
1-propanol +
metallic Na +
phenolptalein +
shake = pink

IT
IU
IV
IW
IX
IY
IZ
JA
JB
JC Lucas Test

2-propanol +
metallic Na +
phenolptalein +
shake = pink

React arrangement
Ethanol > 1propanol > 2propanol

JD
Poured 1 mL lucas
reagent into each test
tube = colourless
solution

JE
JF
JG

Poured 1 mL lucas
reagent + 1-butanol
into test tube I =
colourless solution

Poured 1 mL lucas
reagent + 2-butanol
into test tube II =
two layers
colourless solution (

JH
Poured 1 mL lucas
reagent +
cyclohexanol into test
tube III = two layer
colourless solution

Cyclohexanol and 2-butanol (secondary

alcohol) can react with Lucas reagent proven by
two layers in solution

JI
JJ
JK
JL
JM
JN
JO
JP Reaction with Phenol with Bromine Water

JQ
Poured 0.5 mL
phenol into test tube
= brown solution

JR
JS
JT

JU
phenolJV
+ 3 mL of
water + bromine
water intoJW
test tube =
upper is colourless,
bottomJX
is orange-

Poured 0.5 mL
phenol + 3 mL of
water into test
tube

Poured 0.5 mL
phenol + 3 mL of
water + bromine
water into test tube
= orange-yellow

JY
JZ
KA
KB
KCReaction with phenol with Iron (III) Chloride

KD
Poured 2 drops of
phenol into test tube
I = brown solution

KE
KF

Poured 2 drops pf
resolsinol into test
tube II = blackish
brown solution

Poured 2 drops of
2-propanol into test
tube III =
colourless solution

KG
Added 5 mL of
water in each test
tube

KH
KI
KJ
KK
KL
KM
KN
KO

Added 2 drops of
FeCl3 in each test
tube

Tube I: 2 drops of
phenol + 5 mL of
water + 2 drops of
FeCl3 = purple
solution

KP
KQ

Tube II: 2 drops of

resorsinol + 5 mL of
water + 2 drops of
FeCl3 = clear brown
solution

Tube I: 2 drops of
2-propanol + 5 mL
of water + 2 drops
of FeCl3 =
colorless solution

Phenol and
resorsinol react
with FeCl3 but 2propanol not react