A.

EXPERIMENT TITLE : Alcohol, Phenol, and Carboxylic

Acid.
B. EXPERIMENT STARTED DATE : Wednesday, February 26th, 2020 at
07.00 am.
C. EXPERIMENT FINISHED DATE : Wednesday, February 26th, 2020 at
12.00 pm.
D. PURPOSE OF EXPERIMENT :
1. To distinguish the properties between alcohol and phenol.
2. To know the types of reactions and reagents that can be used to
distinguish between alcohol and phenol compounds.
3. To identify organic compounds that contain functional groups of
carboxylic.
E. BASIC THEORY
1. Alcohol
a. Definition
Alcohol is a compound such as water whose hydrogen is replaced
by a hydrocarbon chain or ring. Physical properties of alcohol, alcohol
has a high boiling point compared to alkanes with the same number of C
atoms. This is because the alcohol molecules form hydrogen bonds. The
general formula of R-OH alcohol, with R is an alkyl both aliphatic and
cyclic. In alcohol, the more branches the lower the boiling point.
Whereas in water, methanol, ethanol, propanolol is soluble and only
butanol is slightly soluble. Alcohol can be a runny liquid and easily mix
with water in all its comparisons (Brady, 1999).
Alcohol is also an alkane hydrocarbon derivative, where the
hydrogen atom in an alkane is replaced with the -OH group to form an R-
OH molecule formula where R is an alkyl group with CnH2n+1 or CnH2n+1-
OH. The name IUPAC alcohol is taken from the name of the parent
alkane, but with the suffix "ol". If more than one hydroxyl group is used,
di, tri, tetra are used, just before the -ol suffix (Fessenden and Fessenden,
1986).
 The part that a role in an alcohol is the hydroxyl group coupled to
the alkyl group. Alcohol can be thought of as a derivative of water, with
one hydrogen atom replaced by a carbon atom from an organic molecule.
Many properties of low molecular weight alcohol are similar to the
nature of water. (Hart, et al. 2003)

H—O—H
(water) (an alcohol)

b. Alcohol Classification
Alcohols are classified as primary (1o), secondary (2o) or tertiary
(3o). Alcohols are differentiated based upon the presence of hydroxyl
group attached. If one carbon atom is bound to a carbon atom that has an
OH group, then the alcohol is the primary alcohol. If two carbons which
are bound to carbon atoms are clustered OH then they are said to be
secondary alcohols. And if it is bound to three carbon atoms it is referred
to as tertiary alcohol.
Another feature of alcohol is its reaction with acids to produce
esters and dehydration to produce alkenes or ethers. Alcohol which has
two groups -OH in the molecule is called dial (dihydric alcohol) and for
alcohol which has three groups -OH is called thiol (Daintith, 1990).
 Primary alcohol
Primary alcohols (1o) are those alcohols where the carbon
atom of the hydroxyl group (OH) is attached to only one single
alkyl group.

 Secondary alcohol
 In a secondary (2o) alcohol, the carbon atom with the -OH
group attached is joined directly to two alkyl groups, which may
be the same or different.

 Tertiary alcohol
In a tertiary (3o) alcohol, the carbon atom holding the -OH
group is attached directly to three alkyl groups, which may be any
combination of the same or different groups.

c. Nomenclature
As with other types of organic compounds, alcohols are named by
both formal and common systems. The most generally applicable system
is that adopted at a meeting of the International Union of Pure and
Applied Chemistry (IUPAC) in Paris in 1957.
The name IUPAC alcohol is taken from the name of the parent
alkane, but with the -ol suffix. A prefix number that is selected as low as
possible, is used if needed. It can be more than one hdroxyl group, used
di, tri, and so on, just before the -ol suffix. Note the ending a in the name
of the parent alkane is fixed, then just given a "d" consonant from the
diol suffix (Fessenden and Fessenden, 1986).
The common name of an alcohol combines the name of the alkyl
group with the word "alcohol", e.g., methyl alcohol, ethyl alcohol. Propyl
alcohol may be n-propyl alcohol or isopropyl alcohol, depending on
whether the hydroxyl group is bonded to the end or middle carbon on the
straight propane chain. As described under systematic naming, if another
group on the molecule takes priority, the alcohol moiety is often
indicated using the "hydroxy-" prefix.
d. Physical Properties
 Boiling Point
The boiling points of alcohols are much higher than those
of alkanes with similar molecular weights. For example, ethanol,
with a molecular weight (MW) of 46, has a boiling point of 78 oC
(173 oF), whereas propane (MW 44) has a boiling point of −42 oC
(−44 oF). Such a large difference in boiling points indicates that
molecules of ethanol are attracted to one another much more
strongly than are propane molecules. Most of this difference
results from the ability of ethanol and other alcohols to form
intermolecular hydrogen bonds.
 Solubility of Alcohol
The solubility of alcohol in water decreases when the
molecular weight of alcohol increases. Hydrogen bonds between
alcohol molecules and water explain the solubility of the first 5
alcohols in water. The longer the hydrocarbon part, the lower the
solubility of alcohol in water. This is because the increase in van
der waals forces between parts of hydrocarbons from alcohol
becomes more effective in attracting alcohol molecules to each
other. thus defeating the effects of hydrogen bond formation.
Therefore, methanol dissolves in water in all comparisons while
dexol is insoluble. Conversely, if the more -OH groups, alcohol
molecules will dissolve easily in water.
The solubility level of ethylene glycol is greater than
ethanol because the hydrocarbon chain in ethylene glycol consists
of only 2 C atoms while the hydroxyl group possessed by
ethylene glycol is 2. The solubility rate of ethanol is greater than
tert-butyl alcohol because the hydrocarbon chain in ethanol only
consists of 2 atoms C. Where, the hydrophilic nature (like water)
of the hydroxyl group defeats the hydrophobic nature of the
alcohol. So that it causes ethanol to mix with water. The solubility
level of tert-butyl alcohol is greater than that of n-butyl alcohol
 because it consists of 4 C atoms and the hydrophilic nature (like
water) of the hydroxyl group of tert-butyl alcohol defeats the
hydrophobic nature of the alcohol.
 Viscosity
The viscosity of alcohols increase as the size of the
molecules increases. This is because the strength of the
intermolecular forces increases, holding the molecules more
firmly in place.
 Polarity
Alcohol is ranked third in terms of polarity due to its
hydrogen bonding capabilities and presence of one oxygen atom
in an alcohol molecule. Carboxylic acids are more polar than
alcohols because there are two oxygen atoms present in a
carboxylic acid molecule.
 Flammability
The flammability of alcohols decrease as the size and mass
of the molecules increases. Combustion breaks the covalent bonds
of the molecules, so as the size and mass of the molecules
increases, there are more covalent bonds to break in order to burn
that alcohol. Hence, more energy is required to break the bonds,
therefore the flammability of alcohols decrease as size and mass
of molecules increases.
e. Chemical Properties
 Combution
Alcohol burns in oxygen to produce carbon dioxide and water.
Alcohol burn cleanly and easily, and does not produce soot. It
becomes increasingly more difficult to burn alcohols as the
molecules get bigger. The general molecular equation for the
reaction is:
CnH2n+1OH + (1.5n)O2 → (n+1)H2O + nCO2
 Oxidation of Alcohol
 Alcohols can be oxidized into carboxylic acids. E.g. oxidation of
ethanol:
C2H5OH + [O]  CH3COOH + H2O
Oxidation can be done by using oxidising agents such as acidified
potassium dichromate (VI), acidified potassium manganate (VII).
 Dehydration of Alcohol
Dehydration of alcohols is done by heating with
concentrated sulfuric acid, which acts as the dehydrating agent, at
180°C. This reaction uses alcohols to produce corresponding
alkenes and water as byproduct.
f. The Preparation of Alcohol
 Reduction of Aldehydes and Ketones
The most obvious way to reduce an aldehyde or a ketone to
an alcohol is by hydrogenation of the carbon–oxygen double
bond. Like the hydrogenation of alkenes, the reaction is
exothermic but exceedingly slow in the absence of a catalyst.
Finely divided metals such as platinum, palladium, nickel, and
ruthenium are effective catalysts for the hydrogenation of
aldehydes and ketones (Carey, 2000).
Aldehydes yield primary alcohols:

Pt, Pd, Ni, or Ru

+ H2 RCH2OH
(aldehyde) (hydrogen) (primary alcohol)
Ketones yields secondary alcohols:

Pt, Pd, Ni, or Ru

C + H2 RCH(OH)R'
(ketones) (hydrogen) (secondary alcohols)
 Reduction of Carboxylic Acids and Esters
Carboxylic acids are exceedingly difficult to reduce. Acetic
acid, for example, is often used as a solvent in catalytic
hydrogenations because it is inert under the reaction conditions. A
 very powerful reducing agent is required to convert a carboxylic
acid to a primary alcohol. Lithium aluminum hydride is that
reducing agent (Carey, 2000).
1. LiAlH4, diethyl ether
RCOOH RCH2OH
2. H2O

(carboxylic acid) (primary alcohol)

Sodium borohydride is not nearly as potent a hydride donor
as lithium aluminum hydride and does not reduce carboxylic
acids. Esters are more easily reduced than carboxylic acids. Two
alcohols are formed from each ester molecule. The acyl group of
the ester is cleaved, giving a primary alcohol (Carey, 2000).
RCOOR'  RCH2OH + R'OH
(ester) (primary alcohol) (alcohol)
 Hydrolysis of Haloalkanes
Haloalkanes can be converted to corresponding alcohols
using aqueous sodium/potassium hydroxide or water as
nucleophiles.
CH3CH2Cl + NaOH  CH3CH2OH + NaCl
g. The Uses of Alcohol
In laboratories and industry, alcohol is used as a solvent and
sorensia. Alcohol derivatives are mainly used for:
1) Antiseptics in surgery and on the skin, for example ethanol and
isopropylalkohol.
2) Preservatives, for example benzyl alcohol, phenityl alcohol and
chlorobutano.
3) Sterilize air in the form of aerosols, for example ethylene glycol,
propylenglycol and trimethylene glycol.
2. Phenol
a. Definition
Compounds that have a hydroxyl group directly attached to a benzene
ring are called phenols. Thus, phenol is the specific name for
hydroxybenzene, and it is the general name for the family of compounds
derived from hydroxybenzene (Solomon and Fryhle, 2011).
 (phenol) (4-methylphenol)
Phenol has an alcohol-like group but its functional group attaches
directly to the aromatic ring. The name is usually used by a name that is
common with the suffix –ol. General formula of Phenol: C6H5OH.
Phenol is an acid that is stronger than alcohol or water. Fenold with pKa
= 10 with acid strength approximately in the middle between ethanol and
acetic acid. Fenoxide ion is a weaker base than OH, because of that,
phenoxide can be treated with a phenol and NaOH in water. This activity
is very different from alcohol reactivity. Phenol is more acidic than
alcohol because anions are produced by resonance, with negative
contents spread (delocalized) by aromatic rings (Fessenden and
Fessenden, 1986).
Phenol is a acid that is stronger than alcohol especially because the
phenoxide ion is stabilized by resonance. The negative charge on the
alkoxide ion is concentrated in the oxygen atom, but the negative charge
on the phenoxide ion can be delocalized to the position of the ortho and
para rings through resonance (Hart et al., 2003).
Phenols are similar to alcohols but form stronger hydrogen bonds.
Thus, they are more soluble in water than are alcohols and have higher
boiling points. Phenols occur either as colourless liquids or white solids
at room temperature and may be highly toxic and caustic.
In industry, phenol is used as a starting material to make plastics,
explosives such as picric acid, and drugs such as aspirin. The common
phenol hydroquinone is the component of photographic developer that
reduces exposed silver bromide crystals to black metallic silver. Other
substituted phenols are used in the dye industry to make intensely
 coloured azo dyes. Mixtures of phenols (especially the cresols) are used
as components in wood preservatives such as creosote.
b. Nomenclature
An old name for benzene was phene, and its hydroxyl derivative
came to be called phenol. This, like many other entrenched common
names, is an acceptable IUPAC name. Likewise, o-, m-, and p-cresol are
acceptable names for the various ring-substituted hydroxyl derivatives of
toluene. More highly substituted compounds are named as derivatives of
phenol. Numbering of the ring begins at the hydroxyl-substituted carbon
and proceeds in the direction that gives the lower number to the next
substituted carbon. Substituents are cited in alphabetical order (Carey,
2000).

(phenol) (m-cresol) (5-chloro-2-methylphenol)

The three dihydroxy derivatives of benzene may be named as 1,2-,
1,3-, and 1,4benzenediol, respectively, but each is more familiarly known
by the common name indicated in parentheses below the structures
shown here. These common names are permissible IUPAC names
(Carey, 2000).

(1,2-benzenediol) (1,3-benzenediol) (1,4-benzenediol)

c. Physical Properties
 The physical properties of phenols are strongly influenced by the
hydroxyl group, which permits phenols to form hydrogen bonds with
other phenol molecules and with water. Thus, phenols have higher
melting points and boiling points and are more soluble in water than
arenes and aryl halides of comparable molecular weight. Some ortho-
substituted phenols, such as o-nitrophenol, have significantly lower
boiling points than those of the meta and para isomers. This is because
the intramolecular hydrogen bond that forms between the hydroxyl group
and the substituent partially compensates for the energy required to go
from the liquid state to the vapor (Carey, 2000).
The presence of hydroxyl groups in phenols means that phenols are
like alcohols in some respects. For example, they are able to form strong
intermolecular hydrogen bonds, and therefore have higher boiling points
than hydrocarbons of the same molecular weight. Phenol (bp 182oC) has
a boiling point more than 70°C higher than toluene (bp 110.6oC), even
though the two compounds have almost the same molecular weight.
Phenols are also modestly soluble in water because of their ability to
form strong hydrogen bonds with water molecules (Solomons and
Fryhle, 2011).
 Pure phenol is a white crystalline solid, smelling of disinfectant.
It has to be handled with great care because it causes immediate
white blistering to the skin. The crystals are often rather wet and
discoloured.
 Melting and boiling points: It is useful to compare phenol's
melting and boiling points with those of methylbenzene (toluene).
Both molecules contain the same number of electrons and are a
very similar shape. That means that the intermolecular attractions
due to Van der Waals dispersion forces are going to be very
similar. The reason for the higher values for phenol is in part due
to permanent dipole-dipole attractions due to the electronegativity
of the oxygen - but is mainly due to hydrogen bonding. Hydrogen
bonds can form between a lone pair on an oxygen on one
 molecule and the hydrogen on the -OH group of one of its
neighbours.
 Phenol is moderately soluble in water - about 8 g of phenol will
dissolve in 100 g of water. If you try to dissolve more than this,
you get two layers of liquid. The top layer is a solution of phenol
in water, and the bottom one a solution of water in phenol. The
solubility behaviour of phenol and water is complicated. Phenol is
somewhat soluble in water because of its ability to form hydrogen
bonds with the water.
d. Chemical Properties
One important characteristic of the phenol group that distinguishes
it from the alcohol group is its acidity, in the sense that phenol is more
acidic than alcohol, due to the presence of resonant stabilization in
phenoxide ions. In ethoxide ions, the negative charge is localized to the
oxygen atom. In the phenoxide ion the negative charge is delocalized in
the ortho position and the in the benzene ring. This type of charge results
in greater stability of the phenoxide ion than the ethoxy ion. When in
phenols there are halogen subtituents or nitro groups, it is evident that the
presence of these substituents affects the acidity of phenols.
e. The Preparation of Phenol
 Reaction of benzenesulfonic acid with sodium hydroxide
This is the oldest method for the preparation of phenol.
Benzene is sulfonated and the benzenesulfonic acid heated with
molten sodium hydroxide. Acidification of the reaction mixture
gives phenol (Carey, 2000).

1. NaOH 300–350oC

2. H+

 Hydrolysis of chlorobenzene
 Heating chlorobenzene with aqueous sodium hydroxide at
high pressure gives phenol after acidification (Carey, 2000).

1. NaOH, H2O 370oC

2. H+

f. The Uses of Phenol

 Approximately two-thirds of the total phenol produced worldwide
is used to prepare reagents used in plastic manufacturing
industries. We cannot imagine our lives without plastic. Most of
the things around us are either made from plastics or have plastic
components in them. The condensation reaction of phenol with
acetone produces bisphenol A which is extensively used in
polymer industries to synthesis various epoxide resins and
polycarbonates.
 The polymerization reaction of phenol with formaldehyde is used
to commercially prepare phenolic resins. The resulting resin is
known as phenol-formaldehyde resin, commercially it is
marketed by the name of bakelite. Bakelite is extensively used in
electrical switches and automobiles due to its property of
withstanding extreme conditions of heat and resistance to
electricity and other chemicals. The intermediate produced during
the polymerization reaction is called novolac, this is a resin and is
used as a binding agent or adhesive in many industries. Novolac
is also used for protective coating purposes.
 Phenol is also used in the study and extraction of bio-molecules.
Molecular biology finds the application of phenol in the
extraction of nucleic acids from tissue samples for further
investigations.
 Phenol is also used in the cosmetic industry in the manufacturing
of sunscreens, skin lightening creams and hair colouring
solutions.
3. Carboxylic Acid
a. Definition
Any of a class of organic compounds in which a carbon (C) atom is
bonded to an oxygen (O) atom by a double bond and to a hydroxyl group
(―OH) by a single bond. A fourth bond links the carbon atom to a
hydrogen (H) atom or to some other univalent combining group. The
carboxyl (COOH) group is so-named because of the carbonyl group
(C=O) and hydroxyl group.
Carboxylic acids are similar in some respect to both ketones and
alcohols. Carboxylic acids (RCO2H). Simple derived from open-chain
alkanes are systematically named by replacing the terminal –e of the
corresponding alkane name with –oic acid.

Carboxylic acids are polar substances. Their molecules can form

strong hydrogen bonds with each other and with water. As a result,
carboxylic acids generally have high boiling points, and low-molecular-
weight carboxylic acids show appreciable solubility in water. As the
length of the carbon chain increases, water solubility declines (Solomons
and Fryhle, 2011).
The chief chemical characteristic of the carboxylic acids is their
acidity. They are generally more acidic than other organic compounds
containing hydroxyl groups but are generally weaker than the familiar
mineral acids (e.g., hydrochloric acid, HCl, sulfuric acid, H2SO4, etc.).
b. Nomenclature
Systematic or substitutive names for carboxylic acids are obtained
by dropping the final -e of the name of the alkane corresponding to the
longest chain in the acid and by adding -oic acid. The carboxyl carbon
atom is assigned number 1 (Solomons and Fryhle, 2011).
The following examples show how this is done:

(butanoic acid)
 Many carboxylic acids have common names that are derived from
Latin or Greek words that indicate one of their natural sources.
Methanoic acid is called formic acid (formica, Latin: ant). Ethanoic acid
is called acetic acid (acetum, Latin: vinegar). Butanoic acid is one
compound responsible for the odor of rancid butter, so its common name
is butyric acid (butyrum, Latin: butter). Pentanoic acid, as a result of its
occurrence in valerian, a perennial herb, is named valeric acid. Hexanoic
acid is one compound associated with the odor of goats, hence its
common name, caproic acid (caper, Latin: goat). Octadecanoic acid takes
its common name, stearic acid, from the Greek word stear, for tallow
(Solomons and Fryhle, 2011).
c. Physical Properties
Carboxylic acids are polar substances. Their molecules can form
strong hydrogen bonds with each other and with water. As a result,
carboxylic acids generally have high boiling points, and low-molecular-
weight carboxylic acids show appreciable solubility in water. As the
length of the carbon chain increases, water solubility declines (Solomons
and Fryhle, 2011).
The solubility of carboxylic acids in water is similar to that of
alcohols, aldehydes, and ketones. Acids with fewer than about five
carbons dissolve in water; those with a higher molecular weight are
insoluble owing to the larger hydrocarbon portion, which is hydrophobic.
The sodium, ammonium, and potassium salts of carboxylic acids,
however, are generally quite soluble in water. Thus, almost any
carboxylic acid can be made to dissolve in water by converting it to such
a salt, which is easily done by adding a strong base—most commonly
sodium hydroxide (NaOH) or potassium hydroxide, (KOH). The calcium
and sodium salts of propanoic (propionic) acid are used as preservatives,
chiefly in cheese, bread, and other baked goods.
The melting points and boiling points of carboxylic acids are
higher than those of hydrocarbons and oxygen-containing organic
 compounds of comparable size and shape and indicate strong
intermolecular attractive forces (Carey, 2000).
Carboxylic acids have much higher boiling points than
hydrocarbons, alcohols, ethers, aldehydes, or ketones of similar
molecular weight. Even the simplest carboxylic acid, formic acid, boils at
101oC (214oF), which is considerably higher than the boiling point of
ethanol (ethyl alcohol), C2H5OH, which boils at 78.5oC (173oF), although
the two have nearly identical molecular weights. The difference is that
two molecules of a carboxylic acid form two hydrogen bonds with each
other (two alcohol molecules can only form one). Thus, carboxylic acids
exist as dimers (pairs of molecules), not only in the liquid state but even
to some extent in the gaseous state.
Therefore, boiling a carboxylic acid requires the addition of more
heat than boiling the corresponding alcohol, because (1) if the dimer
persists in the gaseous state, the molecular weight is in effect doubled;
and, (2) if the dimer is broken upon boiling, extra energy is required to
break the two hydrogen bonds. Carboxylic acids with higher molecular
weights are solids at room temperature (e.g., benzoic and palmitic acids).
Virtually all salts of carboxylic acids are solids at room temperature, as
can be expected for ionic compounds.
In aqueous solution intermolecular association between carboxylic
acid molecules is replaced by hydrogen bonding to water. The solubility
properties of carboxylic acids are similar to those of alcohols. Carboxylic
acids of four carbon atoms or fewer are miscible with water in all
proportions (Carey, 2000).
Unbranched-chain carboxylic acids (fatty acids) that are liquids at
room temperature, especially those from propanoic (C3) to decanoic (C10)
acid, have very foul, disagreeable odours. An example is butanoic
(butyric) acid (C4), which is the main ingredient in stale perspiration and
thus the chief cause of ―locker-room‖ odour.
d. Chemical Properties
  Carboxylic acids are weak acids and their carboxylic anions are
strong conjugate bases are slightly alkaline due to the hydrolysis
of carboxylate anion compared to other species, the order of
acidity and basicity or corresponding conjugate bases are as
follows:
Acidity RCOOH > HOH > ROH > HC CH > NH3 > RH
Basicity RCOO– < HO– < RO– < HCC– < NH2- < R–
 The carboxylic acids react with metals to liberate hydrogen and
are soluble in both NaOH and NaHCO3 solutions. For example,
2CH3COOH + 2Na → 2CH3COO– Na+ + H2
CH3COOH + NaOH → CH3COO– Na+ + H2O
CH3COOH + NaHCO3 → CH3COO– Na+ + H2O + CO2
The carboxylic acids react with metals to liberate hydrogen and
are soluble in both NaOH and NaHCO3 solutions. For Example
Carboxylic acids dissociate in water to give resonance stabilised
carboxylate anions and hydronium ion.
 Lithium aluminium hydride can reduce an acid to an alcohol; the
initial product is an alkoxide from which the alcohol is liberated
by hydrolysis.
4 R–COOH + 3LiAlH4 → 4H2 + 2LiAlO2 + (RCH2O)4 AlLi + H2
Hydrolysis of (RCH2O)4 → alcohols
e. The Preparation of Carboxylic Acid
 Side-chain oxidation of alkylbenzenes
A primary or secondary alkyl side chain on an aromatic ring is
converted to a carboxyl group by reaction with a strong oxidizing
agent such as potassium permanganate or chromic acid (Carey,
2000).
KMnO4 or
ArCHR2 K2Cr2O7, H2SO4
ArCO2H
 Oxidation of primary alcohols
Potassium permanganate and chromic acid convert primary
alcohols to carboxylic acids by way of the corresponding
aldehyde (Carey, 2000).
 KMnO4 or K2Cr2O7,
RCH2OH H2SO4
RCO2H
 Oxidation of aldehydes
Aldehydes are particularly sensitive to oxidation and are
converted to carboxylic acids by a number of oxidizing agents,
including potassium permanganate and chromic acid (Carey,
2000).
Oxidizing agent
RCOH RCOOH
f. The Uses of Carboxylic Acid
Carboxylic acid make up a series of fatty acids which are
extremely good for human health. The omega-6 and omega-3 are
essential fatty acids which are not produced by the body. They help in
maintaining the cell membrane and control nutrient use along with
metabolism. If we consume a meal with unsaturated fat, the glucose and
other nutrients will directly rush into the bloodstream without being
absorbed. Whereas if there is an intake of saturated fat, digestion will
slow down and body will get more time to absorb the energy and
nutrients from the meal.
The following points will state other significant uses of carboxylic acids:
 Manufacturing of soaps need higher fatty acids. Soaps are
generally sodium or potassium salts of higher fatty acids such as
stearic acid.
 Food industry uses many organic acids for the production of soft
drinks, food products etc. For example, acetic acid is used in
making vinegar. Sodium salts of organic acids find application in
preservatives.
 In pharmaceutical industry organic acids are used in many drugs
such as aspirin, phenacetin etc.
 Acetic acids are often used as a coagulant in the manufacturing of
rubber.
 Organic acids find huge application in making dye stuff,
perfumes and rayon.
F. EQUIPMENTS AND MATERIALS
Equipments
 Test tube 10 pieces
 Spatula 1 piece
 Spirtus burner 1 piece
 Pipette 20 pieces
 Graduated cylinder 10 mL 2 pieces
 Beaker glass 100 mL 2 pieces
 Clasp 1 piece
 Test tube rack 1 pieces
 Filter paper 1 piece

Materials
 Aquades sufficiently
 Ethanol 1,5 mL
 Ethylene glycol 0,5 mL
 Cyclohexanol 2 mL
 N-butyl alcohol 2 mL
 Tert-butyl alcohol 1,5 mL
 Phenol 2,5 mL
 NaOH 10% 20 drops
 Naphtol 0,5 mL
 1-propanol 1 mL
 2-propanol 1,5 mL
 O-cresol 1 mL
 Phenolphtalein 12 drops
 Sodium metal sufficiently
 Lucas reagent 20 drops
 2-butanol 1 mL
 Bromine water 1 mL
 FeCl3 5% 2 mL
 Resorcinol 2 drops
 KMnO4 1,5 mL
 CH3COOH 2,5 mL
 CH3COONa 10% 2,5 mL
 K4FeCN6 5 drops
G. PROCEDURES
1. Solubility

0,5 mL 0,5 mL 0,5 mL

0,5 mL 0,5 mL 0,5 mL
of of n- of tert-
of of cyclo- of
etylene butyl butyl
ethanol hexanol phenol
glycol alcohol alcohol

Put into Put into Put into Put into Put into Put into
Test tube Test tube Test tube Test tube Test tube Test tube
1 2 3 4 5 6
Added 2 Added 2 Added 2 Added 2 Added 2 Added 2
mL of mL of mL of mL of mL of mL of
distilled distilled distilled distilled distilled distilled
water water water water water water
Shaked Shaked Shaked Shaked Shaked Shaked

Result Result Result Result Result Result

Reaction:
 Test tube 1
C2H5OH (aq) + H2O (l)  C2H5OH (aq)
 Test tube 2
C2H6O2 (aq) + H2O (l)  C2H6O2 (aq)
 Test tube 3

(aq) + H2O (l) 

 Test tube 4
CH3CH2CH2CH2OH (aq) + H2O (l)  CH3CH2CH2CH2OH (aq)
 Test tube 5
 (aq) + H2O (l)  (aq)
 Test tube 6

(aq) + H2O (l) 

2. Reaction with Alkali

0,5 mL of 0,5 mL of 0,5 mL of 0,5 mL of

n-butyl alcohol cyclohexanol phenol naphtol
Put into test tube Put into test Put into test Put into test
tube 1 tube 2 tube 3 tube 4
Added 5 mL of Added 5 mL of Added 5 mL of Added 5 mL
NaOH NaOH NaOH NaOH
Shaked Shaked Shaked Shaked

Result Result Result Result

Reaction:
 Test tube 1
CH3CH2CH2CH2OH (aq) + NaOH (aq) 
 Test tube 2

(aq) + NaOH (aq) 

 Test tube 3
 (aq) + NaOH (aq)  (aq) + H2O (l)
 Test tube 4

(aq) + NaOH (aq)  (aq) + H2O (l)

3. Reaction with Sodium Metal

1 mL of 1 mL of 1 mL of 1 mL of
ethanol 1-propanol 2-propanol o-cresol
Put into test Put into test Put into test Put into test
tube 1 tube 2 tube 3 tube 4
Added Added Added Added 3 drops
3 drops of 3 drops of 3 drops of of PP
PP indicator PP indicator PP indicator indicator
Added a Added a Added a Added a
small of small of small of small of
sodium metal sodium metal sodium metal sodium metal

Result Result Result Result

Reaction:
 Test tube 1
2CH3CH2OH (aq) + 2Na (s)  2CH3CH2ONa (aq) + H2O (l)
 Test tube 2
2CH3CH2CH2OH (aq) + 2Na (s)  2CH3CH2CH2ONa (aq) +
H2 (g)
 Test tube 3
 2CH3CH(OH)CH3 (aq) + Na (s)  2CH3CH(ONa)CH3 (aq) +
H2 (g)
 Test tube 4

(aq) + Na (s)  (aq)

+ H2 (g)

4. Lucas Testing

1 mL of 1 mL of 1 mL of 1 mL of
1-butanol 2-butanol cyclohexanol Tert-butyl alcohol
Put into test Put into test Put into test Put into test tube 4
tube 1 tube 2 tube 3
Added Added Added Added 5 drops of
5 drops of 5 drops of 5 drops of 5 drops of Lucas
Lucas reagent Lucas reagent Lucas reagent reagen
Don't shake it Don't shake it Don't shake it Don't shake it and
and note the and note the and note the and note the time
time taken for time taken for time taken for taken for the mixture
the mixture the mixture the mixture become turbid or
become become become separate into two
turbid or turbid or turbid or layers
separate into separate into separate into
two layers two layers two layers

Result Result Result Result

Reaction:
 Test tube 1
ZnCl2
CH3CH2CH2CH2OH (aq) + HCl (aq)  CH3CH2Cl (aq) + H2O (l)
  Test tube 2
ZnCl2
CH3CH2CH(OH)CH3 (aq) + HCl (aq)  CH3CH2CH(Cl)CH3 (aq)
 Test tube 3

ZnCl2
(aq) + HCl (aq)  (aq) + H2O (l)
 Test tube 4

ZnCl2
(aq) + HCl (aq)  (aq) +
H2O (l)

5. The Reaction of Phenol with Bromine Water

1 mL of phenol
Put into test tube
Added 1 mL of bromine water
Shaked until no discoloration of yellow color
Observed and noted

Result

Reaction:

(aq) + 3Br2 (aq)  (aq) + 3HBr (aq)

6. The Reaction of Phenol with Iron(III) Chloride

2 drops of phenol 2 drops of resorcinol 2 drops of 2-propanol

Put into test tube Put into test tube Put into test tube

Added 5 mL of Added 5 mL of Added 5 mL of

distilled water distilled water distilled water
Added 2 drops of Added 2 drops of Added 2 drops of
FeCl3 5% FeCl3 5% FeCl3 5%
Shaked Shaked Shaked

Result Result Result

Reaction:
 Test tube 1

 Test tube 2

 Test tube 3
CH3CH(OH)CH3 (aq) + FeCl3 (aq) 
7. Identification of functional groups of carboxylic
2,5 mL of acetic
acid

Added into test tube

Added 1,5 mL of 1 N KMnO4 solution
Observed the changes

Result

Reaction:
CH3COOH (aq) + 2MnO4- (aq)  3CO2 (g) + 2MnO2 (s) + 2OH- (aq) +
2H2O (l)

2,5 mL of
CH3COONa 10%
Added into test tube
Added 1,5 mL of FeCl3 5% solution
Heated until appear red brownish color
Filtered

Residue Filtrate
Added 5 drops of K4FeCN6
Compared the color result of theexperiment
with ferric chloride with the same amount

Result

Reaction:
 CH3COONa (aq) + FeCl3 (aq)  CH3COO- (aq) + NaCl (aq) +
Fe3+ (aq)
 CH3COO- (aq) + Fe3+ (aq) + 2H2O (l)  [Fe(OH)2(CH3COO)6]+
(aq) + 2H+ (aq)
 [Fe(OH)2(CH3COO)6]+ (aq) + 4H2O (l)  3Fe(OH)2CH3COO (s) +
3CH3COOH (aq) + 3H+ (aq)
H. RESULT OF OBSERVATION

Observation Results
No. Procedure Hypothesis/Reaction Conclusion
Before After
1. Solubility  ethanol  Test tube 1: Reaction  Solubility level
colorless ethanol + H2O  Test tube 1 ethylene glycol >
solution  soluted C2H5OH(aq) + ethanol > tertiary
 ethylene  Test tube 2: H2O(l)  butyl alcohol > n-
glycol ethylene C2H5OH(aq) butanol > phenol >
colorless glycol  C2H6O2(aq) + cyclohexanol
solution + H2O  H2O(l)  C2H6O2  The longer the
 cyclohexano soluted (aq) chain carbon in
l  Test tube 3:  Test tube 3: alcohol, so its
colorless cyclohexanol solubility will get
solution + H2O  smaller
 n-butyl become two  The more
alcohol layer branches, the
colorless  Test tube 4: greater solubility
(aq) +
solution  Alleyclic alcohol
n-butyl H2O(l) 
 Observation Results
No. Procedure Hypothesis/Reaction Conclusion
Before After
 ter-butyl alcohol  Test tube 4: has solubility the
alcohol + H2O  CH3CH2CH2CH2O greater one
colorless soluted H(aq) + H2O(l)  compared to cyclic
solution  Test tube 5: CH3CH2CH2CH2O alcohol
 phenol ter-butyl H(aq)  Unsurated cyclic
yellowish alcohol + H2O  Test tube 5: alcohol has greater
orange  soluted CH3 solubility than
solution  Test tube 6: cyclic alcohol
3HC C OH
 water phenol + H2O
CH3
colorless  become
(aq) + H2O (l) 
solution two layer
CH3

3HC C OH

CH3
(aq)
 Test tube 6:
 Observation Results
No. Procedure Hypothesis/Reaction Conclusion
Before After

(aq) +
H2O(l) 
2. Reaction with Alkali  n-butyl  Test tube 1: Reaction:  Compound that
alcohol n-butyl  Test tube 1: can react with
colorless alcohol CH3CH2CH2CH2O alkali (NaOH) is
solution + NaOH  H(aq) + NaOH(aq) naphtol and
 cyclohexano appear bubles,  phenol
l colorless  Test tube 2:  Compund that
colorless become two can't react perfect
solution layer with alkali
 NaOH 10%  Test tube 2: (NaOH) is alcohol
colorless cyclohexanol and cyclohexanol
 Observation Results
No. Procedure Hypothesis/Reaction Conclusion
Before After
solution + NaOH 
 phenol appear bubles,
yellowish colorless
orange become two
solution layer (aq) +
 naphtol  Test tube 3: NaOH(aq) 
brownish phenol +  Test tube 3:
orange solid NaOH 
solution colorless
solution
 Test tube 4:
naphtol (aq) +
+ NaOH  NaOH(aq) 
yellowish
solution
 Observation Results
No. Procedure Hypothesis/Reaction Conclusion
Before After

(aq) +
H2O(l)
 Tet tube 4:

(aq) +
NaOH(aq) 

(aq) +
H2O (l)
 Observation Results
No. Procedure Hypothesis/Reaction Conclusion
Before After
3. Reaction with Sodium Metal  ethanol  Test tube 1: Reaction - All compound
colorless ethanol + PP  Test tube 1: alcohol if reacted
solution  colorless 2CH3CH2OH (aq) + with sodium metal
 indicator PP solution 2Na (s)  will produce salt
colorless ethanol + PP 2CH3CH2ONa (aq) + sodium alcoxide and
solution + Na  H2(g) H2 gas
 metal purple bubbly  Test tube 2: - The change of the
sodium solution, after 2CH3CH2CH2OH (aq) color from colorless
white color, a while purple + 2Na (s)  to purple indicates
solid still purple 2CH3CH2CH2ONa(aq the occurrence of

 1-propanol Purple ) + H2 (g) reactions that

colorless solution (+++)  Test tube 3: indicates the

solution  Test tube 2: 2CH3CH(OH)CH3 (aq) presence of alcohol

 and phenol that
2-propanol 1-propanol + Na (s) 
colorless + PP  contain hydroxyl
2CH3CH(ONa)CH3
solution colorless functional group
(aq) + H2 (g)
 Observation Results
No. Procedure Hypothesis/Reaction Conclusion
Before After
 O-cresol solution  Test tube 4:
colorless 1-propanol +
solution PP + Na 
purple bubbly
solution, after
a while purple (aq) + Na (s) 
fades
Purple
solution (++)
 Test tube 3:
2-propanol
(aq) + H2 (g)
+ PP 
colorless
solution
2-propanol +
PP + Na 
 Observation Results
No. Procedure Hypothesis/Reaction Conclusion
Before After
purple bubbly
solution,
Purple
solution (+)
 Test tube 4:
O-kresol + PP
 colorless
solution
O-cresol + PP
+ Na 
purple bubbly
solution,
Purple
solution
(++++)
4. Lucas Testing  Lucas  Test tube 1: Reaction - primary alcohol
colorless 1-butanol  Test tube 1: type, secondary,
 Observation Results
No. Procedure Hypothesis/Reaction Conclusion
Before After
solution + Lucas CH3CH2CH2CH2OH(a tertianary or cyclic
ZnCl2
 1-butanol  colorless q) + HCl (aq)  alcohol can be done
colorless solution CH3CH2Cl (aq) + H2O with lucas besed test
solution Time : 10 (g) difference formation
 2-butanol minutes  Test tube 2: of depent (murky)
colorless  Test tube 2: CH3CH2CH(OH)CH3
solution 2-butanol (aq) + HCl (aq) 
 cyclohexano + Lucas CH3CH2CH(Cl)CH3
l  colorless (aq)
colorless solution  Test tube 3:
solution Time : 10
 ter-butyl minutes
alcohol  Test tube 3:
colorless cyclohexanol
solution + Lucas (aq) + HCl
 colorless
solution
 Observation Results
No. Procedure Hypothesis/Reaction Conclusion
Before After
Time : 10
minutes
 Test tube 4:
ter-butyl
alcohol + (aq) 
Lucas (aq) + H2O (l)
 colorless Test tube 4:
solution
Time : 1,5
minutes

ZnCl2
(aq) + HCl (aq) 

(aq) + H2O (l)

 Observation Results
No. Procedure Hypothesis/Reaction Conclusion
Before After
5. The Reaction of Phenol with Bromine  bromine  bromine water Reaction: - phenol can react
Water water : + phenol  with bromine water
yellow yellow because proven by
transparant solution the color of the
 phenol solution changes to
yellowish (aq) + yellow
orange 3Br2 (aq) 
solution

(aq) + 3HBr (aq)

6. The Reaction of Phenol with Iron(III)  resorcinol =  Test tube 1: Reaction - phenol and
Chloride yellow Phenol + H2O Test tube 1: resorcinol can reacts
solution  colorless with Fe3+ ion form a
 Observation Results
No. Procedure Hypothesis/Reaction Conclusion
Before After
 phenol solution complex compound
yellowish Phenol + H2O marted by color
orange + FeCl3  change solution
solution purple Test tube 2: - 2-propanol does
 2-propanol solution (+++) not react with FeCl3
colorless  Test tube 2:
solution resorcinol + Test tube 3:
 FeCl3 5% H2O  CH3CH(OH)CH3 (aq)
yellowish colorless + FeCl3 (aq) 
solution solution
resorcinol +
H2O + FeCl3
 faded
purple
solution (++)
 Test tube 3:
2-propanol +
 Observation Results
No. Procedure Hypothesis/Reaction Conclusion
Before After
H2O 
colorless
solution
2-propanol +
H2O + FeCl3
faded
purple
solution
7.
2,5 mL acetic acid  CH3COOH,  CH3COOH + CH3COOH + 2MnO4- Carboxylic
colorless KMnO4, (aq) 3CO2(g) + functional group can
- Added into the test tube
solution purple 2MnO2(s) + 2OH-(aq) be identified by
- Added 1,5 mL of KMnO4 1 N
solution  KMnO4, 1 solution, + 2H2O(l) formic acid oxidized
- Observed the changes N, purple appear dark by KMnO4 which is
solution purple (petunjuk praktikum, needed by the purple
Result color and dark
precipitate, 2020).
appear gas purple precipitate
CO2
 Observation Results
No. Procedure Hypothesis/Reaction Conclusion
Before After
8.  CH3COONa,  CH3COONa + CH3COONa(aq) + Complex reactions
2,5 mL CH3COONa
colorless FeCl3, red FeCl3(aq) occur in filtrate and
- Added into the test tube CH3COO-(aq) + formed red-brown
solution solution
- Added 1,5 mL FeCl3 5%
solution until become red  FeCl3 5%,  CH3CONa + NaCl(aq) + Fe3+(aq) base of iron (III)
- Heated until appear red yellowish FeCl3 and the base which identifies
brownish color
solution heated, there CH3COO-(aq) + the presence of a
- filtered
 K4FeCN6, are residue Fe3+(aq) + 2H2O(l) carboxyl functional
yellow and filtrate [Fe(OH)2(CH3COO)6] group
+
solution  Residue, (aq) + 2H+(aq)
residue Filtrate
orange
- Added K4FeCN6
5 drops presipitate
- Compared the  Filtrate , [Fe(OH)2(CH3COO)6]
color result of the +
(aq) + 4H2O(l)
colorless
experiment with
ferric chloride solution 3Fe(OH)2CH3COO(s)
with the same  Filtrate + + 3CH3COOH(aq) +
amount
K4FeCN6, 3H+(aq)
Result yellow
 Observation Results
No. Procedure Hypothesis/Reaction Conclusion
Before After
greenish Deep red staining,
solution caused by the
 FeCl3 + formation of complex
K4FeCN6, ions
dark blue [Fe(OH)2(CH3COO)6]
+
solution . by boiling the red
solution, it breaks
down and red-brown
base of iron (III) base
is formed (Svehla,
1985).
I. ANALYSIS AND EXPLANATION
The purpose of Alcohol dan Phenol experiment is to to distinguish the
properties between alcohol and phenol and to know the types of reactions and
reagents that can be used to distinguish between alcohol and phenol
compounds. And the purpose of Carboxylic experiment is to identify organic
compounds that contain functional groups of carboxylic.
1. Solubility
The purpose of the first procedure is to distinguish between alcohol
and phenol compounds by its solubility. Six test tube were prepared and
named as test tube 1, test tube 2, test tube 3, test tube 4, test tube 5, and
test tube 6.
In the first test tube, we put 0,5 mL of ethanol (colorless solution).
Ethanol is an alcohol because ethanol has a hydroxyl functional groups.

After added 0,5 mL of ethanol, we added 2 mL of distilled water or

aquades. The purpose of addition of aquades is to know the solubility of
ethanol in water. After we added 2 mL of water, we shaked the test tube
to make the solution mixed. And the result is ethanol solution become
colorless and has one phase. It indicated that ethanol is dissolved in
water. The reaction is:
C2H5OH (aq) + H2O (l)  C2H5OH (aq)
In the second test tube, we put 0,5 mL of ethylene glycol (colorless
solution). Ethylene glycol (ethane-1,2-diol) is an alcohol because
ethylene glycol has two hydroxyl functional groups.

After added 0,5 mL of ethylene glycol, we added 2 mL of distilled

water (aquades). The purpose of addition of aquades is to know the
solubility of ethylene glycol in water. After we added 2 mL of water,
we shaked the test tube to make the solution mixed. The result is
ethylene glycol solution become colorless and has one phase. It
indicated that ethylene glycol is dissloved in water. The reaction is:
 C2H6O2 (aq) + H2O (l)  C2H6O2 (aq)
In the third test tube, we added 0,5 mL cyclohexanol (colorless
solution). Cyclohexanol is an alcohol because cyclohexanol has a
hydroxyl functional groups.

After added 0,5 mL of cyclohexanol, we added 2 mL of distilled water

(aquades). The purpose of addition of aquades is to know the solubility
of cyclohexanol in water. After we added 2 mL of water, we shaked the
test tube to make the solution mixed. The result is cyclohexanol
solution separated into two layers. It indicated that cyclohexanol is
insoluble in water. The reaction is:

(aq) + H2O (l) 

In the test tube number four, we put 0,5 mL of n-butyl alcohol (1-
butanol). N-butyl alcohol (colorless solution) has one hydroxyl
functional groups which is bounded on the first C atom of parents
chain.

After added 0,5 mL of n-butyl alcohol, we added 2 mL of distilled

water (aquades). The purpose of addition of aquades is to know the
solubility of n-butyl alcohol in water. After we added 2 mL of water,
we shaked the test tube to make the solution mixed. The result is n-
butyl alcohol become colorless and has one phase. It indicated that n-
butyl alcohol is dissolved in water. The reaction is:
CH3CH2CH2CH2OH (aq) + H2O (l)  CH3CH2CH2CH2OH (aq)
 The fifth test tube, we put 0,5 mL of tert-butyl alcohol (colorless
solution). Tert-butyl alcohol has one hydroxyl functional groups.

After we added 0,5 mL of tert-butyl alcohol, into the test tube, we

added 2 mL of distilled water (aquades) to know the solubility tert-butyl
alcohol in water. And the result is ter-butyl alcohol become colorless
and has one phase. It indicated that tert-butyl alcohol is diddolved in
water. The reaction is:

(aq) + H2O (l)  (aq)

In the last test tube or test tube 6, we put 0,5 mL of phenol
(yellowish solution). Phenol is the aromatic compounds that has
hydroxyl functional groups.

After we added 0,5 mL of phenol into the test tube, we added 2 mL of

distilled water (aquades). The purpose of the addition of aquades is to
know the solubility of phenol in water. The result is phenol solution
separated into two layers. It indicated that phenol is insoluble in water.
The reaction is:
 (aq) + H2O (l) 
Based on theory, All alcohols are generally soluble in water
because they can form hydrogen bonds with water. So that alcohol more
soluble than phenol. The solubility of ethylene glycol is greatest
because ethylene glycol has more -OH groups. The more -OH groups,
the more easily soluble in water because hydrogen bonds formed more.
The second is ethanol, because ethanol has the shortest parents chain,
and then tert-butyl alcohol because tert-butyl has more branches
although it has 4 C atoms and the next is n-butyl alcohol. Solubility of
n-butyl alcohol is lower than tert-butyl alcohol because n-butyl alcohol
has a straight hydrocarbon chain (parents chain).
The solubility of the 6 compounds from the largest to the smallest
are: ethylene glycol > ethanol > tert-butyl alcohol > n-butyl alcohol >
phenol > cyclohexanol
2. Reaction with Alkali
The purpose of reaction with alkali experiment is to determine the
types of reactions and reagents that can be used to distinguish between
alcohol and phenol compounds. In this experiment the reagents that we
used is NaOH solutions which were of a strong base so we could find
out the acidity properties of alcohol and phenol by reacting it.
The first step is prepared 4 test tube and numbered every test tube
as test tube 1, test tube 2, test tube 3, and test tube 4. The next step is
put n-butyl alcohol into test tube 1, cyclohexanol into test tube 2,
phenol into the third test tube, and naphtol into the las test tube.
In the first test tube, we put 0,5 mL of n-butyl alcohol. N-butyl
alcohol is a colorless solution that has one hydroxil functional groups
and has 4 C atom in the parents chain.
 In the second test tube, we put 0,5 mL of cyclohexanol.
Cyclohexanol is a colorless solution that has cyclic chain and one
hydroxyl functional groups.
In the third test tube, we put 0,5 mL of phenol. Phenol is a orange
yellowish solution. Phenol is an aromatic compounds that has one
hydroxyl functional groups.
In the last test tube, we put naphtol. Naphtol is a solid that has
orange brownish color. To make the naphtol solution, we added a little
of naphtol solid into the test tube and added 0,5 mL of aquades.
The next step is added 5 mL of NaOH 10%. Before that, we
measured the NaOH solution with 10 mL graduated cyllinder. To
measure the solution, we took the NaOH solution from the reagent
bottle with pipette. After that, we put into the graduated cyllinder drop
by drop until it close to the scale of 5 mL. Be careful to drop the
solution if it start to close the scale of 5 mL. Look at the meniscus
border. Make sure that the lower arches on the meniscus are straight
with the scale of 5 mL and we must see them parallel to our eyes.
The next step is shaked the test tube and the result is in the test
tube 1, there are formed bubbles, colorless and separated into two
layers. It can be indicated that n-butyl alcohol not react with NaOH. It
also occur in the test tube 2 that contain cyclohexanol. In the test tube 2,
formed bubbles and separated into two layers. It also indicated that
cyclohexanol can't react with NaOH.
A different result happen in the third and fourth test tube. In the
third test tube contain phenol and the fourth test tube contain naphtol.
The third test tube become colorless and has one phase. And the fourth
test tube become yellowish solution. This indicated that phenol and
naphtol is react with NaOH. The reaction is:
Test tube 3
 (aq) + NaOH (aq)  (aq) + H2O (l)
Test tube 4

(aq) + NaOH (aq)  (aq) + H2O (l)

Alcohol has a low acidity and tend to be neutral, and when alcohol
react with NaOH which is an alkaline, there is no reaction. So that n-
butyl alcohol and cyclohexanol can't reacted with NaOH.
Phenol is reacted because phenol has a high acidity than alcohol, so
when phenol react with NaOH, reaction will occur. Phenol has a higher
acidity because the phenoxy anion is stabilized by the presence of
resonance and phenol can release hydrogen ions to form phenoxide.
NaOH solution will make the deprotonated phenol and produce
phenoxide ions and making H atoms substituted with Sodium from
Sodium Hydroxide. This result also occur when react naphtol and
NaOH.
3. Reaction with Sodium
The third experiment is reaction with sodium metal. The purpose
of this experiment is to know the acidity level of an alcohol by reacting
it with Alkali Metal (Sodium).
The first step is prepared 4 test tube and numbered as test tube 1,
test tube 2, test tube 3, and test tube 4. In the first test tube, we put 1 mL
of ethanol (colorless solution). The second test tube is added with 1 mL
of 1-propanol (colorless solution). The third test tube is added with 1
mL of 2-propanol (colorless solution). And the last test tube is added
with 1 mL of o-cresol (colorless sodium).
 Next step is added 3 drops of phenolphtalein indicator (colorless
solution) into all test tube. After added PP indicator, we took a small
piece of sodium metal and put into the test tube.
In the first test tube, the solution become purple (+++) and there
are bubbles. The reaction is:
2CH3CH2OH (aq) + 2Na (s)  2CH3CH2ONa (aq) + H2O (l)
In the second test tube, the solution becomepurple (++) and there
are bubbles. The reaction is:
2CH3CH2CH2OH (aq) + 2Na (s)  2CH3CH2CH2ONa (aq) + H2 (g)
In the third test tube, the solution become purple bubbly solution (+).
The reaction that occur is:
2CH3CH(OH)CH3 (aq) + Na (s)  2CH3CH(ONa)CH3 (aq) + H2 (g)
In the last test tube that contain o-cresol, the solution become purple
bubbly solution (++++). The reaction is:

(aq) + Na (s)  (aq) + H2 (g)

An alkoxide is a salt of an alcohol. The alkoxide is a strong base,
generally stronger than hydroxide. to make an alkoxide from an alcohol,
a base which is stronger than the alkoxide itself is required. The easiest
method for making alkoxides is reacting alcohol with an alkali metal,
such as sodium and potassium.
The reaction is not the acid-base reaction, but the oxidation-
reduction reaction. Sodium metal is oxidized into a cation, and
hydrogen from the -OH group is reduced to hydrogen gas. Used sodium
metal because the reacted carbon chain is less than four which is
sufficiently reactive if reacted with alcohol. A more reactive metal is
used if the number of carbon atoms to be reacted ≤ four. The reaction
with the alkali metal increases the alkalinity of ethoxide so that
phenolphtalein changes color to pink which indicates an increase in pH
4. Lucas Testing
 The next experiment is Lucas testing. The purpose of this
experiment is to determine the kinds of alcohol, whether classified as
primary, secondary, or tertiary alcohol by reacting with Lucas Reagents.
Lucas reagent is a mixture between concentrated chloride acid and
ZnCl2.
In the first test tube, we put 1 mL of 1-butanol. The second test
tube is added with 1 mL of 2-butanol. The third is added with 1 mL of
cyclohexanol. And the fourth test tube is added with 1 mL of tert-butyl
alcohol. After that, we added 5 drops of Lucas reagent into the first test
tube and turn on the stopwatch to note the time needed to the solution
become turbid or separated into two layers. The addition of Lucas
reagent is done one by one per test tube because we need to record the
time and observed every reaction that happen in the test tube. Don't
shake the test tube, so that we put the test tube in the test tube rack.
In the test tube 1 that contain 1-butanol, after the addition of Lucas
reagent and waited until 10 minutes, there is no changes in the solution.
The solution is still colorless. It also happen in the second test tube and
third test tube that contain 2-butanol (test tube 2) and cyclohexanol (test
tube 3). The reaction is:
Test tube 1
ZnCl2
CH3CH2CH2CH2OH (aq) + HCl (aq)  CH3CH2Cl (aq) + H2O (l)
Test tube 2
ZnCl2
CH3CH2CH(OH)CH3 (aq) + HCl (aq)  CH3CH2CH(Cl)CH3 (aq)
Test tube 3

ZnCl2
(aq) + HCl (aq)  (aq) + H2O (l)
But in the last test tube that contain tert-butyl alcohol the solution
formed a crystal but if we shaked it although it is a slow shake, the
crystal is gone and dissolved. The reaction is:
 (aq) + HCl (aq) ZnCl
2 (aq) + H2O (l)
In theory it is explained that if alcohol is reacted with Lucas
reagents it takes a very long time to separate into two layers is the
primary alcohol. Alcohol is reacted with Lucas reagents it takes a very
short time to separate the solution into two layers or turbidity is a
tertiary alcohol. The primary alcohol is less reactive, requiring the help
of aqueous ZnCl2 as a catalyst, in order to react with HCl, in order for
the time required to react more quickly. ZnCl2 increases the
concentration of chloride ions, thus accelerating the reaction at SN2.
The role of ZnCl2 is similar to the role of H+. A non-aqueous ZnCl2 is a
very powerful lewis acid with empty orbitals that can accept electron
pairs of oxygen. The formation of a complex between ZnCl2 and
alcohol oxygen weakens the C-O bond which increases the oxygen
group's ability to go.
5. The Reaction of Phenol with Bromine Water
The fifth experiment is reaction of phenol with bromine water. The
purpose of this experimrnt is to identify the solution is a phenol or not.
The solvents used is bromwater. The purpose of bromwater is to do
substitution reactions that will replace the hydrogen atoms in phenol.
The first step is put 1 mL of phenol (orange solution) into test tube
and then added 1 mL of bromine water (yellow solution) and shaked
until the yellow color is not change.
Bromwater do substitution reaction that will replace the hydrogen
atoms in phenol. The color of the solution become yellow shows that
there has been a substitution reaction between phenol and Br2. The
hydroxy group of phenols make benzene ring reactive to the
electrophilic substitution.
The hydroxyl group is a group that can deactivate the benzene
nucleus and the ortho-para direct. Thus, the hydroxy group (-OH) may
attract another group, example Br to attach to the benzene group that is
 in the ortho and para. Bromo enters in the ortho position due to
resonance in the aromatic ring of phenol. The reaction is:

(aq) + 3Br2 (aq)  (aq) + 3HBr (aq)

6. The Reaction of Phenol with Iron(III) Chloride
The sixth experiment is the reaction of phenol with FeCl3 or
iron(III) chloride. The purpose of this experiment is to detect the
presence of phenol in the sample with the addition of a ferric chloride
solution.
The first step is prepared 3 test tube and named as test tube 1, test
tube 2, and test tube 3. All test tube is added with 5 mL of aquades or
distilled water.
In the test tube number 1, weput two drops of phenol (orange
solution), and the second test tube, we put two drops of resorcinol
(yellow solution), and the third test tube is added with two drops of 2-
propanol (colorless solution). And then the next step is added two drops
of iron(III) chloride solution (yellowish solution) into all test tube.
Into the first tube is poured 2 drops of phenol. After that, added 2
drops of yellow FeCl3 solution, causing the color of the solution in the
tube change into a dark purple solution (+++). The reaction is:
 Reaction the ferric chloride test is a substitution reaction between
the sample and the ferric chloride reagent in which H+ in phenol is
replaced with Fe3+ with a ferric chloride reagent. While the lose H+
binds to Cl- form HCl. While Fe3+ will bind to the benzene ring forming
FeO which can change the color from transparent to light brown,
indicating positive test results.
In the third test tube is added 2 drops of resorcinol, then added 2
drops FeCl3 produced faded purple solution (++). The color change
indicates the formation of complex compounds. The reaction is:

In the third test tube is added 2 drops of 2-propanol that in

colorless solution, and added 1-2 drops of yellow FeCl3, resulting in a
yellow solution. This indicates that 2-propanol does not react with ferric
chloride.
CH3CH(OH)CH3 (aq) + FeCl3 (aq) 
7. Carboxylic Acids
The last experiment of this title is carboxylic acid. The purpose of
this experiment is to identify the carboxylic functional groups that
contain in organic compounds.
The first procedure is measuring 2,5 mL of acetic acid (colorless
solution) then put into test tube. After that, added 1,5 mL of 1N KMnO4
solution (purple solution). Then observed the changes that occur.
The addition of KMnO4 is to oxydized acetic acid. KMnO4 is reactant
that easily obtained, cheap, and does not required an indicator. When
acetic acid react with KMnO4, there are dark purple precipitate in the
solutions. The reaction is:
 CH3COOH (aq) + 2MnO4- (aq)  3CO2 (g) + 2MnO2 (s) + 2OH- (aq) +
2H2O (l)
In the second procedure, the first step is measuring 2,5 mL of
CH3COONa 10% then put into test tube. After that, added 1,5 mL of
FeCl3 5% until the solution become red color. Then heated the solution
until there are brownish precipitate. Then filtered the residue with filter
paper. The filtrate is put into test tube and added 5 drops of K4FeCN6
and then compared with ferric chloride in the same amount. The
reaction is:
 CH3COONa (aq) + FeCl3 (aq)  CH3COO- (aq) + NaCl (aq) +
Fe3+ (aq)
 CH3COO- (aq) + Fe3+ (aq) + 2H2O (l)  [Fe(OH)2(CH3COO)6]+
(aq) + 2H+ (aq)
 [Fe(OH)2(CH3COO)6]+ (aq) + 4H2O (l)  3Fe(OH)2CH3COO (s) +
3CH3COOH (aq) + 3H+ (aq)
Complex reactions occur in filtrate and formed a red-brown base of
iron(III) base which is identified that acetic acid and CH3COONa
classified in the carboxylic groups.
J. CONCLUSION
After we done the experiment of Alcohol, Phenol, and Carboxylic Acid,
we can conclude that,
1. Solubility
- The longer the chain carbon of alcohol, so its solubility will get
smaller
- The more branches, the greater the solubility
- Alicyclic alcohol has the greatest solubility compared with cyclic
alcohol
- Unsaturated cyclic alcohol has greater solubility than cyclic alcohol
2. Reaction with alkali
- Compound that can react with alkali (NaOH) is classified as phenol
and alcohol does not react with alkali
3. Reaction with sodium metal
 - All alcohol compounds if reacted with sodium metal will produce
alkoxide (salt from alcohol)
- The change of color from colorless to purple indicates the occurence
of reaction that indicated the presence of alcohol and phenol which is
contain hydroxyl groups
4. Lucas testing
- Primary, secondary, and tertiary alcohol can be identified with Lucas
reagent based on the difference formation of precipitate.
5. Reaction with bromwater
- Phenol can react with bromwater, proven by the color of the solution
changes turn yellow
6. Reaction with iron(III) chloride
- Phenol and resorcinol can react with Fe3+ ions form a complex
compounds
- 2-propanol does not react with FeCl3
7. Crboxylic acids
- Carboxyl functional groups can be identified by acetic acid oxidized
by KMnO4
- Complex reaction occur in filtrate and formed a red-brown base of
iron(III) base which identifies the presence of a carboxyl functional
groups
K. REFERENCES
Brady, J. E. 1999. Kimia Universitas : Asas & Struktur. Jakarta: Binarupa
Aksara
Carey, F. A. 2000. Organic chemistry 4th ed. USA: McGraw-Hill
Daintith, J. 1990. Kamus Lengkap Kimia. Jakarta: Erlangga
Fessenden, R . J and Fessenden, J. S. 1986. Organic Chemistry 3rd ed. Jakarta:
Erlangga
Hart, Harold et al. 2003. Kimia Organik. Jakarta: Penerbit Erlangga
Solomons, T. W. G. and Fryhle, C. B. 2011. Organic Chemistry, 10th ed. New
Jersey: John Wiley & Sons, Inc
L. ATTACHMENTS
a. Answer of questions
1. Which of 1-pentanol and 1-heptanol is more difficult to dissolve in
water? Explain
Answer:
 The shorter the C chain, the easier it dissolves in water because
hydroxy groups can form hydrogen bonds with water molecules.
 Pentanol is more soluble than n-heptanol because the carbon
chain in n-heptanol is longer than pentanol so it reduces its
solubility to water. in theory, shorter and more carbon chains will
be more soluble in water.
2. Write the reaction equation that shows the solubility of the phenoll in
the dissolution of 10% sodium hydroxide!
Answer:

+ NaOH  + H2 O
3. From the results of the experiments above, which ones are more
acidic, n-hexanol or phenol? Explain the reason!
Answer:
Phenol is more acidic than n-hexanol because the OH group in phenol is
+
bound to the aromatic cyclic chain so phenol can release H when
reacted with NaOH, because the acidity of phenol is higher than alcohol.
Alcoholic compounds that have low acidity cannot react with NaOH.
4. Write the equation for the reaction between ethanol and sodium! Did
the instructions say the results of this reaction?
Answer:
C2H5OH (aq) + Na (s)  C2H5ONa (aq) + H2 (g)

In the instructions there are no results from this reaction.

5. Based on the results of the experiment above, how can it be
distinguished between cyclohexanol and phenol?
 Answer:
Cyclohexanol cannot react with NaOH while phenol can react with
NaOH. This is because cyclohexanone is alcohol and alcohol cannot
form alkoxide salts with NaOH. While phenol can react with NaOH
because Phenol is a compound that is more acidic than alcohol and when
reacting with NaOH it can be converted into phenoxide anion which is a
weaker base than OH so that phenol will dissolve in alkaline solution as
phenoxide salt.
6. What is the effect of the Lucas reagent on each of the following
compounds: 1-butanol, cyclohexanol, and tert-butyl alcohol?
Answer:
Lucas reagent reacts quickly with tert-butyl alcohol (tertiary alcohol) by
forming insoluble alkyl chloride and arising as a cloudy suspension or as
a separate layer even without heating.While cyclohexanol (secondary
alcohol) reacts with Lucas reagent with a longer time compared to
tertiary butyl alcohol ± 11 minutes. While 1-butanol as primary alcohol
reacts slowly ± 15 minutes.
7. Among the following compounds: 1-butanol, triphenyl carbidol, and
resorcinol, which ones do not undergo oxidation in the Bordwell-
Wellman test?
Answer:
Primary and secondary alcohols can be easily oxidized by chromic acid,
while tertiary alcohols are not oxidized. So 1-butanol and resorcinol will
be oxidized, while triphenyl carbinol will not.
8. Write the equation for the reaction between phenol and bromine
water! Mention the types of reactions that occur!
Answer:
 + 3Br2 
(2,4,6-tribromophenol)
b. Documentation
A. Alcohol and phenol
1) Solubility

Phenol, yellowis solution Phenol + 2 ml of distilled water,

become two layers solution.

Etylen glicol, colorless solution. n-butyl alcohol, colorless

And then added 2 ml of distilled solution. And then added 2 ml
water, etylen glicol soluted. of distilled water, n-butyl
alcohol soluted.
 Ethanol, colorless solution. And Cyclohexanol, colorless
then added 2 ml of distilled solution. And then added 2 ml
water, ethanol soluted. of distilled water, the solution
become 2 layers.

Move from left to the right after added 2 ml of distilled water :

ethanol, etylen glicol, cyclohexanol, n-butyl alcohol, tertiary butyl
alcohol, phenol.
Cyclohexanol + 2 ml of distilled water become two layers. Phenol
+ 2 ml of distilled water become 2 layers. The rest of the sample
soluted.

2) Reaction with alkaly

 10% of sodium hidoxide 5 ml of 10% sodium hidroxide
solution solution. Colorless solution

substances to be tested Move Naphtol. Brownish orange

from left to the right : phenol, powder solid
naphtol, cyclohexanol, and n-
buthanol

Naphtol + 5 ml of 10% sodium Phenol + 5 ml of 10% sodium

hidroxide solution, Yellowish hidroxide solution, Colorless
solution. solution
 n-butyl alcohol + 5 ml of 10%
sodium hidroxide solution.
Become two layers

Move from left to the right : n-butyl alcohol, cyclohexanol, phenol,

and naphtol.
Cyclohexanol and n-butyl alcohol after added 5 ml of 10% sodium
hidroxide solution. Become two layers. The rest of the sample
reacted.

3) Reaction with sodium

 Phenolphthalein indicator. 2-propanol, Colorless solution.
Colorless solution And then added 3 drops of
Phenolphthalein indicator,
become colorless solution

1-propanol, Colorless solution.

And then added 3 drops of
Phenolphthalein indicator, become
colorless solution.
 Move from left to the right : ethanol, 1-propanol, 2-propanol, and o-
cresol.
Each sample after added 3 drops of Phenolphthalein indicator and a
small pieace of sodium become purple solution.

4) Lucas Testing

Form left to the right : tertiary butyl alcohol, cyclohexanol, 2-

butanol, 1-butanol. cyclohexanol, 2-butanol, 1-butanol after added
2 ml of lucas reagent and after the time is recorded up to 10
minutes there is no change. Tersier butyl alcohol after added 2 ml
of lucas reagent after a recorded time of up to 1.5 minutes a white
turbidity appears.

5) The reaction of phenol with bromine water

1 ml Phenol before added 1 ml 1 ml Phenol after added 1 ml of

 of bromine water : orange bromine water : yellow
transparant solution transparant solution

6) The reaction of phenol with Iron (III) Chloride

Phenol, orange solution Phenol added two drops of

FeCl3 solution, purple solution
(+++)

Resorsinol, yellwoish solution Resorsinol added two drops of

FeCl3 solution, purple solution
(++)
 2-propanol, colorless solution
Move from left to the right : 2-
propanol, resorsinol, and
phenol.
Phenol and resorsinol become
purple solution after added 2
drops of FeCl3. The purple of
phenol stronger than the
resorsinol’s.

B. Carboxylic acid
1) Carboxylic acid + KMnO4

Acetic acid, colorless solution. KMnO4, purple solution.

2,5 mL acetic acid + 1,5 mL KMnO4 solutin 1 N become purple
solution and appear dark purple precipitated.

2) CH3COONa + FeCl3
CH3COOna, colorless solution.
FeCl3, yellow solution.
2 mL of CH3COOna + 1,5 ml of
FeCl3 become red brownish
solution.
Filtrate, colorless solution
Filtrate, colorless solution
FeCl3, yellow solution
Red brownish solution heated,
and then appear red blob. And
after that filtered out.
Residue, red brownish
precipitated
Filtrate + K4FeCN6, yellow
greenish solution
 FeCl3, yellow solution

Filtrate, yellow greenish solution

FeCl3 + K4FeCN6, dark blue
solution