Ao-_e--EBg-A¥← CENTRO ESCOLAR UNIVERSITY – MANILA
DOCTOR OF DENTAL MEDICINE BATCH 2026
PCCH103L: ORGANIC CHEMISTRY (LABORATORY)
Mrs. Maria Kristina M. Salazar-Pascua
ADAPTED FROM: CEU LEAPS and Laboratory Manual
COURSE OUTLINE: 4th Block – 2nd Semester
1. Module 4: Unsaturated Hydrocarbon amd Properties
of Phenols
2. Module 5: Classification of Alcohols
3. Module 6: Carboxylic Acids and Amines
MODULE 4
INTRODUCTION
HYDROCARBONS
- are the simplest organic compounds that contain only
carbon and hydrogen.
- The majority of hydrocarbons are found naturally occur
in crude oil, where decomposed organic matter
provides an abundance of carbon and hydrogen which,
when bonded, can link to form seemingly limitless
chains.
- In terms of structure, they can be open chain (aliphatic)
or closed chain (cyclic) with the same empirical formula
but showing differences in properties. These
hydrocarbons can either be saturated or unsaturated.
- Being a major component of natural oil and gas,
Hydrocarbons undergo a very important reaction called
combustion which has a very important industrial
application.
are characterized by the presence of only
sigma (σ) bond; hence, the carbon atoms
are all single-bonded. These include the
alkanes (-C-) and the cycloalkanes.
Saturated hydrocarbons are generally inert
towards HCl and H2SO4. As well as
Saturated towards oxidizing agents like KMnO4 and
Hydrocarbons Na2Cr2O7 at room temperature. This is
due to the relative strength of the bonds in
the molecule. Generally, saturated
hydrocarbons are non-polar compounds
and do not react with ionic compounds
such as laboratory acids, bases, oxidizing
agents or reducing agents. But under the
presence of UV light or at very high
temperature, these compounds react with
Halogens (Br2 or Cl2) to yield halogenated
alkanes. This process is called substitution.
include alkenes (C=C) which contains at
least one pi bond (π) as well as alkynes,
cycloalkenes, cycloakynes and aromatic
compounds (contains benzene ring).
On the other hand, the characteristic
reactions of unsaturated hydrocarbons are
those that take place at the double bond
Unsaturated and this reaction is called addition.
Hydrocarbons Baeyer’s test is used to detect the degree
of unsaturation of alkenes and alkynes. For
aromatic compounds, they exhibit
resonance that results in conjugative
stability of the molecule. due to their pi
bonds in conjugation, they resist addition to
the pi bonds but readily undergo
substitution. This overall reaction is chiefly
called Electrophillic Aromatic Substitution.
CLASSIFICATION BASED ON THE NUMBER OF
CARBONS ATTACHED TO THE CENTRAL CARBON
A primary carbon is bonded to one other C.
A secondary carbon is bonded to two other C.
A tertiary carbon is bonded to three other C.
A quarternary carbon is bonded to four other C.
SATURATED HYDROCARBONS
• Contain only carbon-carbon single bonds.
• Each carbon in the hydrocarbon has the maximum
number of hydrogens bonded to it.
ALKANES (paraffins)
- Alkanes contain only single C-C and C-H bonds.
• Acyclic alkanes – contain chains of C atoms.
CnH2n+2
• Cycloalkanes – contain carbon atoms
arranged in a ring. CnH2n
Physical Properties:
➢ Alkanes contain only nonpolar C-C and C-H bonds.
➢ Major sources are natural gas and petroleum.
➢ Smaller alkanes are gases at room temperature,
whereas larger alkanes are liquids.
➢ Alkanes are insoluble in water.
• Soluble to non-polar organic compounds.
➢ Alkanes are less dense than water.
➢ Alkanes exhibit only weak inetrmolecular forces. '
• Van der waals or London Dispersion Force
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 ➢ Alkanes have low melting and boiling points. • It occurs when an alkane
• As the number of carbons in an alkane reacts with HNO3 to form a
increases, the boiling point increases. nitro alkane.
• As the number of carbons in an alkane • It occurs at a high
increasesm the intermolecular force becomes temperature (400 degrees
stronger. to 500 degrees celcius).
➢ Alkanes exhibit isomerism.
c. Sulphonation (SO3)
• It is the substitution reaction
of a hydrogen atom of an
alkane with -SO3H.
• A reaction with fuming
sulfuric acid (H2SO4) to give
alkanesulfonic acid.

Chemical Properties:
➢ Alkanes have no functional group, so they undergo
few reactions.

REACTION OF ALKANES
- Alkanes burn in the presence of O2
gas to form CO2 and H2O.
- It is an oxidation-reduction reaction.
a. Complete Combustion
• Takes place when there is
plenty of oxygen.
• Produces non-luminous
flame (blue flame).
Combustion • Products are CO2 and
water.

b. Incomplete Combustion
• Takes place when there is
limited oxygen.
• Produces luminous flame
(yellow flame).
• Products are CO2, CO, CO,
and water.
- Occurs when an exchange of
elements in the reactants takes
place.
a. Halogenation (Halogens)
• A substitution reaction that
occurs in the presence of
Substitiution light.
• Substitution of a single
hydrogen on the alkane for
a single halogen.
• It reacts with halogens
except I2.

b. Nitration (NO2)

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 UNSATURATED HYDROCARBONS ▪ If the reactant is an
asymmetrical alkene, two
• Consist of thre families of homologous compounds possible products can be
that contain multiple bonds between carbon atoms. formed in theory.
▪ Alkenes ▪ Markovnikov’s rule
▪ Alkynes o The H atom of H-X
▪ Arenes will bond to the
less substituted C
atom in the C=C
ALKENES (olefins) double bond.
- Alkenes are compounds that contain a carbon-carbon
double bond. CnH2n
o Acyclic alkenes – contain chains of C atoms
with double bonds but no rings. CnH2n
o Cycloalkenes – contain carbon atoms joined
in one or more rings with double bonds.
CnH2n-2

Physical Properties:
➢ Alkenes are insoluble in water.
➢ Alkenes are less dense than water.
➢ Alkenes have a lower melting point than that of an d. Hydration
alkane with the same number of carbon. ▪ The addition of water to an
alkene.
REACTION OF ALKENES ▪ Requires a strong acid,
H2SO4.
Combustio - Alkenes burn in the presence of O2 ▪ The product formed by
n gas to form CO2 and H2O. hydration is an alcohol.
- New groups X and Y are added to the ▪ If the reactant is an
alkene. asymmetical alkene, the
- One bond of the double bond is product will be determined
broken and two new single bonds are by Markovnikov’s rule.
formed.
a. Hydrogenation
▪ The addition of H2 to an
alkene.
▪ A metal catalyst speeds up
the rate of the reaction.
▪ The product of
hydrogenation is an alkane.

Addition
b. Halogenation
▪ The addition of halogen (X2)
to an alkene.
▪ X2 is usually Cl2 or Br2.
▪ The product of halogenation POLYMERIZATION
is a dihalide.
- Are large molecules made up of repeating units of
smaller molecules covalently bonded together.
- In polymerization, the monomer C=C double bonds are
broken and single bonds linking the monomers
c. Hydrohalogenation together are formed.
▪ The addition of HX (HCl or
HBr) to an alkene.
▪ The product is an alkyl
halide.

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 AROMATICS (arenes)

ALKYNES (acetylene) - Aromatics are compounds that contain a benzene ring.

- It have a characteristic gasoline-like odor.
- Alkynes are compounds that contain a carbon-carbon ▪ Benzene – simplest aromatic hydrocarbon. It
triple bond. CnH2n-2 has a hybrid structure. All three electron pairs
▪ Acyclic alkynes – contain chains of C atoms in the double bonds are delocalized in the six-
with triple bonds but no rings. CnH2n-2 membered ring.
▪ Cycloalkynes – contain chains of C atoms
joined in one or more rings with triple bonds.

Physical Properties:
➢ Alkynes have a slightly higer boiling point and melting
point than alkanes and alkenes.
▪ Hybridization and geometry
Physical Properties:
➢ Non-polar
➢ Immiscible in water
➢ Soluble in alcohol and ether
➢ Low melting and boiling point
▪ Aromatic > Alkyne > Alkane > Alkene
➢ Often unreactive due to three alternating double bonds.
➢ Useful as solvents for other nonpolar compounds.
➢ Aromatic hydrocarbons ar especially stable due to
resonance stability.
▪ Three alternating double bonds.

➢ Alkynes are insoluble in water. Chemical Properties:

➢ Benzene do not undergo addition reaction.
Chemical Properties: ➢ Aromatics undergo electrophilic aromatic substitution.
➢ Alkynes undergo the same reaction as alkenes. ➢ Arenes undergo the same reactions as alkanes.

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 Delocalization is temporarily broken as Cigarette lighters and
X replaces H on the ring, which uses Butane
Electrophilic portable stoves
energy.
Aromatic
• Energy is recovered when C5H12 – C12H26
Substition
delocalization is re- Octane Rating (the
established. Gasoline
measurement of the quality
Petroleum or performance of gasoline)

Kerosene C12H23 – C16H34

Diesel C15H23 – C18H38
Napthalene Mothballs
Used in the production of
Aromatic Anthracene red dye alizarin (wood
Hydrocarbo preservative)
ns Compound found in coal
Benzo(a)pyre
tar, tobacco and grilled
ne
meats (carcinogenic)
- Anesthetic
- Non-irritating to
mucous
membranes
Cyclopropane - Does not depress
respiration
- No longer used
- Extremely
flammable
- Colorless,
flammable gas
- Sweet taste and
odor
- Naturally occurring
hormone in plants
Ethylene ▪ Inhibits
growth
▪ Promotes
leaf fall
▪ Promotes
ripening
HETEROCYCLIC HYDROCARBONS of fruits
- A class of cyclic compounds containing an atom or - Non-pro-vitamin A
atoms other than carbon in its ring. carotenoid
▪ Nitrogen, oxygen, sulfur, phosphorus, etc. - Red (and pink)
pigment
- Antioxidant
▪ Can help
prevent
cellular
damage
Lycopene
by ROS
that could
lead to
chronic
EXAMPLES OF HYDROCARBONS illness or
Methane Largest component cancer.
- Its bioavailability
Transportation Fuel increases upon
Natural Gas Ethane
Refrigerant cooking.
Propane Used for cooking

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 - Used as a solvent LESSON #2: PHENOLS
in the printing,
rubber and leather
PHENOLS
industries.
- Cleaning agent
▪ Used in
cleaning
microsco
pes
- Thinner for paint
Xylene - Varnishes
- Used in tissure
processing, - Phenols and cresols are obtain from coal tar.
staining and cover - Phenols are organic compounds in which a hydroxyl
slipping in the group is bonded to an aromatic ring.
histology - They are also known as carbolic acid.
laboratory
Physical Properties:
➢ Have higher boiling points
▪ Due to resonance stability of the benzene
ring.
➢ Solubility
TEST FOR HYDROCARBONS ▪ Partially soluble in water
▪ Most other phenols are insoluble in water.
IGNITION TEST ▪ Soluble in 5% NaOH
▪ Acid + Base = Salt
- Hydrocarbons exhibit luminous flame with soot due to ➢ Acidity: Weak Acid
incomplete combustion. ▪ The corresponding phenoxide (phenolate)
- Increase in C-H bonds = high luminosity (orange flame) anions are stabilized by resonance.
➢ Esterification – phenols react slowly with carboxylic
a. Aliphatic Saturated Hydrocarbons – luminous acids to form esters.
flame no soot to less sooty. ▪ Phenols react faster using acyl chloride (acid
chlorides) at room temp or acid anhydrides at
b. Aliphatic unsaturated and Aromatic Hydrocarbons warm temp.
– luminous flame with high amount of soot.

BAEYER’S TEST

- Test for unsaturated hydrocarbon.

- Positive result: brown precipitate (MnO4)
- Undergoes oxidation reaction where the alkaline
KmnO4 is precipitated out.

ELECTROPHILIC AROMATIC SUBSTITUTION

- Reaction in which the hydrogen atom of an aromatic

ring is replaced as a result of an electrophilic attack on
the aromatic ring.
- Positive result: White precipitate or Cloudy solution.
EXAMPLE OF PHENOLS
- 2-isopropyl-5-methylphenol
Thymol - Thyme
- Antiseptic, antibacterial
Catechol - Poison Ivy
- 8-methyl-N-vanillyl-6-nonenamide
Capsaicin - Chili peppers
- analgesic

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 - 4-hydroxy-3-methoxybenzaldehyde
Vanillin - Vanilla bean
- Flavoring
- 2-isopropyl-5-methylphenol
Eugenol - Cloves
- Antiseptic and anti-inflammatory
- Nutmeg
Isoeugenol
- Flavoring: Fragrance
ANTISEPTIC VS DISINFECTANT
- Kills microorganism on living tissue.
- Liquid phenol/carbolic acid
Antiseptic
- Active ingredients of some hand
cleaners
- Kills microorganism on inanimate
objects.
Disinfectant - 2-benzyl-4-chlorophenol and O-
polyphenol
- Active ingredient of lysol
TEST FOR PHENOLS
LITMUS TEST
- Phenol is a weak acid, it gives red colour with litmus
paper.
- A test to identify if the substance is acidic or basic.
▪ Positive Result: Blue to Red – Acid
FERRIC CHLORIDE TEST
- Test for phenols as they form intensely colored
complexes with Fe3+.
Positive Results:
▪ Phenol – violet colored solution
▪ Alpha naphtol – light brown solution
▪ Catechol – dark green color
▪ Thymol – yellow solution
▪ Pyrogallol – blue to red color
BROMINE WATER TEST
- Phenols undergo electrophilic substitution reaction
with bromine.
▪ The orange-red color of the bromine solution
is decolorized forming 2,4,6-tribromophenol.
▪ Undergoes electrophilic aromatic
substitution.
▪ Positive result: White Precipitate
MILLON’S TEST
- Test for phenols or phenol-containing compound.
▪ Phenol group is first nitrated by nitric acid
and forms a complex with mercury ions
which produces a brick-red solution or
precipitate.
▪ Positive result: Reddish Brown (brick-red)
solution or precipitate
PHTHALEIN DYE TEST
- Phenol on heating with phthaleic anhydride in the
presence of sulphuric acid produces phenolphthalein,
which is colourless. Phenolphthalein gives pink colour
on treating with alkali.
▪ Used as acid-base indicator.
▪ Positive result: Colorless in Acid/Pink in Base
MODULE 5
INTRODUCTION
Alcohols are compounds containing the hydroxyl (-OH)
functional group bonded to an alkyl, R, as they may be
represented by the general formula ROH. (109)
Physical Properties:
➢ Bent molecular shape
▪ Due to oxygen atom, has a bond angle of
109.5.
➢ Have a net dipole
▪ Has two polar bonds, C-O and O-H.
➢ Contains both polar and nonpolar character.
➢ Capable of intermolecular hydrogen bonding.
▪ Thus, stronger IMF than hydrocarbons with
the same number of carbons.
▪ Higher boiling point.
▪ The oxygen can bond with the hydrogen
atom.
➢ Soluble in organic solvents
▪ Alcohols with 5 or less carbons are soluble in
water.
▪ Alcohols with more than 5 carbons are
insoluble in water – more van der waals
forces.
▪ Increase in number of -OH – increase
solubility in water.
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