STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
STATION 1:
NOMENCLATURE & PHYSICAL PROPERTIES
JOM SKOR KIMIA SK025 SESI 2019/2020
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
NOMENCLATURE
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
PHYSICAL PROPERTIES
BOILIN BASICITY
SOLUBILITY ACIDITY
G
POINT
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
BOILIN
G
POINT
Depends on the strength of intermolecular forces
between molecules.
C-H bond is a non-polar bond. Intermolecular forces
between molecules are Van der Waals forces.
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
BOILIN
Boiling Point of Alkane
G
POINT
Factors Effect of Boiling Point
1. Molecular weight / Molar mass
As molecular weight increases; molecular size bigger,
larger the surface area in contact between molecules,
stronger Van der Waals forces,
higher heat energy required to overcome the Van der Waals
forces.
higher boiling points.
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
Boiling Point of Alkane
BOILIN
G Factors Effect of Boiling Point
POINT
2. Isomeric Alkanes
a) Effect of branching
As molecules with more branches, become more compact,
smaller surface area in contact between molecules,
weaker Van der Waals forces,
lower heat energy required to overcome the Van der Waals forces.
lower boiling point.
REMEMBER!!
Compare effect of branching chain among the isomers only (same molecular weight)
Boiling point of branched alkane is higher than straight alkane if number of C is greater
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
Boiling Point of Alkane
BOILIN
G Factors Effect of Boiling Point
POINT
2. Isomeric Alkanes
Cyclic Compound
the shape is more compact and flat,
intermolecular forces increase due to the larger surface area in
contact between molecules.
stronger Van der Waals forces,
higher heat energy required to overcome the Van der Waals forces.
higher boiling point compare to alkanes.
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
Boiling Point of Alkane
BOILIN
G
POINT
For same molecular weight,
cyclic compound > straight chain > branching chain
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
BOILIN
Boiling Point of Alcohol
G • The high electronegativity difference between
POINT
O and H makes alcohol molecules highly polar.
• Alcohol molecules are attracted to each other by
hydrogen bond
H H H H
O O O O
R R R R
• Higher energy is needed to separate the molecules.
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
BOILIN
Boiling Point of Alcohol
G
POINT
Factors Effect of Boiling Point
1. Molecular weight / Molar mass
Molecular weight increases, total surface area increase, BP
increases due to the increase in strength of Van der Waals
Forces.
BP of R-OH is higher than the corresponding hydrocarbon
due to the ability of alcohol to form hydrogen bond.
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
BOILIN
Boiling Point of Alcohol
G
POINT
Factors Effect of Boiling Point
2. Number of OH group
Number of –OH group increases, BP increases due to the
increase in the number of hydrogen bond
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
BOILIN
Boiling Point of Alcohol
G
POINT
Factors Effect of Boiling Point
3. Number of branched (isomeric alcohol)
Straight chain has a bigger contact area compared to branched
alcohol, hence, stronger Van der Waals forces, higher BP.
BP straight chain alcohol >branched chain alcohol
1° > 2° > 3°
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
Boiling Point of Carboxylic Acid
BOILIN
Carboxylic acid relatively high boiling point.
G
POINT - due to the ability of the RCOOH to form intermolecular
hydrogen bonds.
The high boiling of carboxylic acid result from formation of a stable
hydrogen-bonded dimer.
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
Boiling Point of Carboxylic Acid
BOILIN
G High energy is needed to separate the molecules because
POINT of the strong hydrogen bond between molecules in a
dimer.
The boiling points of carboxylic acid acids are higher than
those of alcohols, ketones, aldehydes and alkanes with
similar molecular mass.
Dicarboxylic acids have higher boiling points due to the
formation of more hydrogen bonds with each other.
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
Boiling Point of Amine
BOILIN 3o amine
G
3o amine is a polar molecule. Between 3o amine molecules
POINT
there are only Van der Waals forces (London forces and
dipole-dipole forces). No hydrogen bond can be formed
between molecules (no H atom directly attached to N
atom). Hence, 3o amine has the lowest boiling point.
2o amine
2o amine is a polar molecule. Between 2o amine molecules
there are Van der Waals forces (London forces and dipole-
dipole forces) and hydrogen bonds. But, the N atom is in
the middle of the chain, making the permanent dipoles
(dipole-dipole forces) to be weaker. Hence, 2o amine
has higher boiling point than 3o amine but lower
boiling point than 1o amine.
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
Boiling Point of Amine
BOILIN 1o amine
G
POINT
1o amine is polar molecule. Between 1o amine
molecules there are Van der Waals forces (London
forces, dipole-dipole forces (more effective than
2o amine) and hydrogen bonds. Hence, 1o amine
has highest boiling point.
Order of increasing boiling point:
3o amines < 2o amines < 1o amines
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
BOILIN Amine with alkane, haloalkane, alcohol, carbonyl
G
POINT
compound and carboxylic acid
Alkane < haloalkane < 3o amine < carbonyl compound ≈ 1o and 2o amines < alcohol < carboxylic acid
- Amine can form hydrogen bonds between molecules. Hence, amine has higher boiling point than
alkane and haloalkane of similar molecular weight.
- 3o amine cannot form hydrogen bonds between molecules. Hence, 3o has lower boiling point.
- 1o and 2o amines have boiling point close to carbonyl compounds (ketones and aldehydes).
- 1o and 2o amines have lower boiling point than alcohol because N is less electronegative than O.
Hence, hydrogen bonds between 1o and 2o amine molecules are weaker compared to alcohol.
- Carboxylic acid has the highest boiling point because the molecules can form dimers, closely
packed to give stronger hydrogen bonds between molecules.
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
SOLUBILITY
Ability to intermolecular forces with its
solvent (water or organic solvent)
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
Solubility in Water Solubility in Organic Solvent
(Polar Solvent) (Non-Polar Solvent)
SOLUBILITY Requirement: Requirement:
• Able to form hydrogen bond with • Non polar molecules dissolves in non-polar
water molecules. (F, O, N attach to H) solvent
• Polar molecules can dissolve in polar
solvent.
Alkanes & cycloalkanes are insoluble in Alkanes soluble in non-polar solvent.
water
Reason: Reason:
• Unable to form hydrogen bond with • Can form intermolecular forces with non-
water molecule. polar solvent (benzene, chloroform, carbon
• Non-polar molecules. tetrachloride and other hydrocarbon)
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
SOLUBILITY OF ALCOHOL IN WATER
SOLUBILITY
- Lower alcohols (≤ 5C) − completely soluble in water.
- Longer C chain (>5C) – insoluble in water.
- Alcohols and water presence –OH group in the molecules.
- Therefore, they have the ability to form intermolecular hydrogen
bonding.
- −OH group gives alcohol a hydrophilic character.
R OH
Hydrophobic part Hydrophilic part
(Weak interaction with water molecule) (Form strong hydrogen bond with water molecule)
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
H H H H
O O O O
SOLUBILITY H R H R
Factors affecting solubility:
Molecular weight Number of –OH group
As the molecular weight increases, the When number of –OH groups increases,
hydrophobic area (R group) becomes the solubility in water also increases.
larger. due to ability to form more
water solubility decreases. hydrogen bonds with water
molecule increases.
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
SOLUBILITY OF CARBOXYLIC ACID IN WATER
SOLUBILITY Carboxylic acids (C1−C5) completely soluble in water due to
the formation of hydrogen bonds with water molecule.
Increase in molecular mass increases
The size of alkyl group
The hydrophobic area decreases the
solubility in water.
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
Aliphatic carboxylic acids with C >
5 are insoluble in water COOH
SOLUBILITY
Aromatic carboxylic acids are
COOH
slightly soluble in water
due to the huge aromatic ring
(bigger hydrophobic area)
Dicarboxylic acids are relatively
more soluble in water COOH
due to the formation of more
COOH
hydrogen bonds with water
molecules
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
ACIDITY
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STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
Basicity of Ammonia, Aliphatic Amines and Aromatic Amines
BASICITY
SOLUBILITY
Order of increasing basicity:
aromatic amine < ammonia < aliphatic amine
< <
Basicity of ammonia derivative weak bases depends on the ease of
the lone pair on N atom to accept H+. Easier for the lone pair on N
to accept H+, more basic is the weak base.
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
Basicity of Ammonia, Aliphatic Amines and Aromatic Amines
BASICITY
SOLUBILITY
Aromatic amine (aniline) is the weakest base. Electron withdrawing group (phenyl
ring) and resonance effect (delocalisation of the lone pair on N into the -system of the
benzene ring) decreases the electron density on N and makes the lone pair on N harder
to accept H+ ion.
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
Basicity of Ammonia, Aliphatic Amines and Aromatic Amines
BASICITY
SOLUBILITY
Ammonia is stronger base than aromatic amine. No electron withdrawing group
and resonance effect to reduce the electron density on N and make the lone pair
on N hard to accept H+ ion.
OR
Ammonia is weaker base than aliphatic amine. No electron donating group to
increase the electron density on N and make the lone pair on N easier to accept H+
ion.
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
Basicity of Ammonia, Aliphatic Amines and Aromatic Amines
BASICITY
SOLUBILITY
Aliphatic amine (cyclohexanamine) is strongest base. Electron donating
group (alkyl group) increases the electron density on N and makes the
lone pair on N easier to accept H+ ion.
STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
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STATION 1: NOMENCLATURE & PHYSICAL PROPERTIES
