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
hydrophobic area (R group) becomes
larger.
 water solubility decreases.
 
 When number of –OH groups increases,
the solubility in water also increases.
 due to ability to form more
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

https://youtu.be/8Shx0TagLZI
 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