Module 1 - Introduction To Organic Chemistry

1 Introduction to
Organic Chemistry
1.1 What is Organic Chemistry?
1.2 The Unique Nature of Carbon
1.3 Classification of Organic Compounds
1.4 Factors Affecting the Physical Properties of
Organic Compounds
1
1 New Way Chemistry for Hong Kong A-Level Book 3A
1.1
What is Organic
Chemistry?
2
1.1 What is Organic Chemistry (SB p.2)
Organic Chemistry
• Chemistry of the compounds present

in living organisms.
• They all contain carbon.
• Organic Chemistry is the Chemistry
of Carbon.
3
Natural Sources of Organic Compounds
Living Carbohydrates /
things Proteins / Fats /
Vitamins / Antibiotics
A variety of
organic products
obtained from
living things
4
Natural Sources of Organic Compounds

Fractional distillation / Alkanes /
Alkenes /
Crude oil destructive distillation
Alkynes /
or coal
Aromatic
hydrocarbons
Check Point 21-1

A variety of
useful products
derived from
crude oil and coal
5
Development of Organic Chemistry as a

Science
In the past …,
Chemistry
Organic Inorganic
compounds compounds
obtained from obtained from
living organisms non-living sources
6
Development of Organic Chemistry as a Science

In 1828, Wohler (a German chemist)
(Inorganic (Organic
compound) compound)
7
Development of Organic Chemistry as a Science

Redefining … ...
Organic chemistry is the study of carbon

compounds (except CO, CO2, carbonates,
hydrogencarbonates, carbides and cyanides)
obtained from natural sources or
synthesized in the laboratories.
8
1.2
The Unique
Nature of Carbon
9
1.2 The Unique Nature of Carbon (SB p.5)
Ability to form four strong covalent bonds
• Electronic configuration of carbon

(ground state) : 1s22s22p2
Carbon (ground state)
10
Ability to form four strong covalent bonds
• Each carbon atom has four unpaired

electrons when excited
• Tend to form four strong covalent bonds
Carbon (excited state)

11
Ability to Catenate
• Carbon atoms link together to form chains of

varying length, branched chains and rings of
different sizes
• Catenation:
è Ability of atoms in forming stable bonds
with itself, hence joining up into chains or
rings
12
Ability to Catenate
C – C > Si – Si > Ge – Ge > Sn – Sn
Bond strength ¯ as bond length
13
Ability to Catenate
C–C>N–N>O–O
Bond strength ¯ as the number of lone pairs
14
Ability to Catenate
CnH2n+2 n = 1,2,3,…(no limit for n)

SinH2n+2 n = 1 to 6 only ® silanes
GenH2n+2 n = 1 to 3 only ® germanes
SnnH2n+2 Only SnH4 (stannane) exists
15
Ability to Form Multiple Bonds

sp3
4s bonds
sp2
1p bond, 3s bonds
sp
2p bonds, 2s bonds
Carbon (excited state)

16
Single bond Double bond Triple bond
* X = halogens
17
1.3
Classification of
Organic
Compounds
18
1.3 Classification of Organic Compounds (SB p.7)
Functional Groups
• Organic compounds are classified by

the the presence of characteristic
functional groups.
19
Functional Groups
A functional group is defined as an

atom or a group of atoms that
effectively determines the chemical
properties of an organic compound.
20
Functional Groups
21
Functional Groups
• Propane does not react with sodium
• Ethanol and propan-1-ol react with

sodium to give hydrogen gas
22
Functional Groups
and
• have similar chemical properties

è they contain the same functional group –OH
è they are classified into the same
23
homologous series — alcohols
Homologous Series
A homologous series is a series of
compounds that have the same functional
group, and each member differs from
the next member by a – CH2 – unit in
their formulae.
CH4 C2H6 C3H8 C4H10
CH2 CH2 CH2

24
Number IUPAC Molecular Condensed Structural
of carbon name formula structural formula
atom(s) formula
1 Methane CH4 CH4
2 Ethane C2H6 CH3CH3
3 Propane C3H8 CH3CH2CH3
4 Butane C4H10 CH3CH2CH2CH3
25 New Way Chemistry for Hong Kong A-Level 3A

The first four members of straight-chain alkanes
Number IUPAC Molecular Condensed Structural
of carbon name formula structural formula
atom(s) formula
1 Methanol CH3OH CH3OH
2 Ethanol C2H5OH CH3CH2OH
3 Propan-1- C3H7OH CH3CH2CH2OH

ol
4 Butan-1- C4H9OH CH3CH2CH2CH2OH

ol
26 New Way Chemistry for Hong Kong A-Level 3A
The first four members of straight-chain alcohols
Homologous Series
• Members in the same series can be
represented by a general formula.
e.g. alkanes: CnH2n+2
alkenes: CnH2n
alkynes: CnH2n-2
27
Homologous Series
• Members in the same series can be
represented by a general formula.
e.g. alcohols: CnH2n+1OH
aldehydes: CnH2n+1CHO
carboxylic acids: CnH2n+1COOH
28
Homologous Series
Functional group
Chemical
of an organic
properties
compound
Members of a homologous series

have similar chemical properties
29
Homologous Series
• The physical properties change gradually
along the homologous series
• e.g. the longer the carbon chain in the

molecule ( or the greater the
molecular mass)
è the greater the attractive force
between molecules
è the higher the melting point,
boiling point and density
30
Some physical properties of the first 20 members of
straight-chain alkanes
State (at
Number Density of
room
of Molecula Melting Boiling solid / liquid
temperature
carbon r formula point (°C) point (°C) at 20°C (g cm–
and
atom(s) 3)
pressure)
1 CH4 Gas –183 –161 –
2 C2 H6 Gas –172 –89 –
3 C3 H8 Gas –188 –42 –
4 C4H10 Gas –135 0 –
5 C5H12 Liquid –130 36 0.626
6 C6H14 Liquid –95 69 0.657
7 C7H16 Liquid –91 98 0.684
8 C8H18 Liquid –57 126 0.703
9 C9H20 Liquid –54 151 0.718
31
31 10 C10H22 Liquidfor Hong Kong–30
New Way Chemistry A-Level Book 3A174 0.730
Some physical properties of the first 20 members of
straight-chain alkanes
State (at
Number Density of
room
of Molecula Melting Boiling solid / liquid
temperature
carbon r formula point (°C) point (°C) at 20°C (g cm–
and
atom(s) 3)
pressure)
11 C11H24 Liquid –26 196 0.740
12 C12H26 Liquid –10 216 0.749
13 C13H28 Liquid –7 233 0.753
14 C14H30 Liquid –3 260 0.761
15 C15H32 Liquid 10 271 0.769
16 C16H34 Liquid 18 287 0.773
17 C17H36 Liquid 22 302 0.778
18 C18H38 Solid 28 316 0.777
19 C19H40 Solid 32 330 0.777
32
32 20 C20H42 Solid for Hong Kong37
New Way Chemistry A-Level Book 344
3A 0.785
1.4
Factors Affecting the
Physical Properties of
Organic Compounds
33
1.4 Factors Affecting the Physical Properties of Organic Compounds
Main Factors Affecting the Physical

Properties of Organic Compounds
1. Structure of the functional group

1.1 Dipole moment of the molecule
1.2 Formation of hydrogen bonding
2. Length of carbon chains (London dispersion forces)
34
Structure of Functional Group
• Molecules having a polar functional

group have a higher b.p. than others
with a non-polar functional group of
similar molecular masses
! Stronger intermolecular attraction
among molecules
35
Structure of Functional Group

Molecule Relative Boiling point
molecular (oC)
mass
Molecules CH3CH2CH2OH 60 97.2
with polar
CH3CH2CH2NH2 59 48.6
functional
groups CH3CH2Cl 64.5 12.5
CH3CH2COOH 60 141
Molecules CH3CH2CH2CH3 58 -0.5
with non-
CH3CH2CH=CH2 56 -6.2
polar
functional CH3CH2CºCH 54 8.1
36
groups
Dipole Moment of Molecule

• Tetrachloromethane has 4 polar bonds in the
molecule
• M.p. and b.p. are very low
! the molecule is non-polar
è the molecule is tetrahedrally
symmetrical
è the dipole moments of the
C ¾ Cl bond cancel each other
37
Examples of Polar Molecules with

Net Dipole Moment
38
Examples of Non-polar Molecules

with No Net Dipole Moment
39
Solubility of Organic Molecules

• Depends on the polarity of organic
molecules and the solvent
• Non-polar or weakly polar compounds
dissolve readily in non-polar or weakly
polar solvents
• Highly polar compounds dissolve readily
in highly polar solvents
• “Like dissolves like”
40
Solubility of Organic Molecules
Hexane in Hexane in water

tetrachloromethane
41
Why does Hexane Dissolve Readily in

Tetrachloromethane?
Intermolecular forces among hexane Intermolecular forces

molecules and those among » between hexane and
tetrachloromethane molecules tetrachloromethane
molecules
42
Why is Hexane Insoluble in Water?
43
Formation of Hydrogen Bonding

• Molecules having ¾OH or ¾ NH2 groups
are able to form hydrogen bonds
• Hydrogen bonds affect the physical
properties of alcohols and amines with
low molecular masses
44
Why does Propan-1-ol have a Higher Boiling Point?
45
Formation of Hydrogen Bonding

• Also affect the solubility of a molecule
• Molecules with ¾OH groups are able
to form hydrogen bonds with
surrounding water molecules
è Soluble in water
46
Length of Carbon Chains
• Molecules with higher molecular masses

have higher m.p., b.p. and density
! Higher molecular masses
è Large molecular sizes
è Stronger London dispersion
forces among molecules
47
• Molecules with branched chains

è b.p. and density lower than its
straight-chain isomer
! Straight-chain isomers have greater
surface area in contact with each other
è Greater attractive force among the
molecules
48

• Molecules with branched chains
è m.p. higher than its straight-chain
isomer
! Branched-chain isomers are more
spherical
è Packed more efficiently in solid state
è Extra energy is needed to break
down the efficient packing
49
General Functional Example
Family
formula group Formula IUPAC name
Alkane RH (Nil) CH3CH3 Ethane
RCH = CH2
RCH = CHR
Alkene Carbon- CH2 = CH2 Ethene
R2C = CHR
carbon
R2C = CR2 double bond
–CºC–
RC º CH Carbon-
Alkyne HC º CH Ethyne
RC º CR carbon triple
bond
Aromatic
ArH Benzene
hydrocarbon
Phenyl group
50 R = CnH2n+1 –
Family
¾X
Haloalkane RX CH3Cl Chloromethane
halo group
¾ OH
Alcohol ROH CH3OH Methanol
hydroxyl group
¾O¾ CH3 ¾ O ¾
Ether R¾O ¾ R Methoxymethane
oxy group CH3
Aldehyde Methanal
carbonyl group
R = CnH2n+1 –
51
Family
Ketone Propanone
carbonyl group
Carboxylic
Ethanoic acid
acid
carboxyl group
RNH2
Amine R2NH CH3NH2 Methylamine
R3 N amino group
¾CºN
Nitrile RCºN CH3CN Ethanenitrile
nitrile group
52
52 R = CnH2n+1 –New Way Chemistry for Hong Kong A-Level Book 3A
Family
Methyl
Ester
ethanoate
ester group
Ethanoyl
Acyl halide
chloride
acyl halide
group
Amide Ethanamide
53
amide group
New Way Chemistry for Hong Kong A-Level 3A
53 New Way Chemistry for Hong Kong A-Level Book 3A R = CnH2n+1 –

Family
Acid Ethanoic
anhydride anhydride
acid anhydride
group
R = CnH2n+1 –
54
The END
55

Module 1 - Introduction To Organic Chemistry

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Module 1 - Introduction To Organic Chemistry

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1 Introduction to

• Chemistry of the compounds present

Natural Sources of Organic Compounds

Natural Sources of Organic Compounds

Check Point 21-1

Development of Organic Chemistry as a

Development of Organic Chemistry as a Science

Development of Organic Chemistry as a Science

Organic chemistry is the study of carbon

Ability to form four strong covalent bonds

• Electronic configuration of carbon

Carbon (ground state)

Ability to form four strong covalent bonds

• Each carbon atom has four unpaired

• Tend to form four strong covalent bonds

Carbon (excited state)

• Carbon atoms link together to form chains of

Bond strength ¯ as bond length ­

Bond strength ¯ as the number of lone pairs ­

CnH2n+2 n = 1,2,3,…(no limit for n)

Ability to Form Multiple Bonds

Carbon (excited state)

• Organic compounds are classified by

A functional group is defined as an

• Propane does not react with sodium

• Ethanol and propan-1-ol react with

• have similar chemical properties

CH4 C2H6 C3H8 C4H10

CH2 CH2 CH2

2 Ethane C2H6 CH3CH3

3 Propane C3H8 CH3CH2CH3

4 Butane C4H10 CH3CH2CH2CH3

25 New Way Chemistry for Hong Kong A-Level 3A

2 Ethanol C2H5OH CH3CH2OH

3 Propan-1- C3H7OH CH3CH2CH2OH

4 Butan-1- C4H9OH CH3CH2CH2CH2OH

e.g. alkanes: CnH2n+2

e.g. alcohols: CnH2n+1OH

carboxylic acids: CnH2n+1COOH

Members of a homologous series

• e.g. the longer the carbon chain in the

Main Factors Affecting the Physical

1. Structure of the functional group

Structure of Functional Group

• Molecules having a polar functional

Structure of Functional Group

Dipole Moment of Molecule

Examples of Polar Molecules with

Examples of Non-polar Molecules

Solubility of Organic Molecules

Solubility of Organic Molecules

Hexane in Hexane in water

Why does Hexane Dissolve Readily in

Intermolecular forces among hexane Intermolecular forces

Why is Hexane Insoluble in Water?

Formation of Hydrogen Bonding

Why does Propan-1-ol have a Higher Boiling Point?

Formation of Hydrogen Bonding

Length of Carbon Chains

• Molecules with higher molecular masses

Length of Carbon Chains

• Molecules with branched chains

Length of Carbon Chains

Bond strength ¯ as bond length

Bond strength ¯ as the number of lone pairs