Anda di halaman 1dari 59

21

21.1
21.2
21.3
21.4

1
1

Introduction to
Organic Chemistry
What is Organic Chemistry?
The Unique Nature of Carbon
Classification of Organic Compounds
Factors Affecting the Physical Properties of
Organic Compounds

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

21.
1
What is
Organic
Chemistry?
2
2

New Way Chemistry for Hong Kong A-Level 3A


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

21.1 What is Organic Chemistry (SB p.2)

Organic Chemistry

3
3

Chemistry of the compounds present


in living organisms.

They all contain carbon.

Organic Chemistry is the Chemistry


of Carbon.

New Way Chemistry for Hong Kong A-Level 3A


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

21.1 What is Organic Chemistry (SB p.4)

Natural Sources of Organic Compounds


Living
things

Carbohydrates /
Proteins / Fats /
Vitamins /
Antibiotics

A variety of
organic products
obtained from
living things
4
4

New Way Chemistry for Hong Kong A-Level 3A


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

21.1 What is Organic Chemistry (SB p.4)

Natural Sources of Organic Compounds


Crude oil
or coal

Fractional distillation /
destructive distillation

Alkanes /
Alkenes /
Alkynes /
Aromatic
hydrocarbons
Check Point 21-1

5
5

A variety of
useful products
derived from
crude oil and coal
New Way Chemistry for Hong Kong A-Level 3A
New Way Chemistry for Hong Kong A-Level Book 3A

21.1 What is Organic Chemistry (SB p.3)

Development of Organic Chemistry


as a Science
In the past
,

Chemistry
Chemistry

Organic
Organic
compounds
compounds
obtained from
living organisms
6
6

Inorganic
Inorganic
compounds
compounds
obtained from
non-living sources

New Way Chemistry for Hong Kong A-Level 3A


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

21.1 What is Organic Chemistry (SB p.3)

Development of Organic Chemistry


as a Science
In 1828, Wohler (a German chemist)

(Inorganic
compound)
7
7

(Organic
compound)

New Way Chemistry for Hong Kong A-Level 3A


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

21.1 What is Organic Chemistry (SB p.3)

Development of Organic Chemistry


as a Science
Redefining ...
Organic chemistry
chemistry is
is the
the study
study of
of carbon
carbon
Organic
compounds (except
(except CO,
CO, CO
CO22,, carbonates,
carbonates,
compounds
hydrogencarbonates, carbides
carbides and
and
hydrogencarbonates,
cyanides) obtained
obtained from
from natural
natural sources
sources or
or
cyanides)
synthesized in
in the
the laboratories.
laboratories.
synthesized

8
8

New Way Chemistry for Hong Kong A-Level 3A


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

21.
2 The Unique
Nature of
Carbon
9
9

New Way Chemistry for Hong Kong A-Level 3A


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

21.2 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
10

New Way Chemistry for Hong Kong A-Level 3A


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

21.2 The Unique Nature of Carbon (SB p.5)

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
11

New Way Chemistry for Hong Kong A-Level 3A


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

21.2 The Unique Nature of Carbon (SB p.5)

Ability to Catenate
Carbon atoms link together to form
chains of varying length, branched
chains and rings of different sizes
Catenation:
Ability of atoms in forming stable
bonds with itself, hence joining up
into chains or rings
12
12

New Way Chemistry for Hong Kong A-Level 3A


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

21.2 The Unique Nature of Carbon (SB p.5)

Ability to Catenate
C C > Si Si > Ge Ge > Sn Sn
Bond strength as bond length

13
13

New Way Chemistry for Hong Kong A-Level 3A


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

21.2 The Unique Nature of Carbon (SB p.5)

Ability to Catenate
CC>NN>OO
Bond strength
as the number of lone pairs

14
14

New Way Chemistry for Hong Kong A-Level 3A


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

21.2 The Unique Nature of Carbon (SB p.5)

Ability to Catenate

15
15

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

New Way Chemistry for Hong Kong A-Level 3A


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

21.2 The Unique Nature of Carbon (SB p.5)

Ability to Form Multiple Bonds


sp3
sp2
sp

4 bonds
1 bond, 3 bonds
2 bonds, 2 bonds

Carbon (excited state)


16
16

New Way Chemistry for Hong Kong A-Level 3A


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

21.2 The Unique Nature of Carbon (SB p.6)


Single bond

Double bond

Triple bond

* X = halogens

17
17

New Way Chemistry for Hong Kong A-Level 3A


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

21.2 The Unique Nature of Carbon (SB p.6)

Example 21-2

18
18

Check Point 21-2

New Way Chemistry for Hong Kong A-Level 3A


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

21.
3Classification
of Organic
Compounds
19
19

New Way Chemistry for Hong Kong A-Level 3A


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

21.3 Classification of Organic Compounds (SB p.7)

Functional Groups

20
20

Organic compounds are classified by


the the presence of characteristic
functional groups.

New Way Chemistry for Hong Kong A-Level 3A


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

21.3 Classification of Organic Compounds (SB p.7)

Functional Groups
A functional
functional group
group is
is defined
defined as
as an
an
A
atom or
or aa group
group of
of atoms
atoms that
that
atom
effectively determines
determines the
the chemical
chemical
effectively
properties of
of an
an organic
organic compound.
compound.
properties

21
21

New Way Chemistry for Hong Kong A-Level 3A


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

21.3 Classification of Organic Compounds (SB p.7)

Functional Groups

22
22

New Way Chemistry for Hong Kong A-Level 3A


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

21.3 Classification of Organic Compounds (SB p.7)

Functional Groups

23
23

Propane does not react with sodium

Ethanol and propan-1-ol react with


sodium to give hydrogen gas

New Way Chemistry for Hong Kong A-Level 3A


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

21.3 Classification of Organic Compounds (SB p.7)

Functional Groups

and

have similar chemical properties


they contain the same functional group OH
they are classified into the same
homologous series alcohols
24
24

New Way Chemistry for Hong Kong A-Level 3A


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

21.3 Classification of Organic Compounds (SB p.12)

Homologous Series
A homologous
homologous series
series is
is aa series
series of
of
A
compounds that
that have
have the
the same
same functional
functional
compounds
group, and
and each
each member
member differs
differs from
from
group,
the next
next member
member by
by aa CH
CH22 unit
unit in
in
the
their formulae.
formulae.
their
CH4

C2H6
CH2

25
25

C3H8
CH2

C4H10
CH2

New Way Chemistry for Hong Kong A-Level 3A


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

21.3 Classification of Organic Compounds (SB p.12)

Number of
carbon
atom(s)

IUPAC
name

Molecular
formula

Condensed
structural
formula

Methane

CH4

CH4

Ethane

C2H6

CH3CH3

Propane

C3H8

CH3CH2CH3

Butane

C4H10

CH3CH2CH2CH3

26
26

New Way Chemistry for Hong Kong A-Level 3A


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

Structural
formula

The first four members of straight-chain alkanes

21.3 Classification of Organic Compounds (SB p.12)

Number of
carbon
atom(s)

IUPAC
name

Molecular
formula

Condensed
structural
formula

Methanol

CH3OH

CH3OH

Ethanol

C2H5OH

CH3CH2OH

Propan-1ol

C3H7OH

CH3CH2CH2OH

Butan-1ol

C4H9OH

CH3CH2CH2CH2OH

27
27

New Way Chemistry for Hong Kong A-Level 3A


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

Structural
formula

The first four members of straight-chain alcohols

21.3 Classification of Organic Compounds (SB p.13)

Homologous Series
Members in the same series can be
represented by a general formula.
e.g. alkanes: CnH2n+2
alkenes: CnH2n
alkynes: CnH2n-2
28
28

New Way Chemistry for Hong Kong A-Level 3A


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

21.3 Classification of Organic Compounds (SB p.13)

Homologous Series
Members in the same series can be
represented by a general formula.
e.g. alkanols: CnH2n+1OH
alkanals: CnH2n+1CHO
alkanoic acids: CnH2n+1COOH

29
29

New Way Chemistry for Hong Kong A-Level 3A


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

21.3 Classification of Organic Compounds (SB p.13)

Homologous Series
Functional group
of an organic
compound

Chemical
properties

Members of a homologous series


have similar chemical properties
30
30

New Way Chemistry for Hong Kong A-Level 3A


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

21.3 Classification of Organic Compounds (SB p.13)

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)
the greater the attractive force
between molecules
the higher the melting point,
boiling point and density
31
31

New Way Chemistry for Hong Kong A-Level 3A


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

21.3 Classification of Organic Compounds (SB p.13)

Some physical properties of the first 20 members of


straight-chain alkanes
State (at
Number
room
Density of
of
Molecular
Melting
Boiling
temperature
solid / liquid at
carbon formula
point (C) point (C)
and
20C (g cm3)
atom(s)
pressure)
1
2
3
4
5
6
7
8
9
32
32 10

CH4

Gas
183
C2H6
Gas
172
C3H8
Gas
188
C4H10
Gas
135
C5H12
Liquid
130
C6H14
Liquid
95
Liquid
91
C7H16
Liquid
57
C8H18
Liquid
54
C9H20
New Way Chemistry for Hong Kong A-Level 3A
Liquid for Hong Kong A-Level
30Book 3A
New Way Chemistry
C10H22

161
89
42
0
36
69
98
126
151
174

0.626
0.657
0.684
0.703
0.718
0.730

21.3 Classification of Organic Compounds (SB p.13)

Some physical properties of the first 20 members of


straight-chain alkanes
State (at
Number
room
Density of
of
Molecula
Melting
Boiling
temperature
solid / liquid at
carbon r formula
point (C) point (C)
and
20C (g cm3)
atom(s)
pressure)
11
12
13
14
15
16
17
18
19
33
33 20

C11H24

Liquid
26
Liquid
10
C13H28
Liquid
7
C14H30
Liquid
3
C15H32
Liquid
10
C16H34
Liquid
18
Liquid
22
C17H36
Solid
28
C18H38
Solid
32
C19H40
NewSolid
Way Chemistry for Hong Kong
3A
37A-Level
New Way Chemistry
for Hong Kong A-Level
Book 3A
C20H42
C12H26

196
216
233
260
271
287
302
316
330
344

0.740
0.749
0.753
0.761
0.769
0.773
0.778
0.777
0.777
0.785

21.3 Classification of Organic Compounds (SB p.13)

34
34

Example 21-3A

Example 21-3B

Example 21-3C

Check Point 21-3

New Way Chemistry for Hong Kong A-Level 3A


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

35
35

21.
4
Factors Affecting
the Physical
Properties of
Refer to notes on Bonding and Structure
Organic
pp.77-92 intermolecular forces
Compounds
New Way Chemistry for Hong Kong A-Level 3A
New Way Chemistry for Hong Kong A-Level Book 3A

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.17)

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)
36
36

New Way Chemistry for Hong Kong A-Level 3A


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

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.17)

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

37
37

New Way Chemistry for Hong Kong A-Level 3A


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

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.17)

Structure of Functional Group


Molecule

Molecules
with polar
functional
groups

38
38

Molecules
with nonpolar
functional
groups

Relative
molecular
mass

Boiling point
(oC)

CH3CH2CH2OH

60

97.2

CH3CH2CH2NH2

59

48.6

64.5

12.5

CH3CH2COOH

60

141

CH3CH2CH2CH3

58

-0.5

CH3CH2CH=CH2

56

-6.2

CH3CH2CCH

54

8.1

CH3CH2Cl

New Way Chemistry for Hong Kong A-Level 3A


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

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.18)

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


the molecule is tetrahedrally
symmetrical
the dipole moments of the
C Cl bond cancel each other

39
39

New Way Chemistry for Hong Kong A-Level 3A


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

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.18)

Examples of Polar Molecules


with Net Dipole Moment

40
40

New Way Chemistry for Hong Kong A-Level 3A


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

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.18)

Examples of Non-polar Molecules


with No Net Dipole Moment

41
41

New Way Chemistry for Hong Kong A-Level 3A


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

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.18)

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
42
42

New Way Chemistry for Hong Kong A-Level 3A


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

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.18)

Solubility of Organic Molecules

Hexane in
tetrachloromethane
43
43

Hexane in water

New Way Chemistry for Hong Kong A-Level 3A


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

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.19)

Why does Hexane Dissolve Readily in


Tetrachloromethane?

Intermolecular forces among


hexane molecules and those
among tetrachloromethane
molecules
44
44

Intermolecular forces
between hexane and
tetrachloromethane
molecules

New Way Chemistry for Hong Kong A-Level 3A


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

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.19)

Why is Hexane Insoluble in Water?

45
45

New Way Chemistry for Hong Kong A-Level 3A


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

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.19)

Formation of Hydrogen Bonding


Molecules having OH or NH2 groups
are able to form hydrogen bonds
Hydrogen bonds affect the physical
properties of alcohols and amines with
low molecular masses

46
46

New Way Chemistry for Hong Kong A-Level 3A


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

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.20)

Why does Propan-1-ol have a


Higher Boiling Point?

47
47

New Way Chemistry for Hong Kong A-Level 3A


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

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.20)

Formation of Hydrogen Bonding


Also affect the solubility of a molecule
Molecules with OH groups are able
to form hydrogen bonds with
surrounding water molecules
Soluble in water

48
48

New Way Chemistry for Hong Kong A-Level 3A


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

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.20)

Example 21-4A

Example 21-4B

49
49

New Way Chemistry for Hong Kong A-Level 3A


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

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.21)

Length of Carbon Chains


Molecules with higher molecular masses
have higher m.p., b.p. and density

Higher molecular masses


Large molecular sizes
Stronger London dispersion
forces among molecules

50
50

New Way Chemistry for Hong Kong A-Level 3A


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

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.21)

Length of Carbon Chains


Molecules with branched chains
b.p. and density lower than its
straight-chain isomer
Straight-chain isomers have greater
surface area in contact with each other
Greater attractive force among the
molecules
51
51

New Way Chemistry for Hong Kong A-Level 3A


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

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.21)

Length of Carbon Chains


Molecules with branched chains
m.p. higher than its straight-chain
isomer
Branched-chain isomers are more
spherical
Packed more efficiently in solid state
Extra energy is needed to break
down the efficient packing
52
52

New Way Chemistry for Hong Kong A-Level 3A


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

21.4 Factors Affecting the Physical Properties of Organic Compounds


(SB p.21)

Example 21-4C

Check Point 21-4

53
53

New Way Chemistry for Hong Kong A-Level 3A


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

21.3 Classification of Organic Compounds (SB p.8)


Family
Alkane

General
formula
RH

Functional
group
(Nil)

Example
Formula

IUPAC name

CH3CH3

Ethane

RCH = CH2
Alkene

RCH = CHR
R2C = CHR
R2C = CR2

Alkyne

RC CH
RC CR

CH2 = CH2
Carboncarbon
double bond
CC
CarbonHC CH
carbon triple
bond

Aromatic
ArH
hydrocarbon
54
54

R = CnH2n+1 New Way Chemistry


Phenylforgroup
Hong Kong A-Level 3A
New Way Chemistry for Hong Kong A-Level Book 3A

Ethene

Ethyne

Benzene

21.3 Classification of Organic Compounds (SB p.8)


General
formula

Family

Functional
group
X
halo group

Haloalkane RX
Alcohol

ROH

Ether

Example
Formula

IUPAC name

CH3Cl

Chloromethane

OH
CH3OH
hydroxyl group

O
oxy group

CH3
CH3

Methanol
O

Aldehyde

Methanal
carbonyl group

R = CnH2n+1
55
55

Methoxymethane

New Way Chemistry for Hong Kong A-Level 3A


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

21.3 Classification of Organic Compounds (SB p.8)

Family

General
formula

Functional
group

Example
Formula

Ketone

IUPAC name

Propanone
carbonyl group

Carboxylic
acid

Ethanoic acid
carboxyl group

Amine

Nitrile
56
56

RNH2
R2NH
R 3N
RCN

CH3NH2

Methylamine

amino group

CN
CH3CN
New Way
Chemistry
for Hong Kong A-Level 3A
nitrile
group

R = CnH2n+1 New Way Chemistry for Hong Kong A-Level Book 3A

Ethanenitrile

21.3 Classification of Organic Compounds (SB p.8)


Family

General
formula

Functional
group

Example
Formula

IUPAC name
Methyl
ethanoate

Ester
ester group

Acyl halide
acyl halide
group

Amide
57
57

Ethanoyl
chloride

Ethanamide
New Way amide
Chemistrygroup
for Hong Kong A-Level 3A
New Way Chemistry for Hong Kong A-Level Book 3A

R = CnH2n+1

21.3 Classification of Organic Compounds (SB p.9)

Family

Acid
anhydride

58
58

General
formula

Functional
group

Example
Formula

acid anhydride
group

New Way Chemistry for Hong Kong A-Level 3A


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

IUPAC name

Ethanoic
anhydride

R = CnH2n+1

The END

59
59

New Way Chemistry for Hong Kong A-Level 3A


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