Ch21 (EE)

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

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.

Natural Sources of Organic Compounds

Living
things
Carbohydrates /
Proteins / Fats /
Vitamins /
Antibiotics
A variety of
organic products
obtained from
living things
4
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
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


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


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

21.
2 The Unique
Nature of
Carbon
9
9

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

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

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

Ability to Catenate
C C > Si Si > Ge Ge > Sn Sn
Bond strength as bond length
13
13

Ability to Catenate
CC>NN>OO
Bond strength
as the number of lone pairs
14
14

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

Ability to Form Multiple Bonds

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

16
16


Single bond
Double bond
Triple bond
* X = halogens
17
17

Example 21-2
18
18
Check Point 21-2

21.
3Classification
of Organic
Compounds
19
19

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.

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

Functional Groups
22
22

Functional Groups
23
23
Propane does not react with sodium
Ethanol and propan-1-ol react with

sodium to give hydrogen gas

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

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

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

Structural
formula
The first four members of straight-chain alkanes
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

Structural
formula
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
28
28

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

Homologous Series
Functional group
of an organic
compound
Chemical
properties
Members of a homologous series

have similar chemical properties
30
30

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

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
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
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
34
34
Example 21-3A
Example 21-3B
Example 21-3C
Check Point 21-3

35
35
21.
4
Factors Affecting
the Physical
Properties of
Refer to notes on Bonding and Structure
Organic
pp.77-92 intermolecular forces
Compounds
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


(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


(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


(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


(SB p.18)
Examples of Polar Molecules

with Net Dipole Moment
40
40


(SB p.18)
Examples of Non-polar Molecules

with No Net Dipole Moment
41
41


(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


(SB p.18)
Solubility of Organic Molecules
Hexane in
tetrachloromethane
43
43
Hexane in water


(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


(SB p.19)
Why is Hexane Insoluble in Water?
45
45


(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


(SB p.20)
Why does Propan-1-ol have a

Higher Boiling Point?
47
47


(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


(SB p.20)
Example 21-4A
Example 21-4B
49
49


(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


(SB p.21)

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


(SB p.21)

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


(SB p.21)
Example 21-4C
Check Point 21-4
53
53


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
Ethene
Ethyne
Benzene

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

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

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
R = CnH2n+1
Family
Acid
anhydride
58
58
General
formula
Functional
group
Example
Formula
acid anhydride
group

IUPAC name
Ethanoic
anhydride
R = CnH2n+1
The END
59
59

(a)How was organic chemistry defined

before 1800s?
(a) The knowledge of organic and inorganic
compounds was raised during the 1780s.
Scientists defined organic chemistry as the
study of compounds that could be obtained
from living organisms. They believed that the
synthesis of organic compounds took place in
living organisms only.
60
60

Answer
Back
(b) How is organic chemistry defined

nowadays?
(b) Nowadays, scientists have discovered that
many organic compounds can be synthesized
from inorganic substances. The updated
definition of organic chemistry is the study of
carbon compounds, except for carbon
monoxide, carbon dioxide, carbonates,
hydrogencarbonates, carbides and cyanides.
These compounds have been traditionally
classified under inorganic chemistry.
61
61

Answer
Why is carbon able to catenate?

The ability to catenate of carbon is chiefly due to
the high strength of the C C single bond (bond
enthalpy of C C single bond is 356 kJ mol-1).
Back
62
62

Answer
Would you expect silicon, which is just below

carbon in the Periodic Table, to catenate to form
diverse molecular structures? Explain your
answer.
Answer
Silicon, unlike carbon, does not catenate to form diverse
molecular structures. Carbon is able to catenate because
carbon atoms have a relatively small atomic size. This
enables a carbon atom to form strong covalent bonds
with other carbon atoms. However, due to the greater
atomic size of silicon, its ability to catenate is much lower
than that of carbon.
Back
63
63

Back
Would you expect sulphur, which has an

electronegativity value very close to
carbon, to catenate? Why?
Answer
The electronic configuration of sulphur is 1s22s22p63s23p4. It

has only two unpaired electrons. Its atomic size is larger than
that of carbon. So it has a much lower tendency to catenate
than carbon.
64
64

Identify the functional group(s) in the following

compounds:
(a)
Answer
(a) Carbon-carbon double bond (
chloro group ( Cl)
65
65
) and


compounds:
(b)
Answer
(b) Carbonyl group (
66
66

Back
compounds:
(c)
Answer
(c) Amino group (
(
)
67
67
) and carboxyl group

To which homologous series does each of the

following compounds belong?
(a)
(a) Ester
Answer
68
68


(b)
(b) Amide
Answer
69
69

Back
(c)
(c) Acid anhydride
Answer
70
70

State whether each of the following pairs of

compounds belongs to the same homologous
series. Explain your answer.
(a)
(a) No, the first one is a carboxylic acid and the

second one is an ester.
71
71

Answer

(b)
(b) Yes, both of them are alcohols.
72
72

Answer
Back
(c)
(c) No, the first one is an amide and

the second one is an amine.
73
73

Answer
(a) Name the homologous series of organic

compounds
that contain oxygen atoms in
their functional groups.
(a)
74
74
Alcohol, ether, aldehyde, ketone,

carboxylic acid, ester, acyl halide,
amide and acid anhydride

Answer
(b) Identify and name the functional groups in

glucose which has the following structure.
(b)
OH (hydroxyl group)
and O (oxy
group)
Answer
75
75

Back
(c) Identify and name the functional groups in

the following compounds:
(c)
Br (bromo),
(aldehyde),
(acyl chloride),
(carbon-carbon
double bond) groups
76
76

Answer

(SB p.18)
Why is oil immiscible with water?

Oil molecules do not have free OH groups,
so they cannot form hydrogen bonds with
water molecules.
Back
77
77

Answer

(SB p.20)
The relative molecular mass of glucose is 180.0, but it

is soluble in water. Why?
Glucose molecules have OH groups, so
they are able to form hydrogen bonds with
water molecules. Therefore, glucose is
soluble in water despite it has a high
molecular mass.
78
78
Answer
Back


(SB p.20)
Despite the fact that butan-1-ol and

ethoxyethane have the same relative molecular
mass, they have very different boiling points.
The boiling points of butan-1-ol and
ethoxyethane are 117oC and 35oC respectively.
Explain the difference.
Answer
79
79


(SB p.20)
Back
There is an OH group in butan-1-ol. Thus, butan-1-ol molecules are
able to form hydrogen bonds with one another and the energy required to
separate butan-1-ol molecules would be much greater. Whereas for
ethoxyethane, the attraction among the molecules is weak van der Waals
forces only. The amount of energy required to break the forces would not
be great. Therefore, the boiling point of ethoxyethane is lower than that of
butan-1-ol.
80
80


(SB p.21)
Back
Explain why propan-1-ol is soluble in water but

1-chloropropane is insoluble in water.
Answer
The OH group of propan-1-ol molecules enables it to form

hydrogen bonds with water molecules. Thus it is soluble in water.
Although 1-chloropropane is a polar molecule, it does not form
hydrogen bonds with water molecules. So it is insoluble in water.
81
81


(SB p.21)
Which molecule would have a higher boiling point,

1-bromobutane or 2-bromobutane? Why?
Answer
1-bromobutane would have a higher boiling point.

1-bromobutane is a straight-chain molecule while
2-bromobutane is a branched-chain molecule. Straight-chain
molecules have a greater surface area in contact with each
other, so greater intermolecular forces exist among the
molecules. Higher energy is required to break down the
intermolecular forces among the molecules of 1-bromobutane.
Back
82
82


(SB p.22)
1-Chlorobutane and 2-chloro-2-methylpropane

have the same molecular mass, yet their
melting points differ. The melting point of 1chlorobutane is 123oC while that of 2-chloro2-methylpropane is 27.1oC. Explain the
difference.
Answer
83
83


(SB p.22)
Back
Melting point is a measure of how efficient the molecules are packed

together in the solid state instead of just comparing the van der
Waals forces among molecules. Hence melting point is a function of
the efficient packing of molecules but not the contact surface area.
1-Chlorobutane is a straight-chain molecule while
2-chloro-2-methylpropane is a branched-chain molecule. As
2-chloro-2-methylpropane is more spherical and symmetrical, its
molecules are packed more efficiently in the solid state.
1-Chlorobutane is linear in shape and flattened, its packing in the
solid state is not so efficient. Hence, it has a lower melting point than
2-chloro-2-methylpropane.
84
84


(SB p.24)
(a) What are the major factors that affect the

physical properties of organic compounds?
Answer
(a)
85
85
The physical properties of organic compounds

are mainly affected by the structure of the
functional groups, dipole moment of the
molecule, the formation of hydrogen bonding
between molecules, and the length of carbon
chains of the molecule.


(SB p.24)
(b) The melting point and boiling point of

pentane are
130oC and 36.3oC respectively while the
melting point and boiling point of 2,2dimethylpropane are 15.9oC and 9.5oC
respectively. Account for the difference in
melting point and boiling point between the
two isomers.
Answer
86
86


(SB p.24)
(b)
87
87
Pentane is a straight-chain molecule, while 2,2-dimethylpropane is

a branched-chain molecule. Straight-chain molecules have a
greater surface area in contact with each other than branchedchain molecules. Straight-chain molecules are held together by
stronger intermolecular forces. Therefore, pentane has a higher
boiling point than 2,2-dimethylpropane. Molecules of 2,2dimethylpropane are more spherical in shape and are packed
more efficiently in the solid state. Molecules of pentane are linear
in shape and flattened, so their packing in the solid state is not
efficient. Since extra energy is required to break down the efficient
packing of 2,2-dimethylpropane, 2,2-dimethylpropane has a
higher melting point than pentane.

(SB p.24)
(c) Which molecule, hexane or cyclohexane,

would have a higher melting point? Explain
your answer.
88
88
Answer

(SB p.24)
(c)
89
89
Cyclohexane has a higher melting point than hexane. Molecules

of cyclohexane are more spherical in shape and are packed more
eff iciently in the solid state. Molecules of hexane are linear in
shape and flattened, so their packing in the solid state is not
efficient. Since extra energy is required to break down the efficient
packing of cyclohexane, cyclohexane has a higher melting point
than hexane.


(SB p.24)
(d) Arrange the following molecules in

increasing order of boiling points. Explain
your answer.
90
90
Answer

(SB p.24)
Back
(d)
91
91
The boiling points increase in the order:

butane < propanal < propan-1-ol
Molecules of butane are non-polar. Their molecules are held
together by weak instantaneous dipole-induced dipole
interactions. A relatively small amount of energy is required to
separate the molecules in the process of boiling. Both propanal
and propan-1-ol are polar molecules. Molecules of propanal are
held together by relatively weak dipole-dipole interactions, while
molecules of propan-1-ol are held together by intermolecular
hydrogen bonds. Since the intermolecular forces present in
molecules of propan-1-ol are stronger than those present in
molecules of propanal, a larger amount of energy is required to
separate the propan-1-ol molecules in the process of boiling.

Ch21 (EE)

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21

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

New Way Chemistry for Hong Kong A-Level 3A

21.1 What is Organic Chemistry (SB p.2)

Chemistry of the compounds present

They all contain carbon.

Organic Chemistry is the Chemistry

New Way Chemistry for Hong Kong A-Level 3A

21.1 What is Organic Chemistry (SB p.4)

Natural Sources of Organic Compounds

New Way Chemistry for Hong Kong A-Level 3A

21.1 What is Organic Chemistry (SB p.4)

Natural Sources of Organic Compounds

21.1 What is Organic Chemistry (SB p.3)

Development of Organic Chemistry

New Way Chemistry for Hong Kong A-Level 3A

21.1 What is Organic Chemistry (SB p.3)

Development of Organic Chemistry

New Way Chemistry for Hong Kong A-Level 3A

21.1 What is Organic Chemistry (SB p.3)

Development of Organic Chemistry

New Way Chemistry for Hong Kong A-Level 3A

New Way Chemistry for Hong Kong A-Level 3A

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

Ability to form four strong covalent bonds

Electronic configuration of carbon

Carbon (ground state)

New Way Chemistry for Hong Kong A-Level 3A

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

Ability to form four strong covalent bonds

Each carbon atom has four unpaired

Carbon (excited state)

New Way Chemistry for Hong Kong A-Level 3A

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

New Way Chemistry for Hong Kong A-Level 3A

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

New Way Chemistry for Hong Kong A-Level 3A

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

New Way Chemistry for Hong Kong A-Level 3A

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

n = 1,2,3,(no limit for n)

Only SnH4 (stannane) exists

New Way Chemistry for Hong Kong A-Level 3A

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

Ability to Form Multiple Bonds

Carbon (excited state)

New Way Chemistry for Hong Kong A-Level 3A

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

New Way Chemistry for Hong Kong A-Level 3A

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

Check Point 21-2

New Way Chemistry for Hong Kong A-Level 3A

New Way Chemistry for Hong Kong A-Level 3A

21.3 Classification of Organic Compounds (SB p.7)

Organic compounds are classified by

New Way Chemistry for Hong Kong A-Level 3A

21.3 Classification of Organic Compounds (SB p.7)

New Way Chemistry for Hong Kong A-Level 3A

21.3 Classification of Organic Compounds (SB p.7)

New Way Chemistry for Hong Kong A-Level 3A

21.3 Classification of Organic Compounds (SB p.7)

Propane does not react with sodium

Ethanol and propan-1-ol react with