Introduction To Organic Chemistry

New Way Chemistry for Hong Kong A-Level Book 3A
1
1
Introduction to
Organic Chemistry
21.1 What is Organic Chemistry?
21.2 The Unique Nature of Carbon
21.3 Classification of Organic Compounds
21.4 Factors Affecting the Physical Properties of
Organic Compounds
21

2
New Way Chemistry for Hong Kong A-Level 3A
2
21.1
What is Organic
Chemistry?

3
3
21.1 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.

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

5
5
Crude oil
or coal
Fractional distillation /
destructive distillation
Alkanes /
Alkenes /
Alkynes /
Aromatic
hydrocarbons
Natural Sources of Organic Compounds
A variety of
useful products
derived from
crude oil and coal
Check Point 21-1

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

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

8
8
Redefining ...
Organic chemistry is the study of carbon
compounds (except CO, CO
2
, carbonates,
hydrogencarbonates, carbides and cyanides)
obtained from natural sources or
synthesized in the laboratories.
as a Science

9
9
21.2
The Unique
Nature of Carbon

10
10
21.2 The Unique Nature of Carbon (SB p.5)
Ability to form four strong covalent bonds
Carbon (ground state)
Electronic configuration of carbon
(ground state) : 1s
2
2s
2
2p
2

11
11
Each carbon atom has four unpaired
electrons when excited
Tend to form four strong covalent bonds
Carbon (excited state)
Ability to form four strong covalent bonds

12
12
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
Ability to Catenate

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

14
14
Ability to Catenate
C C > N N > O O
Bond strength
as the number of lone pairs

15
15
Ability to Catenate
C
n
H
2n+2
n = 1,2,3,(no limit for n)
Si
n
H
2n+2
n = 1 to 6 only silanes
Ge
n
H
2n+2
n = 1 to 3 only germanes
Sn
n
H
2n+2
Only SnH
4
(stannane) exists

16
16
Carbon (excited state)
Ability to Form Multiple Bonds
sp
2 bonds, 2 bonds
sp
2

1 bond, 3 bonds
sp
3

4 bonds

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

18
18
Example 21-2
Check Point 21-2

19
19
21.3
Classification of
Organic
Compounds

20
20
Organic compounds are classified by
the the presence of characteristic
functional groups.
21.3 Classification of Organic Compounds (SB p.7)
Functional Groups

21
21
A functional group is defined as an
atom or a group of atoms that
effectively determines the chemical
properties of an organic compound.
Functional Groups

22
22
Functional Groups

23
23
Functional Groups
Propane does not react with sodium
Ethanol and propan-1-ol react with
sodium to give hydrogen gas

24
24
have similar chemical properties
they contain the same functional group OH
they are classified into the same
homologous series alcohols
and
Functional Groups

25
25
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 CH
2
unit in
their formulae.
CH
4
C
2
H
6
C
3
H
8
C
4
H
10

CH
2
CH
2
CH
2

26
26
Number
of carbon
atom(s)
IUPAC
name
Molecular
formula
Condensed
structural
formula
Structural
formula
1 Methane CH
4
CH
4

2 Ethane C
2
H
6
CH
3
CH
3

3 Propane C
3
H
8
CH
3
CH
2
CH
3

4 Butane C
4
H
10
CH
3
CH
2
CH
2
CH
3

The first four members of straight-chain alkanes

27
27
Number
of carbon
atom(s)
IUPAC
name
Molecular
formula
Condensed
structural
formula
Structural
formula
1 Methanol CH
3
OH

CH
3
OH

2 Ethanol C
2
H
5
OH

CH
3
CH
2
OH

3 Propan-1-
ol
C
3
H
7
OH CH
3
CH
2
CH
2
OH

4 Butan-1-
ol
C
4
H
9
OH

CH
3
CH
2
CH
2
CH
2
OH

The first four members of straight-chain alcohols

28
28
Members in the same series can be
represented by a general formula.
e.g. alkanes: C
n
H
2n+2

alkenes: C
n
H
2n

alkynes: C
n
H
2n-2

Homologous Series

29
29
Members in the same series can be
represented by a general formula.
Homologous Series
e.g. alkanols: C
n
H
2n+1
OH
alkanals: C
n
H
2n+1
CHO
alkanoic acids: C
n
H
2n+1
COOH

30
30
Functional group
of an organic
compound
Chemical
properties
Members of a homologous series
have similar chemical properties
Homologous Series

31
31
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
Homologous Series

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

C
2
H
6
C
3
H
8
C
4
H
10
C
5
H
12
C
6
H
14
C
7
H
16
C
8
H
18
C
9
H
20
C
10
H
22
Gas
Gas
Gas
Gas
Liquid
Liquid
Liquid
Liquid
Liquid
Liquid
183
172
188
135
130
95
91
57
54
30
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

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33
Number
of
carbon
atom(s)
Molecular
formula
State (at
room
temperature
and
pressure)
Melting
point (C)
Boiling
point (C)
Density of
solid / liquid at
20C (g cm
3
)
11
12
13
14
15
16
17
18
19
20
C
11
H
24

C
12
H
26
C
13
H
28
C
14
H
30
C
15
H
32
C
16
H
34
C
17
H
36
C
18
H
38
C
19
H
40
C
20
H
42
Liquid
Liquid
Liquid
Liquid
Liquid
Liquid
Liquid
Solid
Solid
Solid
26
10
7
3
10
18
22
28
32
37
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
Some physical properties of the first 20 members of
straight-chain alkanes

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

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21.4
Factors Affecting the
Physical Properties of
Organic Compounds
Refer to notes on Bonding and Structure
pp.77-92 intermolecular forces

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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)
21.4 Factors Affecting the Physical Properties of Organic Compounds
(SB p.17)
Main Factors Affecting the
Physical Properties of Organic
Compounds

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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
(SB p.17)
Structure of Functional Group

38
38
(SB p.17)
Structure of Functional Group
Molecule Relative
molecular
mass
Boiling point
(
o
C)
Molecules
with polar
functional
groups
CH
3
CH
2
CH
2
OH 60 97.2
CH
3
CH
2
CH
2
NH
2
59 48.6
CH
3
CH
2
Cl 64.5 12.5
CH
3
CH
2
COOH 60 141
Molecules
with non-
polar
functional
groups
CH
3
CH
2
CH
2
CH
3
58 -0.5
CH
3
CH
2
CH=CH
2
56 -6.2
CH
3
CH
2
CCH 54 8.1

39
39
(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

40
40
(SB p.18)
Examples of Polar Molecules
with Net Dipole Moment

41
41
(SB p.18)
Examples of Non-polar Molecules
with No Net Dipole Moment

42
42
(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

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

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44
(SB p.19)
Why does Hexane Dissolve Readily in
Tetrachloromethane?
Intermolecular forces among
hexane molecules and those
among tetrachloromethane
molecules

Intermolecular forces
between hexane and
tetrachloromethane
molecules

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

46
46
(SB p.19)
Formation of Hydrogen Bonding
Molecules having OH or NH
2
groups
are able to form hydrogen bonds
Hydrogen bonds affect the physical
properties of alcohols and amines with
low molecular masses

47
47
(SB p.20)
Why does Propan-1-ol have a
Higher Boiling Point?

48
48
(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

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

50
50
(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

51
51
(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

52
52
(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

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

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54
Family
General
formula
Functional
group
Example
Formula IUPAC name
Alkane RH (Nil) CH
3
CH
3
Ethane
Alkene
RCH = CH
2
RCH = CHR
R
2
C = CHR
R
2
C = CR
2

Carbon-
carbon
double bond
CH
2
= CH
2
Ethene
Alkyne
RC CH
RC CR
C C
Carbon-
carbon triple
bond
HC CH Ethyne
Aromatic
hydrocarbon
ArH

Phenyl group
Benzene
R = C
n
H
2n+1


55
55
Family
General
formula
Functional
group
Example
Formula IUPAC name
Haloalkane RX
X
halo group
CH
3
Cl Chloromethane
Alcohol ROH
OH
hydroxyl group
CH
3
OH Methanol
Ether RO R
O
oxy group
CH
3
O
CH
3
Methoxymethane
Aldehyde

carbonyl group
Methanal
R = C
n
H
2n+1


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56
Family
General
formula
Functional
group
Example
Formula IUPAC name
Ketone

carbonyl group
Propanone
Carboxylic
acid

carboxyl group
Ethanoic acid
Amine
RNH
2

R
2
NH
R
3
N

amino group
CH
3
NH
2
Methylamine
Nitrile RCN
C N
nitrile group
CH
3
CN Ethanenitrile
R = C
n
H
2n+1


57
57
Family
General
formula
Functional
group
Example
Formula IUPAC name
Ester

ester group
Methyl
ethanoate
Acyl halide

acyl halide
group
Ethanoyl
chloride
Amide

amide group
Ethanamide
R = C
n
H
2n+1


58
58
Family
General
formula
Functional
group
Example
Formula IUPAC name
Acid
anhydride

acid anhydride
group
Ethanoic
anhydride
R = C
n
H
2n+1


59
59
The END

60
60
(a) How was organic chemistry defined before 1800s?
Answer
(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.

61
61
(b) How is organic chemistry defined nowadays?
Back
Answer
(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.

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

63
63
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

64
64
Would you expect sulphur, which has an
electronegativity value very close to carbon, to
catenate? Why?
Back
Answer
The electronic configuration of sulphur is 1s
2
2s
2
2p
6
3s
2
3p
4
. 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.

65
65
Identify the functional group(s) in the following compounds:
(a)

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


66
66
(b)

Answer
(b) Carbonyl group ( )


67
67
(c)

Answer
(c) Amino group ( ) and carboxyl group ( )

Back

68
68
To which homologous series does each of the following
compounds belong?
(a)

Answer
(a) Ester

69
69
compounds belong?
(b)

Answer
(b) Amide

70
70
compounds belong?
(c)

Answer
(c) Acid anhydride
Back

71
71
State whether each of the following pairs of compounds
belongs to the same homologous series. Explain your answer.
(a)

Answer
(a) No, the first one is a carboxylic acid and the
second one is an ester.

72
72
(b)

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

73
73
(c)

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

74
74
(a) Name the homologous series of organic compounds
that contain oxygen atoms in their functional groups.
Answer
(a) Alcohol, ether, aldehyde, ketone,
carboxylic acid, ester, acyl halide,
amide and acid anhydride

75
75
(b) Identify and name the functional groups in glucose
which has the following structure.

Answer
(b) OH (hydroxyl group)
and O (oxy group)

76
76
(c) Identify and name the functional groups in the
following compounds:

Answer
Back
(c) Br (bromo),

(aldehyde),

(acyl chloride),

(carbon-carbon
double bond) groups


77
77
(SB p.18)
Why is oil immiscible with water?
Answer
Oil molecules do not have free OH groups,
so they cannot form hydrogen bonds with
water molecules.
Back

78
78
(SB p.20)
The relative molecular mass of glucose is 180.0, but it
is soluble in water. Why?
Answer
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.
Back

79
79
(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 117
o
C and 35
o
C respectively. Explain the
difference.
Answer

80
80
(SB p.20)
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.

Back

81
81
(SB p.21)
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.
Back

82
82
(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

83
83
(SB p.22)
1-Chlorobutane and 2-chloro-2-methylpropane have the
same molecular mass, yet their melting points differ. The
melting point of 1-chlorobutane is 123
o
C while that of 2-
chloro-2-methylpropane is 27.1
o
C. Explain the difference.

Answer

84
84
(SB p.22)
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.
Back

85
85
(SB p.24)
(a) What are the major factors that affect the physical
properties of organic compounds?
Answer
(a) 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.

86
86
(SB p.24)
(b) The melting point and boiling point of pentane are
130
o
C and 36.3
o
C respectively while the melting point
and boiling point of 2,2-dimethylpropane are 15.9
o
C
and 9.5
o
C respectively. Account for the difference in
melting point and boiling point between the two
isomers.

Answer

87
87
(SB p.24)
(b) 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 branched-
chain molecules. Straight-chain molecules are held together by
stronger intermolecular forces. Therefore, pentane has a higher
boiling point than 2,2-dimethylpropane. Molecules of 2,2-
dimethylpropane 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.

88
88
(SB p.24)
(c) Which molecule, hexane or cyclohexane, would have a
higher melting point? Explain your answer.

Answer

89
89
(SB p.24)
(c) 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.

90
90
(SB p.24)
(d) Arrange the following molecules in increasing order of
boiling points. Explain your answer.

Answer

91
91
(SB p.24)
(d) 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.
Back

Introduction To Organic Chemistry

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