Introduction To Organic Chemistry

21 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
1
1 New Way Chemistry for Hong Kong A-Level Book 3A
Organic Chemistry
Why is it important?
>90% of compounds are organic
What is an organic compound

• is a compound made from carbon atoms.
• has one or more C atoms.
• has many H atoms.
• may also contain O, S, N, and halogens.
2
Organic Compounds
Typical organic compounds
• have covalent bonds.

• have low melting points.
• have low boiling points.
• are flammable.
• are soluble in nonpolar
solvents.
• are not soluble in water. oil (organic) and
3
water (inorganic)
Organic vs. Inorganic
• Propane, C3H8, is an organic
compound used as a fuel.
• NaCl, salt, is an inorganic

compound composed of Na+
and Cl- ions.
4
Comparing Organic and Inorganic
Compounds
Copyright © 2005 by Pearson Education, Inc.

Publishing as Benjamin Cummings
5
21.1
What is Organic
Chemistry?
6 New Way Chemistry for Hong Kong A-Level 3A

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.

Natural Sources of Organic Compounds

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

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

1
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 Inorganic
Inorganic
compounds
compounds compounds
compounds
obtained from obtained from
living organisms non-living sources

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

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

21.2
The Unique
Nature of Carbon

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)

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)

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

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

Ability to Catenate
C–C>N–N>O–O
Bond strength 
as the number of lone pairs 

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

Ability to Form Multiple Bonds

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

Single bond Double bond Triple bond
* X = halogens

Example 21-2 Check Point 21-

2

21.3
Classification of
Organic
Compounds
21.3 Classification of Organic Compounds (SB p.7)
Functional Groups
• Organic compounds are classified by

the the presence of characteristic
functional groups.

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

Functional Groups

Functional Groups
• 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
Homologous Series
A homologous
A homologous series
series isis aa series
series ofof
compounds that
compounds that have
have the
the same
same functional
functional
group, and
group, and each
each member
member differs
differs from
from
the next
the next member
member byby aa –– CH
CH22 –– unit
unit in
in
their formulae.
their formulae.
CH4 C2H6 C3H8 C4H10
CH2 CH2 CH2

Number of IUPAC Molecular Condensed Structural
carbon name formula structural formula
atom(s) formula
1 Methane CH4 CH4
2 Ethane C2H6 CH3CH3
3 Propane C3H8 CH3CH2CH3
4 Butane C4H10 CH3CH2CH2CH3

The first four members of straight-chain alkanes
Number of IUPAC Molecular Condensed Structural
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
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

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

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

have similar chemical properties

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
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 20°C (g cm–3)
atom(s)
pressure)
CH4
1 Gas –183 –161 –
C2H6
2 Gas –172 –89 –
3 C3H8 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
36 10 Liquid
New Way Chemistry –30
for Hong Kong A-Level Book 3A 174 0.730
C10H22
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 20°C (g cm–3)
atom(s)
pressure)
C11H24
11 Liquid –26 196 0.740
C12H26
12 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
37
37 20
NewSolid 37A-Level
Way Chemistry for Hong Kong 3A 344 0.785
C20H42New Way Chemistry for Hong Kong A-Level Book 3A
Example 21- Example 21-

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

3C

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

(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

(SB p.17)
Structure of Functional Group

Molecule Relative Boiling point
molecular (oC)
mass
Molecules CH3CH2CH2OH 60 97.2
with polar
functional CH3CH2CH2NH2 59 48.6
groups CH3CH2Cl 64.5 12.5
CH3CH2COOH 60 141
Molecules CH3CH2CH2CH3 58 -0.5
with non-
polar CH3CH2CH=CH2 56 -6.2
functional CH3CH2CCH 54 8.1
groups
(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
(SB p.18)
Examples of Polar Molecules

with Net Dipole Moment

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

with No Net Dipole Moment

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

tetrachloromethane
(SB p.19)
Why does Hexane Dissolve Readily in
Tetrachloromethane?
Intermolecular forces among Intermolecular forces

hexane molecules and those  between hexane and
among tetrachloromethane tetrachloromethane
molecules molecules
(SB p.19)
Why is Hexane Insoluble in Water?

(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

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

Higher Boiling Point?

(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

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

(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

(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

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

Example
General Functional
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
–CC–
RC  CH Carbon-
Alkyne HC  CH Ethyne
RC  CR carbon triple
bond
Aromatic
ArH Benzene
hydrocarbon
58 R = CnH2n+1 – New Way Chemistry
Phenylforgroup
Hong Kong A-Level 3A
Example
General Functional
Family
X CH3Cl
Haloalkane RX Chloromethane
halo group
 OH CH3OH
Alcohol ROH Methanol
hydroxyl group
O CH3  O 
Ether RO  R Methoxymethane
oxy group CH3
Aldehyde Methanal
carbonyl group
R = CnH2n+1 –
Example
General Functional
Family
Ketone Propanone
carbonyl group
Carboxylic
Ethanoic acid
acid
carboxyl group
RNH2
Amine R2NH CH3NH2 Methylamine
R 3N amino group
CN
Nitrile RCN CH3CN Ethanenitrile
60 nitrile group
R = CnH2n+1 –New Way Chemistry for Hong Kong A-Level Book 3A
New Way Chemistry for Hong Kong A-Level 3A
60
Example
General Functional
Family
Methyl
Ester
ethanoate
ester group
Ethanoyl
Acyl halide
chloride
acyl halide
group
Amide Ethanamide
61 New Way amide
Chemistrygroup
for Hong Kong A-Level 3A
61 New Way Chemistry for Hong Kong A-Level Book 3A R = CnH2n+1 –
Example
General Functional
Family
Acid Ethanoic
anhydride anhydride
acid anhydride
group R = CnH2n+1 –

The END

(a) How was organic chemistry defined before 1800s?
(a) The knowledge of organic and inorganic

Answer
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.

Back
(b) How is organic chemistry defined nowadays?
(b) Nowadays, scientists have discovered that

Answer
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.

Why is carbon able to catenate?

Answer
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

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

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.

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

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


(b)
Answer
(b) Carbonyl group ( )

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

To which homologous series does each of the following

compounds belong?
(a) (a) Ester
Answer

compounds belong?
(b) (b) Amide
Answer
Back

compounds belong?
(c) (c) Acid anhydride
Answer
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

Answer
second one is an ester.


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

Answer

Back

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

Answer
the second one is an amine.

(a) Name the homologous series of organic compounds

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

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

(b) Identify and name the functional groups in glucose

which has the following structure.
(b) OH (hydroxyl group)

and  O  (oxy
group)
Answer
Back
(c) Identify and name the functional groups in the

following compounds:
(c) Br (bromo),
(aldehyde),
(acyl chloride),
(carbon-carbon
double bond) groups
80 New Way Chemistry for Hong Kong A-Level 3A Answer

(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

(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

(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

(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.

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

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

Answer
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
(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 –123oC while that of 2-
chloro-2-methylpropane is –27.1oC. Explain the difference.
Answer

(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.

(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.

(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 2,2-dimethylpropane are –15.9oC
and 9.5oC respectively. Account for the difference in
melting point and boiling point between the two
isomers.
Answer
(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.
(SB p.24)
(c) Which molecule, hexane or cyclohexane, would have a

higher melting point? Explain your answer.
Answer
(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.

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

boiling points. Explain your answer.
Answer
(SB p.24)
Back
(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.

Introduction To Organic Chemistry

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Introduction To Organic Chemistry

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21 Introduction to

What is an organic compound

• have covalent bonds.

• NaCl, salt, is an inorganic

Copyright © 2005 by Pearson Education, Inc.

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

• Chemistry of the compounds present

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

Natural Sources of Organic Compounds

Natural Sources of Organic Compounds

Fractional distillation / Alkanes /

Check Point 21-

Development of Organic Chemistry

Development of Organic Chemistry

Development of Organic Chemistry

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

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

Ability to form four strong covalent bonds

• Electronic configuration of carbon

Carbon (ground state)

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

Ability to form four strong covalent bonds

• Each carbon atom has four unpaired

• Tend to form four strong covalent bonds

Carbon (excited state)

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

• Carbon atoms link together to form

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

C – C > Si – Si > Ge – Ge > Sn – Sn

Bond strength  as bond length 

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

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

CnH2n+2 n = 1,2,3,…(no limit for n)

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

Ability to Form Multiple Bonds

Carbon (excited state)

Single bond Double bond Triple bond

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

Example 21-2 Check Point 21-

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

• Organic compounds are classified by

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

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

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

• Propane does not react with sodium

• Ethanol and propan-1-ol react with

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

• have similar chemical properties

CH4 C2H6 C3H8 C4H10

CH2 CH2 CH2

2 Ethane C2H6 CH3CH3

3 Propane C3H8 CH3CH2CH3

4 Butane C4H10 CH3CH2CH2CH3

30 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

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

alkanoic acids: CnH2n+1COOH

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

Members of a homologous series

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