Chapter 13

Unsaturated
Hydrocarbons
 Chapter 13

Table of Contents

13.1 Unsaturated hydrocarbons

13.2 Characteristics of alkenes and cycloalkenes
13.3 Nomenclature for alkenes and cycloalkenes
13.4 Line-angle structural formulas for alkenes
13.5 Constitutional isomerism in alkenes
13.6 Cis-trans isomerism in alkenes
13.7 Naturally occurring alkenes
13.8 Physical properties of alkenes and cycloalkenes
13.9 Preparation of alkenes
13.10 Chemical reactions of alkenes
13.11 Polymerization of alkenes: Addition polymers
13.12 Alkynes
13.13 Aromatic hydrocarbons
13.14 Nomenclature for aromatic hydrocarbons
13.15 Properties of and sources for aromatic hydrocarbons
13.16 Fused-ring aromatic hydrocarbons

Copyright ©2016 Cengage Learning. All Rights Reserved. 2

 Section 13.1

Unsaturated Hydrocarbons

• Unsaturated hydrocarbon: A Hydrocarbon with one or

more carbon–carbon multiple bonds
– Physical properties are similar to those of saturated
hydrocarbons
– Chemical properties are distinct
– Chemically more reactive than saturated
hydrocarbons
– Reactivity of unsaturated hydrocarbons is due
carbon–carbon multiple bond(s)

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 3

 Section 13.1

Unsaturated Hydrocarbons

Functional Group
• Structural feature of an organic molecule that is directly
involved in most of its chemical reactions
• Carbon–carbon double/triple bonds are the functional
groups in unsaturated hydrocarbons
• Subdivided into 3 groups:
– Alkenes - Contain one or more carbon–carbon double bonds
– Alkynes - Contain one or more carbon–carbon triple bonds
– Aromatic hydrocarbons - Exhibit a special type of
“delocalized” bonding involving a six-membered carbon ring

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 4

 Section 13.1

Unsaturated Hydrocarbons

An unsaturated hydrocarbon is:

a. A hydrocarbon in which multiple bonds are present with
the general formula of CnH2n+2.
b. A hydrocarbon in which one or more carbon-carbon
multiple bonds are present.
c. A hydrocarbon that does not contain all the possible
number of hydrogen atoms.
d. Both (b) and (c).

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 5

 Section 13.1

Unsaturated Hydrocarbons

An unsaturated hydrocarbon is:

a. A hydrocarbon in which multiple bonds are present with
the general formula of CnH2n+2.
b. A hydrocarbon in which one or more carbon-carbon
multiple bonds are present.
c. A hydrocarbon that does not contain all the possible
number of hydrogen atoms.
d. Both (b) and (c).

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 6

 Section 13.2

Characteristics of Alkenes and Cycloalkenes

Alkanes
• Acyclic unsaturated hydrocarbons that contain one or
more carbon–carbon double bonds
• Functional group - C=C group
• Names end with an -ene versus -ane
– -ene signifies the presence of a double bond
• General molecular formula - CnH2n
– Alkanes with one carbon–carbon bond
• Two of the simplest alkenes are ethene and propene

CH CH CH CH CH
2 2 2 2 3

Ethene Propene
Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 7

 Section 13.2

Characteristics of Alkenes and Cycloalkenes

Fig 13.1 - Representations of Ethene and Methane

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 8

 Section 13.2

Characteristics of Alkenes and Cycloalkenes

Cycloalkenes
• Cyclic unsaturated hydrocarbons with one or more
carbon–carbon double bonds within the ring system
• Those with one double bond have the general molecular
formula CnH2n-2
• Cyclopropene (C3H4) is the simplest cycloalkane
– Three-membered carbon ring system with one double
bond
• Those with more than one double bond are relatively
common

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 9

 Section 13.2

Characteristics of Alkenes and Cycloalkenes

Hydrocarbons containing one or more carbon–

carbon double bonds are known as:
a. Multiple bond alkanes
b. Multiple bond cycloalkanes
c. Alkenes
d. Alkynes

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 10

 Section 13.2

Characteristics of Alkenes and Cycloalkenes

Hydrocarbons containing one or more carbon–

carbon double bonds are known as:
a. Multiple bond alkanes
b. Multiple bond cycloalkanes
c. Alkenes
d. Alkynes

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 11

 Section 13.3

Nomenclature for Alkenes and Cycloalkenes

IUPAC Rules
• Rule 1
– Replace the alkane suffix -ane with the suffix -ene
• Rule 2
– Select as the parent carbon chain the longest continuous
chain of carbon atoms that contains both carbon atoms of
the double bond
• Rule 3
– Number the parent carbon chain beginning at the end
nearest to the double bond

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 12

 Section 13.3

Nomenclature for Alkenes and Cycloalkenes

IUPAC Rules
• Rule 4
‒ Give the position of the double bond in the chain as a
single number, which is the lower-numbered carbon atom
participating in the double bond
• Rule 5
‒ Use the suffixes -diene, -triene, -tetrene, and so on when
more than one double bond is present in the molecule
• Rule 6
‒ A number is not needed to locate the double bond in
unsubstituted cycloalkenes with only one double bond
because that bond is assumed to be between carbons 1
and 2
Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 13

 Section 13.3

Nomenclature for Alkenes and Cycloalkenes

IUPAC Rules
• Rule 7
– In substituted cycloalkenes with only one double bond, the
double-bonded carbon atoms are numbered 1 and 2 in the
direction (clockwise or counterclockwise) that gives the
first-encountered substituent the lower number
• Rule 8
– In cycloalkenes with more than one double bond within the
ring, assign one double the numbers 1 and 2 and the other
double bonds the lowest numbers possible

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 14

 Section 13.3

Nomenclature for Alkenes and Cycloalkenes

Practice Exercise
Assign IUPAC names to the f ollowing alkenes and cycloalkenes
H2 H
a. H 3C C C C C CH3 b.
H H

CH3

b. H 2C C C CH2 d.
c. H H

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 15

 Section 13.3

Nomenclature for Alkenes and Cycloalkenes

Practice Exercise
Assign IUPAC names to the f ollowing alkenes and cycloalkenes
H2 H
a. H 3C C C C C CH3 b.
H H

CH3

b. H 2C C C CH2 d.
c. H H

Answers:

a. 5-Methyl-2-hexene

b. 3-Ethyl-4-methylcyclohexene

c. 1,3-Butadiene Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 16

 Section 13.3

Nomenclature for Alkenes and Cycloalkenes

Common Names (Non-IUPAC Names)

• Common names are used mostly for compounds
• Two most common names for alkenes are:
– Ethylene (IUPAC name – Ethene)
• CH2 CH2
– Propylene (IUPAC name – Propene)
• CH2 CH CH3

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 17

 Section 13.3

Nomenclature for Alkenes and Cycloalkenes

Alkenes as Substituents
• Alkenyl group: A noncyclic hydrocarbon substituent in
which a carbon double bond is present
• Most frequently encountered alkenyl groups
– Methylidene (one-carbon)
• Common name - Methylene
– Ethenyl (two-carbon)
• Common name - Vinyl
– 2-propenyl (three-carbon)
• Common name - Allyl

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 18

 Section 13.3

Nomenclature for Alkenes and Cycloalkenes

The parent chain of a compound containing

carbon-carbon double bonds ends with the suffix:
a. -ane
b. -ene
c. -yne
d. -ayne

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 19

 Section 13.3

Nomenclature for Alkenes and Cycloalkenes

The parent chain of a compound containing

carbon-carbon double bonds ends with the suffix:
a. -ane
b. -ene
c. -yne
d. -ayne

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 20

 Section 13.4

Line-Angle Structural Formulas for Alkenes

Alkene and Cycloalkene Structures

• Line-angle formulas for the three- to six-carbon acyclic 1-
alkenes are:

Propene 1-Butene 1-Pentene 1-Hexene

• Representative line-angle structural formulas for

substituent-bearing alkenes are:
6 4 2
5 3 1
5 3 1
4 2

3,5-dimethyl-1-hexene 2-Ethyl-3-methyl-1-pentente Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 21

 Section 13.4

Line-Angle Structural Formulas for Alkenes

Alkene and Cycloalkene Structures

• Diene representations on terms of line-angle structural
formulas are:

1,4-Pentadiene 2-Methyl-1,3-butadiene

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 22

 Section 13.4

Line-Angle Structural Formulas for Alkenes

Which of the following is a line-angle structural

formula for 1,3-butadiene?

a. b.

c. d.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 23

 Section 13.4

Line-Angle Structural Formulas for Alkenes

Which of the following is a line-angle structural

formula for 1,3-butadiene?

a. b.

c. d.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 24

 Section 13.5

Constitutional Isomerism in Alkenes

• There are more alkene isomers possible for a given

number of carbon atoms than there are alkane isomers
• Skeletal isomers: Constitutional isomers that possess
different carbon-atom arrangements and that contain
identical functional groups if functional groups are
present
• Positional isomers: Constitutional isomers that possess
the same carbon-atom arrangement and that have
differing locations for functional groups present

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 25

 Section 13.5

Constitutional Isomerism in Alkenes

1-butene and 2-butene are examples of:

a. Positional isomers.
b. Positional skeletal isomers.
c. Skeletal isomers.
d. Both (a) and (b)

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 26

 Section 13.5

Constitutional Isomerism in Alkenes

1-butene and 2-butene are examples of:

a. Positional isomers.
b. Positional skeletal isomers.
c. Skeletal isomers.
d. Both (a) and (b)

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 27

 Section 13.6

Cis-Trans Isomerism in Alkenes

• Cis–trans isomerism in alkenes results from the

structural rigidity associated with C=C bonds
• Rotation about C=C (or CΞC) is not possible

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 28

 Section 13.6

Cis-Trans Isomerism in Alkenes

Cis-Trans Isomers
• Cis and trans isomers are isomers that exist when each of the
two carbons of the double bond has two different groups
attached to it
– Cis-isomer
• The two groups are located on the same side of double
bond
– Trans-isomer
• The two groups are located on opposite sides of the double
bond

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 29

 Section 13.6

Cis-Trans Isomerism in Alkenes

Practice Exercise

• Identify the following as cis isomers, trans isomers, or

neither:
H2
H 3C C H

H Cl

H 3C H
H H

H2
H 3C C H

Cl H Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 30

 Section 13.6

Cis-Trans Isomerism in Alkenes

Practice Exercise

• Identify the following as cis isomers, trans isomers, or

neither:
H2
H 3C C H
Trans
H Cl

H 3C H
Neither
H H

H2
H 3C C H Neither

Cl H Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 31

 Section 13.6

Cis-Trans Isomerism in Alkenes

Which of the following factors favour the existence

of cis–trans isomers in alkenes?
a. There is a lack of rotation about a double bond.
b. Each of the two carbons of the double bond has two
different groups attached to it.
c. Do not exist because of the double-bonded carbons
bears two identical groups.
d. All of these.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 32

 Section 13.6

Cis-Trans Isomerism in Alkenes

Which of the following factors favour the existence

of cis–trans isomers in alkenes?
a. There is a lack of rotation about a double bond.
b. Each of the two carbons of the double bond has two
different groups attached to it.
c. Do not exist because of the double-bonded carbons
bears two identical groups.
d. All of these.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 33

 Section 13.7

Naturally Occurring Alkenes

Pheromones
• Pheromone: A compound secreted or excreted by
insects (and some animals and plants) that triggers a
response in other members of the same species
• Many pheromones have alkene structures
– Arrangement of double bonds (cis or trans) influences
the biological activity of alkene-type pheromones
• Example - The sexual attractant of the female silkworm
is a 16-carbon alkene derivative containing an –OH
group

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 34

 Section 13.7

Naturally Occurring Alkenes

Terpenes
• Organic compounds whose carbon skeleton comprises
two or more 5-carbon isoprene structural units
• Isoprene (2-methyl-1,3-butadiene) is a five-carbon diene
• Terpenes are widely distributed in nature
– More than 22,000 terpenes are found in biological systems
and
– They are responsible for the characteristic odors of many
trees and plant fragrances

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 35

 Section 13.7

Naturally Occurring Alkenes

Figure 13.5 - Terpenes

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 36

 Section 13.7

Naturally Occurring Alkenes

When you subject ants to the destructive process

known as steam distillation, a naturally occurring
alkene is obtained. When a small amount of this
alkene is placed on the ground, it attracts many
ants. What is the name of this alkene?
a. Pheromone
b. Hormone
c. Terpene
d. No compounds like this exist.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 37

 Section 13.7

Naturally Occurring Alkenes

When you subject ants to the destructive process

known as steam distillation a naturally occurring
alkene is obtained. When a small amount of this
alkene is placed on the ground it attracts many
ants; therefore it is known as a:
a. Pheromone
b. Hormone
c. Terpene
d. No compounds like this exist.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 38

 Section 13.8

Physical Properties of Alkenes and Cycloalkenes

• Physical properties are similar to those of alkanes

• The melting point of an alkene is usually lower than that
of an alkane with same number of carbon atoms
• Alkenes with 2 to 4 carbon atoms are gases at room
temperature
• Unsubstituted alkenes with 5 to 17 carbon atoms are
liquids
• Alkenes with more than 17 carbon atoms are solids

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 39

 Section 13.8

Physical Properties of Alkenes and Cycloalkenes

Figure 13.7 - A Physical-State Summary for Unbranched

Cycloalkanes and Unsubstituted Cycloalkanes

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 40

 Section 13.8

Physical Properties of Alkenes and Cycloalkenes

Alkenes have similar physical properties as

alkanes except alkenes usually have _____
melting points than an alkane with the same
number of carbon atoms.
a. Identical
b. Higher
c. Lower
d. This is determined by where the double bond is located.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 41

 Section 13.8

Physical Properties of Alkenes and Cycloalkenes

Alkenes have similar physical properties as

alkanes except alkenes usually have _____
melting points than an alkane with the same
number of carbon atoms.
a. Identical
b. Higher
c. Lower
d. This is determined by where the double bond is located.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 42

 Section 13.9

Preparation of Alkenes

• Dehydrogenation reaction: A reaction characterized by

the loss of a hydrogen atom from each of two adjacent
carbon atoms, forming a carbon–carbon double bond
– Alkenes are not easily formed from alkanes
• Special catalysts and a temperature of 500°C required
• Easier alkene-producing methods exist
– Dehydration of alcohol

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 43

 Section 13.9

Preparation of Alkenes

A dehydrogenation reaction is characterized by:

a. The formation of a carbon–carbon triple bond.
b. An increase of three hydrogen atoms and the formation of a
carbon–carbon double bond.
c. The loss of one hydrogen atom from each of two adjacent
carbon atoms, forming a carbon–carbon double bond.
d. The loss of five hydrogen atoms from one carbon atom
forming a carbon–carbon triple bond.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 44

 Section 13.9

Preparation of Alkenes

A dehydrogenation reaction is characterized by:

a. The formation of a carbon–carbon triple bond.
b. An increase of three hydrogen atoms and the formation of a
carbon–carbon double bond.
c. The loss of one hydrogen atom from each of two adjacent
carbon atoms, forming a carbon–carbon double bond.
d. The loss of five hydrogen atoms from one carbon atom
forming a carbon–carbon triple bond.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 45

 Section 13.10

Chemical Reactions of Alkenes

Chemical Properties
• Alkenes are very flammable
– Combustion products are carbon dioxide and water
• Addition reaction: A reaction in which atoms or group of
atoms are added to each carbon atom of a carbon–
carbon multiple bond in a hydrocarbon or hydrocarbon
derivative

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 46

 Section 13.10

Chemical Reactions of Alkenes

Alkenes undergo _____ reactions.

a. Elimination
b. Addition
c. Substitution
d. Decomposition

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 47

 Section 13.10

Chemical Reactions of Alkenes

Alkenes undergo _____ reactions.

a. Elimination
b. Addition
c. Substitution
d. Decomposition

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 48

 Section 13.10

Chemical Reactions of Alkenes

Figure 13.8 - Alkene Addition Reaction

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 49

 Section 13.10

Chemical Reactions of Alkenes

Symmetrical Addition Reactions

• Hydrogenation reaction
– In alkene hydrogenation, a hydrogen atom is added to
each carbon atom of a double bond
• Catalyst is usually Ni or Pt
• Halogenation reaction
– In alkene halogenation, a halogen atom is added to
each carbon atom of a double bond
• No catalyst required

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 50

 Section 13.10

Chemical Reactions of Alkenes

Unsymmetrical Addition Reactions

• Markovnikov’s rule: When an unsymmetrical molecule
of the form of HQ reacts with an unsymmetrical alkene,
the hydrogen atom from the HQ becomes attached to
the unsaturated carbon atom that already has the most
hydrogen atoms

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 51

 Section 13.10

Chemical Reactions of Alkenes

The addition of HCl and H2O, known as hydrohalogen

and hydration, respectively, to an alkene follows
Markovnikov’s rule which states that:
a. The hydrogen of either attaches to the unsaturated carbon
that has the most hydrogen atoms.
b. The hydrogen of either attaches to the unsaturated carbon
that has the least hydrogen atoms.
c. The halogen or OH- of water attaches to the unsaturated
carbon that has the most hydrogen atoms.
d. The addition of the hydrogen is a random process that
depends on the location of the carbon-carbon double bond.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 52

 Section 13.10

Chemical Reactions of Alkenes

The addition of HCl and H2O, known as hydrohalogen

and hydration, respectively, to an alkene follows
Markovnikov’s rule which states that:
a. The hydrogen of either attaches to the unsaturated carbon
that has the most hydrogen atoms.
b. The hydrogen of either attaches to the unsaturated carbon
that has the least hydrogen atoms.
c. The halogen or OH- of water attaches to the unsaturated
carbon that has the most hydrogen atoms.
d. The addition of the hydrogen is a random process that
depends on the location of the carbon-carbon double bond.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 53

 Section 13.11

Polymerization of Alkenes: Addition Polymers

• Polymer: A large molecule formed by the repetitive

bonding together of many smaller molecules
• Addition polymer: A polymer in which the monomers
simply “add together” with no other products formed
besides the polymer
– It is similar to the addition reactions described
previously except that there is no reactant other than
the alkene or substituted alkene
• Example - Formation of polyethylene

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 54

 Section 13.11

Polymerization of Alkenes: Addition Polymers

• Polymers cannot be accurately represented by an exact

formula
– Length of carbon chains vary with each polymer
molecule
• The notation used is independent of the carbon-chain
length

H H

C C

H H
n

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 55

 Section 13.11

Polymerization of Alkenes: Addition Polymers

Figure 13.12 - Ethene-Based Polymers

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 56

 Section 13.11

Polymerization of Alkenes: Addition Polymers

Butadiene-Based Addition Polymers

• When dienes are used as monomers in addition
polymerization reactions, the resulting polymers contain
double bonds
– Double bonds are still unsaturated
• They are more flexible than ethane-based saturated
polymers

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 57

 Section 13.11

Polymerization of Alkenes: Addition Polymers

Addition Copolymers
• Copolymers: Polymers in which two different monomers
are present
• Examples
– Saran Wrap
• Chloroethene (vinyl chloride) and 1,1-dichloroethene
– Styrene–butadiene rubber
• 1,3-butadiene and styrene in a 3:1 ratio

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 58

 Section 13.11

Polymerization of Alkenes: Addition Polymers

The small unit that is a repeating unit in a polymer is

known as a(n):
a. Repeating alkene.
b. Addition alkene.
c. Monomer.
d. Monomeric alkene.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 59

 Section 13.11

Polymerization of Alkenes: Addition Polymers

The small unit that is a repeating unit in a polymer is

known as a(n):
a. Repeating alkene.
b. Addition alkene.
c. Monomer.
d. Monomeric alkene.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 60

 Section 13.12

Alkynes

• Alkyne: An acyclic unsaturated hydrocarbon that

contains one or more carbon–carbon triple bonds
– Alkyne functional group is a CΞC group
• Names end with the suffix -yne
• The general formula is CnH2n–2
• Examples
– C2H2
– C3H4

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 61

 Section 13.12

Alkynes

• Nomenclature for alkynes

– The rules for naming alkynes are identical to those
used to name alkenes, except the ending -yne is used
instead of -ene
• Isomerism and alkynes
– Cis–trans isomerism is not possible due to the
linearity (180º angles) about an alkyne’s triple bond
– Constitutional isomers are possible
• Relative to the carbon chain (skeletal isomers) and to
the position of the triple bond (positional isomers)

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 62

 Section 13.12

Alkynes

Properties of Alkynes
• Similar to those of alkenes and alkanes
• Insoluble in water but soluble in organic solvents
• Densities less than that of water
• Boiling points increase with molecular mass
• Low-molecular-mass alkynes are gases at room
temperature

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 63

 Section 13.12

Alkynes

An alkyne is a(n):
a. Cyclic unsaturated hydrocarbon that contains one or
more carbon-carbon double bonds.
b. Cyclic unsaturated hydrocarbon that contains one or
more carbon-carbon triple bonds.
c. Acyclic unsaturated hydrocarbon that contains two or
more carbon-carbon double bonds.
d. Acyclic unsaturated hydrocarbon that contains one or
more carbon-carbon triple bonds.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 64

 Section 13.12

Alkynes

An alkyne is a(n):
a. Cyclic unsaturated hydrocarbon that contains one or
more carbon-carbon double bonds.
b. Cyclic unsaturated hydrocarbon that contains one or
more carbon-carbon triple bonds.
c. Acyclic unsaturated hydrocarbon that contains two or
more carbon-carbon double bonds.
d. Acyclic unsaturated hydrocarbon that contains one or
more carbon-carbon triple bonds.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 65

 Section 13.13

Aromatic Hydrocarbons

Bonding in Hydrocarbons
• Benzene
– Possesses a six-membered carbon ring represented
using one of the following structures

– Equivalent nature of C–C bonds is aptly described

using an average of the two structures
• An alternative that uses a single structure is:

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 66

 Section 13.13

Aromatic Hydrocarbons

An aromatic hydrocarbon consists of:

a. A six carbon member ring containing one or more
double bonds.
b. A six carbon member ring containing two or more
double bonds.
c. A six carbon member ring containing three alternation
double bonds.
d. A hydrocarbon that has a pleasant aromatic odor.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 67

 Section 13.13

Aromatic Hydrocarbons

An aromatic hydrocarbon consists of:

a. A six carbon member ring containing one or more
double bonds.
b. A six carbon member ring containing two or more
double bonds.
c. A six carbon member ring containing three alternation
double bonds.
d. A hydrocarbon that has a pleasant aromatic odor.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 68

 Section 13.14

Nomenclature for Aromatic Hydrocarbons

Naming Benzene Derivatives

• Name of the substituent is used as a prefix to the name
benzene
• Numbers or non-numerical prefixes are used in the
presence of more than one substituent
– Ortho - 1,2 disubstitution
– Meta - 1,3 disubstitution
– Para - 1,4 disubstitution

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 69

 Section 13.14

Nomenclature for Aromatic Hydrocarbons

Two substituents separated by one carbon on the

simplest aromatic hydrocarbon benzene are said
to be _____ to each other.
a. Ortho
b. Meta
c. Para
d. Next

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 70

 Section 13.14

Nomenclature for Aromatic Hydrocarbons

Two substituents separated by one carbon on the

simplest aromatic hydrocarbon benzene are said
to be _____ to each other.
a. Ortho
b. Meta
c. Para
d. Next

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 71

 Section 13.15

Properties of and Sources for Aromatic Hydrocarbons

• Insoluble in water
• Soluble in non-polar solvents
• Less dense than water
• Benzene is a colorless, flammable liquid that burns with
sooty flame
• Petroleum is the primary source of aromatic
hydrocarbons

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 72

 Section 13.15

Properties of and Sources for Aromatic Hydrocarbons

The density of aromatic hydrocarbons with respect

to water is:
a. The same as the density of water.
b. Less dense than water.
c. More dense than water.
d. The densities cannot be compared.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 73

 Section 13.15

Properties of and Sources for Aromatic Hydrocarbons

The density of aromatic hydrocarbons with respect

to water is:
a. The same as the density of water.
b. Less dense than water.
c. More dense than water.
d. The densities cannot be compared.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 74

 Section 13.15

Properties of and Sources for Aromatic Hydrocarbons

Chemical Reactions of Aromatic Hydrocarbons

• Aromatic hydrocarbons do not readily undergo the
addition reactions characteristic of other unsaturated
hydrocarbons
• Benzene undergoes substitution reactions
• Important substitution reactions
– Alkylation

AlCl
CH –CH
2 3
+ CH –CH –Cl
3 + HCl
3 2

Benzene Chloroethane Ethylbenzene

– Halogenation
Br
FeBr
+ Br 3
+ HBr
2
Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 75

 Section 13.15

Properties of and Sources for Aromatic Hydrocarbons

Aromatic hydrocarbons undergo two types of

_____ reactions known as _____ and _____.
a. Addition; alkylation; hydrohalogenation
b. Addition; alkylation; halogenation
c. Substitution; alkylation; hydrohalogenation
d. Substitution; alkylation; halogenation

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 76

 Section 13.15

Properties of and Sources for Aromatic Hydrocarbons

Aromatic hydrocarbons undergo two types of

_____ reactions known as _____ and _____.
a. Addition; alkylation; hydrohalogenation
b. Addition; alkylation; halogenation
c. Substitution; alkylation; hydrohalogenation
d. Substitution; alkylation; halogenation

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 77

 Section 13.16

Fused-Ring Aromatic Hydrocarbons

• Fused-ring aromatic hydrocarbons: Aromatic

hydrocarbons whose structures contain two or more
rings fused together
• Examples

Anthracene Phenanthracene
Naphthalene

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 78

 Section 13.16

Fused-Ring Aromatic Hydrocarbons

Naphthalene, anthracene, and phenanthrene are

examples of _____ aromatic hydrocarbons.
a. Two-ring
b. Multiple-ring
c. Fused-ring
d. Substituted

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 79

 Section 13.16

Fused-Ring Aromatic Hydrocarbons

Naphthalene, anthracene, and phenanthrene are

examples of _____ aromatic hydrocarbons.
a. Two-ring
b. Multiple-ring
c. Fused-ring
d. Substituted

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 80

 Chapter 13

The IUPAC name of the following alkene is:

a. cis-4-heptane.
b. trans-4-heptene.
c. cis-3-heptene.
d. trans-3-heptene.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 81

 Chapter 13

The IUPAC name of the following alkene is:

a. cis-4-heptene.
b. trans-4-heptene.
c. cis-3-heptene.
d. trans-3-heptene.

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 82

 Chapter 13

What is the correct IUPAC name of the following

aromatic compound?

a.1,3-dichloro-4-ethyl-2-methylbenzene
b.1,5-dichloro-4-ethyl-6-methylbenzene
c.2,6-dichloro-3-ethyltoluene
d.2,6-dichloro-5-ethyltoluene
Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 83

 Chapter 13

What is the correct IUPAC name of the following

aromatic compound?

a.1,3-dichloro-4-ethyl-2-methylbenzene
b.1,5-dichloro-4-ethyl-6-methylbenzene
c.2,6-dichloro-3-ethyltoluene
d.2,6-dichloro-5-ethyltoluene
Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 84