SECTION 2

Main Ideas
Alkanes contain only single
Hydrocarbons
bonds.
Key Terms
Cycloalkanes have a ringed saturated hydrocarbon natural gas alkyne
structure. alkane petroleum aromatic hydrocarbon
cycloalkane unsaturated hydrocarbon benzene
Organic compounds have alkyl group alkene
systematic names.

The properties of alkanes are Hydrocarbons are compounds that contain only carbon and hydrogen. They make
related to the lengths of their up the simplest class of organic compounds. All other organic compounds can be
viewed as hydrocarbons in which one or more hydrogen atoms have been replaced
carbon chains.
by other atoms or groups of atoms.
Unsaturated hydrocarbons have Hydrocarbons are grouped mainly by the type of bonding between carbon
at least one carbon-carbon atoms. Saturated hydrocarbons are hydrocarbons in which each carbon atom
in the molecule forms four single covalent bonds with other atoms.
double bond.

MAIN IDEA
Alkanes contain only single bonds.
Hydrocarbons that contain only single bonds are alkanes. In Figure 2.1, the
molecular formulas, structural formulas, and space-filling models are
given for alkanes with one to four carbon atoms. If you examine the
molecular formulas for successive alkanes in Figure 2.1, you will see a
clear pattern. Each member of the series differs from the preceding one
by one carbon atom and two hydrogen atoms. For example, propane,
C3H8, differs from ethane, C2H6, by one carbon atom and two hydrogen
atoms, a — CH2 — group.
H
    H H
   H  H
         
H- C  - C  -H H- C
 - C
 - C
  -H

     
      
H H H H H
ethane propane
Compounds that differ in this fashion belong to a homologous series.
A homologous series is one in which adjacent members differ by a
constant unit. It is not necessary to remember the molecular formulas for
all members of a homologous series. Instead, a general molecular for-
mula can be used to determine the formulas. Look at the molecular
formulas for ethane and propane, C2H6 and C3H8. They both fit the
formula CnH2n+2. For ethane, n = 2, so there are two carbon atoms and
(2 × 2) + 2 = 6 hydrogen atoms. For propane, n = 3, so there are three
carbon atoms and (2 × 3) + 2 = 8 hydrogen atoms. Now consider a
molecule for which we do not know the molecular formula. Suppose a
member of this series has 30 carbon atoms in its molecules. Then n = 30,
and there are (2 × 30) + 2 = 62 hydrogen atoms. The formula is C30H62.
Incidentally, an alkane with this formula, known as squalane, does exist
and is a component in some moisturizers.

682 Chapter 22
FIGURE 2.1

ALKANES WITH ONE TO FOUR CARBON ATOMS

Molecular formulas Structural formulas Space-filling models

H

CH4 H- C -H

H
methane

H H
 
C2H6 H- C - C -H
 
H H
ethane

H H H
  
C3H8 H- C - C - C -H
  
H H H
propane

H H H H
   
H- C - C - C - C -H
   
H H H H
C4H10 butane

H H H
| | |
H- C ——— C ——— C - H
| | |
H H –– C –– H H
|
H
2-methylpropane

Notice that for alkanes with three or fewer carbon atoms, only one
molecular structure is possible. However, in alkanes with more than three
carbon atoms, the chains can be straight or branched. Thus, alkanes with
four or more carbon atoms have structural isomers. There are two pos-
sible structural isomers for alkanes with four carbon atoms, butane and
2-methylpropane.
The number of structural isomers increases greatly as the number of
carbon atoms in alkanes increases. There are three isomeric C5H12
alkanes, five isomeric C6H14 alkanes, and nine isomeric C7H16 alkanes.
There are nearly 37 million possible isomers of C25H52, although most
have never been prepared or isolated.

Organic Chemistry 683

 MAIN IDEA
Cycloalkanes have a ringed structure.
Cycloalkanes are alkanes in which the carbon atoms are arranged in a ring, or
cyclic, structure. The structural formulas for cycloalkanes are often drawn
in a simplified form. In these skeletal representations, such as the one
below on the right, it is understood that there is a carbon atom at each
corner and enough hydrogen atoms to complete the four bonds to each
carbon atom.

CH2
      
CH2 CH2 or
      
CH2—CH2
cyclopentane cyclopentane
CHECK FOR UNDERSTANDING The general structure for cycloalkanes, CnH 2n, shows that they have
Infer Even though they don’t follow 2 × n hydrogen atoms, two fewer hydrogen atoms than noncyclic al-
the general formula Cn H2n + 2, why kanes, CnH 2n+2, have. This is because cycloalkanes have no free ends
are cycloalkanes still alkanes? where a carbon atom is attached to three hydrogen atoms. Another
example, of a four-carbon alkane and cycloalkane, is shown below.
H
  H 
H  
  H  H  H    
        H- C
 -C
        -H
 - C
H- C  -C -C -H 
     
       
         H- C
  -C
  -H
FIGURE 2.2 H H H H    
H H
CARBON-ATOM CHAIN
butane cyclobutane
PREFIXES
C4H10 C4H8
Number of
carbon atoms Prefix
MAIN IDEA
1 meth- Organic compounds have systematic names.
2 eth- Historically, the names of many organic compounds were derived
from the sources in which they were found. As more organic compounds
3 prop- were discovered, a systematic naming method became necessary.
The systematic method used primarily in this book was developed by the
4 but- International Union of Pure and Applied Chemistry, IUPAC.
5 pent-
Unbranched-Chain Alkane Nomenclature
6 hex-
To name an unbranched alkane, find the prefix in Figure 2.2 that corre-
7 hept- sponds to the number of carbon atoms in the chain of the hydrocarbon.
Then add the suffix -ane to the prefix. An example is shown below.
8 oct- 1 2 3 4 5 6 7
CH3- CH2- CH2- CH2- CH2- CH2- CH3

9 non- heptane

10 dec- The molecule has a chain seven carbon atoms long, so the prefix hept- is
added to the suffix -ane to form heptane.

684 Chapter 22
FIGURE 2.3

SOME STRAIGHT-CHAIN ALKYL GROUPS

Alkane Name Alkyl group Name

CH4 methane -CH3 methyl

CH3-CH3 ethane -CH2-CH3 ethyl

CH3-CH2-CH3 propane -CH2-CH2-CH3 propyl

CH3-CH2-CH2-CH3 butane -CH2-CH2-CH2-CH3 butyl

CH3-CH2-CH2-CH2-CH3 pentane -CH2-CH2-CH2-CH2-CH3 pentyl

Branched-Chain Alkane Nomenclature

The naming of branched-chain alkanes also follows a systematic method.
The hydrocarbon branches of alkanes are alkyl groups. Alkyl groups are
groups of atoms that are formed when one hydrogen atom is removed from an
alkane molecule. Alkyl groups are named by replacing the suffix -ane of
the parent alkane with the suffix -yl. Some examples of alkyl groups are
shown in Figure 2.3. Alkyl group names are used when naming branched-
chain alkanes. We will present only the method for naming simple
branched-chain alkanes with only straight-chain alkyl groups. Consider
the following molecule.
CH3 CH3
CH3 — CH — CH — CH — CH — CH — CH — CH
2 2 2 3
CH — CH3
CH3

To name this molecule, locate the parent hydrocarbon. The parent

hydrocarbon is the longest continuous chain that contains the most
straight-chain branches. In this molecule, there are two chains that are
eight carbon atoms long. The parent hydrocarbon is the chain that
contains the most straight-chain branches. Do not be tricked by the
way the molecule is drawn. The longest chain may be shown bent.

CH3 CH3
CH3 — CH2 — CH2 — CH — CH — CH — CH2— CH3
CH — CH3
CH3

NOT

CH3 CH3
CH3— CH2— CH2— CH — CH — CH — CH2 — CH3
CH — CH3
CH3

Organic Chemistry 685

 To name the parent hydrocarbon, add the suffix -ane to the prefix oct- (for
a carbon-atom chain with eight carbon atoms) to form octane. Now
identify and name the alkyl groups.

CH3 CH3
CH3 — CH2— CH2— CH — CH — CH — CH2— CH3
CH — CH3
CH3

The three —CH3 groups are methyl groups. The —CH2—CH3 group is an
ethyl group. Arrange the names in alphabetical order in front of the name
of the parent hydrocarbon.
ethyl methyloctane
To show that there are three methyl groups present, attach the prefix tri-
to the name methyl to form trimethyl.
ethyl trimethyloctane
Now, we need to show the locations of the alkyl groups on the parent
hydrocarbon. Number the octane chain so that the alkyl groups have the
lowest numbers possible.
CH3 CH3
8 7 6 5 4 3
CH3 CH2
— — CH —
2 CH — CH — CH — CH2 — CH3
2CH — CH3

1CH3

NOT
Petroleum Engineer
CH3 CH3
Petroleum engineers search for 1 2 3 4 5 6
underground reservoirs of oil or CH3 — CH2— CH2— CH — CH — CH — CH2 — CH3
natural gas. They then work with 7CH — CH3
other scientists and engineers to 8CH3
develop and oversee drilling and
production operations. Petroleum Place the location number of each of the alkyl groups in front of its name.
engineers are also responsible for Separate the numbers from the names of the alkyl groups with hyphens.
developing technology and methods
The ethyl group is on carbon 3.
to increase the amount of oil or gas
obtained and to lower the cost of 3-ethyl trimethyloctane
drilling and production operations. In Because there are three methyl groups, there will be three numbers,
addition to possessing a broad range
separated by commas, in front of trimethyl.
of engineering expertise (chemical,
mechanical, or electrical), a petroleum 3-ethyl-2,4,5-trimethyloctane
engineer must also apply the basic The full name is 3-ethyl-2,4,5-trimethyloctane.
sciences of chemistry, geology,
physics, and mathematics. The procedure for naming simple branched-chain alkanes can be
summarized as shown in the list on the next page.

686 Chapter 22
Alkane Nomenclature

1. Name the parent hydrocarbon. Find the longest continuous chain of

carbon atoms that have straight-chain branches. Add the suffix -ane to
the prefix corresponding to the number of carbon atoms in the chain.
2. Add the names of the alkyl groups. Add the names of the alkyl
groups in front of the name of the parent hydrocarbon in alphabeti-
cal order. When there is more than one branch of the same alkyl
group present, attach the appropriate numerical prefix to the name:
di = 2, tri = 3, tetra = 4, and so on. Do so after the names have been
put in alphabetical order.
3. Number the carbon atoms in the parent hydrocarbon. If one or
more alkyl groups are present, number the carbon atoms in the
continuous chain to give the lowest numbers possible in the name.
If there are two equivalent lowest positions with two different alkyl
groups, give the lowest number to the alkyl group that comes first in
the name. (This will be the alkyl group that is first in alphabetical
order, before any prefixes are attached.)
4. Insert position numbers. Put the position numbers of each alkyl
group in front of the name of that alkyl group.
5. Punctuate the name. Use hyphens to separate the position numbers
from the names. If there is more than one number in front of a name,
use commas to separate the numbers.

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Sample Problem A Name the following simple branched-chain Solve It! Cards
alkane: HMHScience.com
CH3–– CH –– CH2–– CH –– CH –– CH3
|     |     |    
CH3 CH3 CH3

SOLVE 1. Identify and name the parent hydrocarbon.

CH3–– CH –– CH2–– CH –– CH –– CH3
|     |     |    
CH3 CH3 CH3
Because the longest continuous chain contains six carbon atoms, the parent
hydrocarbon is hexane.
2. Identify and name the alkyl groups attached to the chain.
CH3–– CH –– CH2–– CH –– CH –– CH3
|     |     |    
CH3 CH3 CH3
There is only one type of alkyl group, with one carbon atom. Alkyl groups
with one carbon atom are methyl groups. Add the name methyl in front of
the name of the continuous chain. Add the prefix tri- to show that there are
three methyl groups present.
trimethylhexane

Continued Organic Chemistry 687

 Naming Alkanes (continued)

3. Number the carbon atoms in the continuous chain so that the

alkyl groups have the lowest numbers possible.
6 5 4 3 2 1
CH3CH  CH2  CH  CH CH3
CH3 CH3 CH3
4. The methyl groups are on the carbon atoms numbered 2, 3,
and 5. Put the numbers of the positions of the alkyl groups,
separated by commas, in front of the name of the alkyl group.
Separate the numbers from the name with a hyphen.
2,3,5-trimethylhexane

Answers in Appendix E
Name the following molecules:
  
1. CH3––  
CH–– CH2–– CH3
|    
  
CH
  3 CH3
2. CH3 CH2 CH  CH  CH2  CH3
CH2
CH3

MAIN IDEA
The properties of alkanes are related to the lengths
of their carbon chains.
Properties for some straight-chain alkanes are listed in Figure 2.4. The
trends in these properties can be explained by examining the structure of
alkanes. The carbon-hydrogen bonds of alkanes are nonpolar. The only
forces of attraction between nonpolar molecules are weak intermolecular
forces, or London dispersion forces. The strength of London dispersion
forces increases as the mass of a molecule increases.
FIGURE 2.4

PROPERTIES OF STRAIGHT-CHAIN ALKANES

Molecular State at room
formula IUPAC name Boiling point (°C) temperature

CH4 methane -164 gas

C2H6 ethane -88.6
C3H8 propane -42.1
C4H10 butane -0.5
C5H12 pentane 36.1 liquid
C8H18 octane 125.7
C10H22 decane 174.1
C17H36 heptadecane 301.8 solid
C20H42 eicosane 343.

688 Chapter 22
 Physical States FIGURE 2.5
The physical states at which some alkanes exist at room temperature and
Solid Alkanes Paraffin wax, used
atmospheric pressure are found in Figure 2.4. Alkanes that have the lowest
in candles, contains solid alkanes.
molecular mass—those with one to four carbon atoms—are gases. Molecules of paraffin wax contain 26
Natural gas is a fossil fuel composed primarily of alkanes containing one to to 30 carbon atoms.
four carbon atoms. These alkanes are gases because they are very small
molecules. Therefore, they have weak London dispersion forces between
them and are not held together tightly. Larger alkanes are liquids.
Gasoline and kerosene consist mostly of liquid alkanes. Stronger London
dispersion forces hold these molecules close enough together to form
liquids. Alkanes that have a very high molecular mass are solids, corre-
sponding to a greater increase in London dispersion forces. Paraffin wax
contains solid alkanes. It can be used in candles, as shown in Figure 2.5.

Boiling Points
The boiling points of alkanes, also shown in Figure 2.4, increase with
molecular mass. As London dispersion forces increase, more energy is
required to pull the molecules apart. This property is used in the separation
of petroleum, a major source of alkanes. Petroleum is a complex mixture of
different hydrocarbons that varies greatly in composition. The hydrocarbon
FIGURE 2.7
molecules in petroleum contain from 1 to more than 50 carbon atoms. This
range allows the separation of petroleum into different portions that have Fractional Distillation
different boiling-point ranges, as shown in Figure 2.6. In fractional distilla- Fractional distillation takes place in
tion, components of a mixture are separated on the basis of boiling point, petroleum refinery towers.
by condensation of vapor in a fractionating column. Figure 2.7 shows an
example of refinery towers in which the process takes place. During its
fractional distillation, petroleum is heated to about 370°C. Nearly all
components of the petroleum are vaporized at this temperature. As the
vapors rise in the fractionating column, or tower, they are gradually cooled.
Alkanes that have higher boiling points have higher condensation
temperatures and condense for collection lower in the tower. For example,
lubricating oils, which have higher condensation temperatures than
gasoline has, are collected lower in the fractionating tower.

FIGURE 2.6

PETROLEUM FRACTIONS
Size range of Boiling-point
Fraction molecules range (°C)
(tr) ©David Spindel/SuperStock; (br) ©Mike Dobel/Alamy

Gasoline C4–C12 up to 200

Kerosene C10–C14 180–290
Middle distillate, such as heating oil, C12–C20 185–345
gas-turbine fuel, diesel
Wide-cut gas oil, such as C20–C36 345–540
lubricating oil, waxes

Asphalt above C36 residues

Organic Chemistry 689

 MAIN IDEA
Unsaturated hydrocarbons have at least one carbon-
carbon double bond.
Hydrocarbons that do not contain the maximum amount of hydrogen are
referred to as unsaturated. Unsaturated hydrocarbons are hydrocarbons in
which not all carbon atoms have four single covalent bonds. An unsaturated
hydrocarbon has one or more double bonds or triple bonds. Carbon atoms
can easily form double and triple bonds to other carbon atoms, so multiple
bonds between carbon atoms are common in organic compounds.

Alkenes
Alkenes are hydrocarbons that contain double covalent bonds. Some exam-
ples of alkenes are given in Figure 2.8. Notice that because alkenes have a
double bond, the simplest alkene, ethene, has two carbon atoms.
Carbon atoms linked by double bonds cannot bind as many atoms as
those that are linked by only single bonds. An alkene with one double
bond has two fewer hydrogen atoms than the corresponding alkane.
H H H H
   
H- C - C - C -H H- C = C - C -H
     
H H H H H H
C3H8 C3H6
Thus, the general formula for noncyclic alkenes with one double bond
is CnH2n.
Because alkenes have a double bond, they can have geometric isomers,
as shown in the examples below.
CHECK FOR UNDERSTANDING H H H CH3
Identify Is the compound C10H20    C = C       C = C   
an alkane or an alkene? Can you
know for sure? CH3 CH3 CH3 H

cis-2-butene trans-2-butene

FIGURE 2.8

STRUCTURES OF ALKENES
ethene propene trans-2-butene cis-2-butene

H H H H H CH3 H H
Structural C=C C=C C=C C=C
formula
H H CH3 H CH3 H CH3 CH3

Ball-and-stick
model

690 Chapter 22
MC99 PE C20 000 023bA
MC99 PE C20 000 023bA
Systematic Names of Alkenes
The rules for naming a simple alkene are similar to those for naming an
alkane. The parent hydrocarbon is the longest continuous chain of Carbon Allotropes
carbon atoms that contains the double bond. Elemental carbon occurs in several
CH2 CH3 CH 2 CH 3 forms, called allotropes, which have
NOT
CH2 
 C  CH2 CH 2 CH3 CH2 
 C  CH 2 CH 2 CH 3 very different properties. Diamond
is a colorless, crystalline solid form
pentene hexene
of carbon, in which each atom is
The carbon atoms in the chain are numbered so that the first carbon tetrahedrally bonded to four others
atom in the double bond has the lowest number. in a network. This three-dimensional
CH 2  CH 3 bonding makes diamond an insulator
1 2 3 4 5 and the hardest material known.
CH2 
 C  CH 2CH 2 CH 3
Graphite is a soft, black, crystalline
1-pentene form of carbon that is a fair conductor
The position number and name of the alkyl group are placed in front of electricity. The carbon atoms in
of the double-bond position number. This alkyl group has two carbon graphite are bonded together in
atoms, an ethyl group. It is on the second carbon atom of the parent layers. Within each layer, each atom is
hydrocarbon. bonded to three other carbon atoms.
But because adjacent layers are held
2-ethyl-1-pentene together only by very weak London
If there is more than one double bond, the suffix is modified to indicate dispersion forces, graphite is very soft.
the number of double bonds: 2 = -adiene, 3 = -atriene, and so on. Diamond and graphite have been
known for thousands of years. In the
CH2=CH-CH2-CH=CH2 mid-1980s, a new solid allotropic
1,4-pentadiene form of carbon known as a fullerene,
or, informally, “buckyball,” was
The procedure for naming alkenes can be summarized as follows. discovered in the soot that forms
when carbon-containing materials
are burned with limited oxygen. The
Alkene Nomenclature structure of a fullerene consists of a
Use the rules for alkane nomenclature listed earlier in this section, near-spherical cage of carbon atoms.
with the following exceptions. The most stable fullerene is C60, the
structure of which resembles the
1. Name the parent hydrocarbon. Locate the longest continuous design of a soccer ball.
chain that contains the double bond(s). If there is only one double
bond, add the suffix -ene to the prefix corresponding to the number
of carbon atoms in this chain. If there is more than one double bond,
modify the suffix to indicate the number of double bonds. For
example, 2 = -adiene, 3 = -atriene, and so on.
2. Add the names of the alkyl groups.
3. Number the carbon atoms in the parent hydrocarbon. Number the
carbon atoms in the chain so that the first carbon atom in the double
bond nearest the end of the chain has the lowest number. If number-
ing from both ends gives equivalent positions for two double bonds,
then number from the end nearest the first alkyl group.
4. Insert position numbers. Place double-bond position numbers
immediately before the name of the parent hydrocarbon alkene.
Place alkyl group position numbers immediately before the name
of the corresponding alkyl group.
5. Punctuate the name.

Organic Chemistry 691

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Sample Problem B Name the following alkene.
CH 3
CH3 CH  C  CH2


CH2 CH3

ANALYZE 1. Identify and name the parent hydrocarbon.

CH3
CH3 CH C  CH2
CH2  CH3

The parent hydrocarbon has four carbon atoms and one double bond, so it is
named butene.
2. Identify and name the alkyl groups.
CH 3
CH3 CH  C  CH 2
CH 2 CH 3

The alkyl groups are ethyl and methyl.

Place their names in front of the name of the parent hydrocarbon in alpha-
betical order.
ethyl methyl butene
3. Number the carbon chain to give the double bond the lowest position.

CH 3
4 3 2 1
CH3 CH  C  CH 2
CH 2 CH 3

SOLVE Place the position number of the double bond in front of butene. Place the
position numbers of the alkyl groups in front of each alkyl group. Separate the
numbers from the name with hyphens. The full name is
2-ethyl-3-methyl-1-butene.

Answers in Appendix E

Name the following alkenes:

1. CH3-CH2-CH2-CH=CH-CH3 CH3

CH CH3
CH3
 

4. CH3- C -CH3-CH = C - CH3
2. CH3-CH= CH-CH3
CH3

3. CH3- CH -CH=CH-CH2-CH3

692 Chapter 22
 FIGURE 2.9

Alkenes in Nature α-farnesene is a solid alkene found in the natural wax covering of apples.
Can you determine the IUPAC name for this large alkene?

CH3 CH CH2 CH CH CH

C CH2 C CH2 C CH2

CH3 CH3 CH3

α-farnesene

Properties and Uses of Alkenes

Alkenes are nonpolar and show trends in properties similar to those of
alkanes in boiling points and physical states. For example, α-farnesene FIGURE 2.10
has 15 carbon atoms and 4 double bonds, as shown in Figure 2.9. This
Fruit Ripening Ethene is a plant
large alkene is a solid at room temperature and atmospheric pressure. −
CHhormone
3 CH3 that triggers fruit ripening. At
It is found in the natural wax covering of apples. Ethene, the smallest
ordinary conditions, ethene is a gas.
alkene, is a gas. Ethene is commonly called ethylene.
Ethene is the hydrocarbon commercially produced in the greatest
quantity in the United States. It is used in the synthesis of many plastics
and commercially important alcohols. Ethene is also an important plant
hormone. Induction of flowering and the ripening of fruit, as shown in
Figure 2.10, are effects of ethene hormone action that can be manipulated
by commercial growers.

Alkynes
Hydrocarbons with triple covalent bonds are alkynes. Like the double bond of
alkenes, the triple bond of alkynes requires that the simplest alkyne have
two carbon atoms.
H-C≡C-H H H
ethyne C=C
H H
The general formula for the alkynes is CnH2n–2. Alkynes have four
fewer hydrogen atoms than the corresponding alkanes and two fewer
hydrogen atoms than the corresponding alkenes. The simplest alkyne is
ethyne, more commonly known as acetylene.

H H H H
 
H- C - C -H   C=C   H-C≡C-H
 
H H H H
C2H6 C2H4 C2H2
ethane ethene ethyne

Organic Chemistry 693

 Systematic Naming of Alkynes
Alkyne nomenclature is almost the same as alkene nomenclature. The
only difference is that the -ene suffix of the corresponding alkene is
replaced with -yne. A complete list of rules follows.

Alkyne Nomenclature
Use the rules for alkane nomenclature listed earlier in this section,
with the following exceptions.
1. Name the parent hydrocarbon. Locate the longest continuous chain
that contains the triple bond(s). If there is only one triple bond, add
the suffix -yne. If there is more than one triple bond, modify the suffix.
For example, 2 = –adiyne, 3 = –atriyne, and so on.
2. Add the names of the alkyl groups.
3. Number the carbon atoms in the parent hydrocarbon. Number
the carbon atoms in the chain so that the first carbon atom in the
triple bond nearest the end of the chain has the lowest number.
4. Insert position numbers. Place the position numbers of the triple
bond immediately before the name of the parent hydrocarbon
alkyne. Place alkyl group position numbers immediately before
the name of the corresponding alkyl group.
5. Punctuate the name.

Two examples of correctly named alkynes are given below.

CH3-CH2-CH2-C≡CH CH≡C- CH -CH3
|
CH3
1-pentyne 3-methyl-1-butyne

Properties and Uses of Alkynes

Alkynes are nonpolar and exhibit the same trends in boiling points and
physical states as other hydrocarbons. The smallest alkyne, ethyne, is a
gas. The combustion of ethyne when it is mixed with pure oxygen pro-
duces the intense heat of welding torches, as shown in Figure 2.11. As
mentioned, the common name of ethyne is acetylene, so these welding
torches are commonly called oxyacetylene torches.
FIGURE 2.11

Alkynes Ethyne is the fuel used in

oxyacetylene torches. Oxyacetylene
torches can reach temperatures of
over 3000°C.
(br) ©Kevin Anderson/Getty Images

694 Chapter 22
Aromatic Hydrocarbons FIGURE 2.12
Aromatic hydrocarbons are hydrocarbons that have six-membered carbon
Aromatic Hydrocarbons
rings and delocalized electrons. Benzene is the primary aromatic hydrocarbon.
Electron orbitals in benzene overlap to
The molecular formula of benzene is C6H6. One possible structural
form continuous p -orbitals that allow
formula is a six-carbon-atom ring with three double bonds.
the delocalized electrons to spread
H uniformly over the entire ring.
H H
H H

H H H H
H
H H
However, benzene does not behave chemically like an alkene. The
entire molecule lies in the same plane, as shown in Figure 2.12. Benzene
contains six equivalent C–C bonds, and the structure of the benzene ring
allows electrons to be spread through delocalized p-orbitals over the
whole ring. The structural and skeletal formulas below show benzene as
a resonance hybrid, representing the delocalization of electrons.
H
H H

H H
H

Aromatic hydrocarbons can be thought of as derivatives of benzene. The CHECK FOR UNDERSTANDING
simplest have one benzene ring, as shown in the following example. Defend How does the circle in the
CH3 middle of the benzene ring better
represent the type of bonding in
benzene?

methylbenzene

SECTION 2 FORMATIVE ASSESSMENT

Reviewing Main Ideas 5. Name the following compounds:
a. CH3- CH2- CH3
1. List the basic structural features that

characterize each of the following hydrocarbons:
CH3 - CH- CH- CH2- CH3
a. alkanes
b. alkenes b. CH2=CH-CH=CH2
c. alkynes c. CH3-C≡C-CH2-CH3
d. aromatic hydrocarbons
Critical Thinking
2. Draw all of the condensed structural formulas
that can represent C5H12. 6. ANALYZING INFORMATION Write the
structural formulas for an alkane, an alkene,
3. Give the systematic name for each compound in and an alkyne that have five carbon atoms each.
your answers to item 2. Why are these three hydrocarbons not consid-
4. Give examples of a property or use of three ered isomers?
hydrocarbons.

Organic Chemistry 695