NAME PER DATE D U E _

ACTIVE LEARNING IN CHEMISTRY EDUCATION

CHAPTER25
INTRODUCTION
TO ORGANIC
COMPOUNDS
(Part 1)

25-1 ©1997, A.J. Girondi

SECTION 25.1 Introduction to Carbon Compounds

All substances can be classified as being either organic or inorganic. So far, our study of
chemistry has dealt mainly with inorganic compounds. Originally, organic substances were considered to
be those carbon compounds that were extracted from living things, while inorganic ones were
compounds that did not originate in living systems. An organic compound is defined as a substance that
contains the element carbon. However, some compounds that contain carbon are considered to be
inorganic. A better definition may be that organic compounds have a carbon base, that carbon is the
"backbone" of the compounds.

Organic chemistry plays a very important role in our daily lives. Many of the clothes we wear are
made of rayon, dacron, nylon and orion. These are all synthetic (man-made) organic compounds. Plastics
of all sorts are synthetic organic compounds, too. Petroleum is a naturally occurring organic substance,
but synthetic rubber and plastics are two of the by-products of petroleum.

A large number of modern chemical materials have been developed fro,m by-products of
petroleum. In addition to these items, other materials such as sulfa drugs, penicillin, cortisone, perfumes,
detergents, vitamins, pesticides, anesthetics, and many of the more modern antibiotics are among the
contributions made to society through a study of organic chemistry.

Throughout the 18th century, early chemists unsuccessfully tried to synthesize organic
substances, starting with inorganic materials in their laboratories. Their failures gave rise to the "vital force
theory" which stated that organic compounds could only be produced by a "vital force" which was
responsible for life itself. This conclusion was closely tied to religious beliefs at the time. However, in
1828, the German chemist, Friedrich Wohler, succeeded in synthesizing an organic compound known as
urea, starting with two inorganic compounds. Thereafter, many other organic compounds were
synthesized in the same way in laboratories around the world. By 1850, the "vital force theory" was
discredited. From that time on, organic and inorganic chemistry were recognized as two major fields of the
science. There are over 90,000 known inorganic compounds. However, there are well over one million
known organic compounds, and many more are being synthesized by chemists every year!

Why are there so many organic compounds? Well, carbon atoms can attach themselves to each
other in wide variety of ways. They can join together to form short or long chains, and they can form rings
of many kinds, as well:

C-C-C cI
c
I
cI c c-c
I
c /\ I I
C-C-C-C-C-C C-C-C-C-C c-c c-c
Carbon Chains Carbon Rings

The chains and rings can have branches and cross-links with atoms of other elements (mainly hydrogen)
attached to the carbon atoms. Different arrangements of carbon atoms correspond to different
compounds, and each compound has its own characteristic properties.

We are going to approach the subject of organic chemistry in terms of organic nomenclature.
Nomenclature involves the naming of compounds. We will restrict ourselves to the simpler organic
compounds, because the more complex ones can get really complicated. You will be given a set of rules
to follow as you name compounds. These rules must be followed very carefully. Success in learning
organic nomenclature will involve some memorization on your part, but it will rely mainly on a logical
approach to the problems presented.

The second most abundant element found in organic compounds is hydrogen. This chapter will
deal exclusively with compounds composed of only carbon and hydrogen. These are called

25-3 ©1997, A.J. Girondi

hydrocarbons. These two elements can combine in countless ways. The structures of some
hydrocarbons are shown below. The lines between the atomic symbols represent bonds. There are
three types of carbon to carbon bonds:

H H H H
I I
H-C-C-H ' c=c /
H-c=c-H
I I
H/ 'H
H H
single bond double bond triple bond

In each case you will note that carbon has a total of four bonds. This is because carbon ~----~
has four valence electrons. There are only a few carbon compounds in which carbon
does not have four bonds. One example is carbon monoxide. In this chapter,
however, we will deal only with organic compounds in which the carbon atoms have
- .
.·c=o·
carbon
four bonds. After we have studied the hydrocarbons, Chapters 26 and 27 will monoxide
introduce you to the names and structures of organic compounds which contain other ....___ _ _ ____.
elements in addition to carbon and hydrogen.

Section 25.2 The Alkanes

The alkane family represents the simplest of the hydrocarbons. The general formula for the
compounds in this family is CnH2n+2, where "n" equals the number of carbon atoms in the molecule. For
example, if you substitute a 1 into this formula you will get CH4. Substitute a 2 and you will get C2H5.
These are the first two members of the family. The compounds in the alkane family are often called
saturated compounds, which means that the molecules contain only single bonds between the carbon
atoms.

Naming alkanes is fairly simple. The prefix in the name of each compound indicates the number of
carbon atoms present. All alkanes have a suffix of -ane. A list of alkane prefixes is shown in Problem 1
which has been partially completed for you. To make writing formulas or drawing structures easier, the
hydrogens on the carbons are not always shown (note the structures on page 25-3); however, you should
assume that enough hydrogen atoms are present to give each carbon atom 4 bonds.

Problem 1. Give the name and molecular formula for each compound below. Use the formula CnH2n+2
to determine the formula, and add the suffix "ane" to the prefixes to obtain the names.

Prefix No. of Carbons Name Molecular Formula

a. meth- methane CH4

b. eth- 2 ethane C2H6

c. prop- 3 propane C3Hs

d. but- 4 butane C4H10

e. pent- 5 ~entane C5H12
f. hex- 6 hexane C6H14
g. he pt- 7 heptane C7H16
254 ©1997, A.J. Girondi
h. oct- 8 octane C8H18
i. non- 9 nonane C9H20
j. dee- 10 decane

In problem 1, you were writing molecularformulas. The kinds of formulas seen at the top of page
25-4 are known as structural formulas. Writing structural formulas for organic compounds can become very
cumbersome when all of the chemical bonds are included in the drawings. To remedy this problem,
chemists have developed a shorthand method of writing structural formulas that involves condensing the
structures. In this shorthand method, the carbon atoms are still written separately (separated by hyphens),
but the hydrogens which are bound to carbons are not. Instead, the hydrogens are written to the right of
the carbon atoms to which they are bonded. This method of representing organic compounds is known
as the condensed structural formula. Study the examples of condensed structural formulas below.

Compound Molecular Formula Structural Formula Condensed Structural Formula

H
methane I
H-C-H
I
H

HHHH
I I I I
butane H-C-C-C-C-H
I I I I
HHHH

Problem 2. Complete the exercise below.

Compound Name Molecular Formula Condensed Structural Formula

a. methane _ _ _CH4 CH4_ _ _ _ _,

b. ethane C2H6 CH3CH3

c. propane C3H8 CH3CH2CH3
d. butane

e. pentane C5H12 CH3CH2CH2CH2CH3

f. hexane C614 CH3CH2CH2CH2CH2CH3
g. heptane C7H16 CH3CH2CH2CH2CH2CH2CH3
h. octane C8H18 CH3CH2CH2CH2CH2CH2CH2CH3
i. nonane C9H20 CH3CH2CH2CH2CH2CH2CH2CH2CH3
j. decane C10H22 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3

25-5 ©1997, A.J. Girondi

Section 25.3 Alkyl Groups

Carbon chains are not rigid structures. They can bend and flex freely. When we say that an alkane
has a "straight" chain, we don't really mean straight. We mean that it is a continuous chain, rather than a
branched chain. The two structures below both contain six carbon atoms. The one on the left is
"straight," while the one on the right is branched.

CH3
I
CH2- CH2- CH2 CH3- CH2- CH2- CH- CH3
I I
CH2-CH3 CH3

This is one continuous This is a branched

chain of carbon atoms. chain of carbon atoms.

Now that you have mastered the straight-chain (or should we say "continuous" chain) alkanes, it is
time to try something more challenging. Most alkanes exist as "branched" molecules such as the one
shown below. The longest continuous chain of carbon atoms in the molecule below is 7 (enclosed by
box). Therefore, the parent compound here is heptane. (Remember, the longest continuous chain is not
necessarily straight!)

CH2- CH3
_..~.,_~-,,,,_--~.,_~d I
- CH- CH CH3
CH2- CH3
The longest continuous chain contains 7 carbon's.

Having identified the parent compound, we must next identify the side chains. These side chains are
commonly called alkyl groups. Alkyl groups are attached to the longest continuous chain. When written
alone, they are usually shown with a free-bonding site represented by a dash (like this: -CH3). This
bonding site represents a spot where a hydrogen atom has been removed. Thus, the general formula for
the alkyl groups is CnH2n+1. The free bonding site is what allows the alkyl group to bond to the parent
compound. Alkyl groups are named with the same prefixes as the alkanes themselves. The suffix is
changed from "ane" to "yl." Complete Problem 3 below by entering the formulas and condensed
structural formulas of the first six alkyl groups.

Problem 3. Complete the exercise below.

Name of Alkyl group Condensed Structural Formula

a. methyl -CH3

b. ethyl -CH2CH3
c. propyl -CH2CH2CH3
d. butyl

e. pentyl -CH2CH2CH2CH2CH3
f. hexyl -CH2CH2CH2CH2CH2CH3
25-6 ©1997, A.J. Girondi
Depending on where the hydrogen atom is removed, the bonding site on some alkyl groups can change
position. This would change the way in which the alkyl group bonds to the parent compound. For
example, note the two alkyl groups shown below. Both are composed of three-carbon chains, but the
bonding site differs:
I
- CH2- CH2- CH3 CH3- CH- CH3
propyl isopropyl

The compound on the left below has a propyl group attached to the parent compound which is octane.
The compound on the right has an isopropyl group attached to the parent compound (heptane). Note
that all carbons in the molecules have four bonds.

CH3
I
CH2
I
CH2 CH3- CH- CH3
I I
CH3-CH2- CH2- CH- CH2-CH2- CH2-CH3 CH3- CH2- CH2- CH- CH2- CH2- CH2- CH3
Propyl group attached to an 8-carbon chain lsopropyl group attached to an 8-carbon chain

The carbon atoms on the end of the chain are called terminal carbons. When the bonding site of an alkyl
group occurs on a terminal carbon, the alkyl group is said to be "normal" and its name is sometimes
preceded by the letter n. Thus, the propyl group above could also be called n-propyl (pronounced
"normal propyl"). We will consider the use of this "n" prefix as optional. The other structure with the
bonding site on the center carbon is called isopropyl.

SECTION 25.4 IUPAC Rules for Naming Alkanes

A system for naming organic compounds has been developed by the International Union of Pure
and Applied Chemists (IUPAC). The system is accepted and used throughout the world. There is also a
method by which many organic compounds are given "common" names, but we will use only the IUPAC
system in this chapter. We will consider the rules one at a time and apply them to some practice problems.

RULE 1: Locate the longest continuous chain of carbon atoms. This will give you the name of the
"parent" compound.

For example, if the longest chain contains four carbons, the parent compound is butane. The longest
chains in the following two molecules are enclosed by a box:

CH2-CH3
CH3
I CH3 CH- CH - CH-CH -
CH2 I
I
CH2 CH2-CH3 '
I
CH- CH2- CH2- CH CH2- CH3
=
longest continuous chain 8 carbons
I
CH2- CH2-CH2- C
longest continuous chain =11 carbons
25-7 ©1997, A.J. Girondi
Problem 4. Draw a box around the longest continuous chain of carbon atoms in the structures below,
and name the parent compound for each one.

CH3 CH3
I I
a. CH3- CH2- CH2- CH- CH3 b. CH3- CH c. CH3- CH2- CH- CH2- CH3
I I
CH3 CH2- CH2- CH3

CH2- CH3 CH3

I I
d. CH3- CH- CH2- CH- CH3 e. CH3- CH- CH2- CH3 f. CH3- C- CH2- CH3
I I I
CH2- CH3 CH2- CH3 CH2
I
CH3

a. parent: pentane heptane

d. p a r e nt:------------

b. parent: -propane
----------- pentane
e. parent: - -----------

c. parent: hexane f. parent: pentane

RULE 2: The name of the parent compound is modified by noting what alkyl groups are attached to the
chain. Number the longest chain so that the alkyl group(s) will be on the lowest numbered carbons.

Note in the molecules shown below, that the longest chain should be numbered from right to left
in order to give the carbon which is bonded to the methyl group the lowest possible number:

1 2 3 4 4 3 2 1
CH3- CH2-CH- CH3 CH3-CH2- CH- CH3
I I
CH3 CH3
Incorrect Numbering Correct Numbering

The correct name of this compound is 2-methylbutane. The "2-" indicates that the methyl group is
attached to the second carbon in the longest chain. Note that the name of the alkyl group is added to that
of the parent compound (butane) to form one word, and that hyphens are used to separate numbers from
alphabetical parts of the name.

Problem 5. For the following compounds, draw a box around the longest continuous carbon chain and
name each molecule. The name of the molecule in part "b" is given to help you.

a. CH3- CH- CH2- CH2- CH3 Name: _ _ _ _ _ _ _ _ _ _ _ _ _ _ _~

2-methylpentane
I
CH3

b. CH3- CH2- CH2- CH- CH2- CH3 Name: 3-ethylhexane

I
CH3-CH2

25-8 ©1997, A.J. Girondi

 CH2- CH2- CHa
I
c. CH3- CH2- CH2- CH2- CH- CH2- CH2- CH3

4-propyloctane

CH3-CH- CH3
I
d. CH3- CH2- CH2- CH- CH2- CH2- CH2- CH2- CH3

4-Isopropylnonane

RULE 3: When the same alkyl group occurs more than once in a molecule, the numbers of the carbons to
which they are attached are all included in the name. The number of the carbon is repeated as many times
as the group appears. The number of repeating alkyl groups is indicated in the name by the use of Greek
prefixes for 2, 3, 4, 5, etc. (di, tri, tetra, penta, etc.).

To better understand rule 3, study the following examples.

CH3
I
CH3-CH-CH- CHr CH3 is called 2,3-dimethylpentane
I
CH3
Note that numbers used in the name are separated from each other by commas, and note that the
numbers are separated from the rest of the name with a hyphen.

CH2- CH3
I
c~-c~-c~-c-c~-c~ is called 3,3-diethylhexane
I
CH2-CH3

Problem 6. Name the four molecules whose structures are drawn below.

CHa CH2-CH3 CH2-CH3

I I I
a. CH3- C- CH3 b. CH3- C- CHa ~ c~-c~-c~-c~-c-c~-c~-c~
I I I
CH3 CH3- CH2 CH2-CH3

2,2-dimethylpropane
d. CH3- CH- CH2- CH2- CHa
I 2,2-diethylbutane 3,3-dimethylpentane
CH-CH3
I 4,4-diethyloctane
CH3-CH-CH3
1,1,2,3-tetramethylheptane 2,3,4-trimethyl heptane

25-9 ©1997, A.J. Girondi

RULE 4: If there are two or more different kinds of alkyl groups attached to the parent chain, name them in
alphabetical order.
CH2- CH3
I is called 3-ethyl-2-methylpentane
For example: CH3- CH- CH- CH2- CH3
I
It is NOT called 2-methyl-3-ethylpentane
CH3

However, when you are determining the alphabetical order, do not consider any Greek prefixes that are
being used. For example:

CH3 CH2-CH3
I I is called 4-ethyl-2,2-dimethylheptane
CH3- C- CH2- CH - CH2- CH2- CH3
I It is NOT called 2,2-dimethyl-4-ethylheptane
CH3

Problem 7. Name the four molecules drawn below.

a. CH3- CH2- CH2-CH- CH2- CH- CH2-CH2- CH3

I I
CH3 CH2-CH3 4-ethyl-5-methyl nonane
6-ethyl-4-methylnonane

CH3 CH2- CH2- CH3

I I
b. CH3-CH2- C-CH2-CH2-CH- CH2- CH2- CH3
I
CH3
3-dimethyl-6-propylnonane
CH2-CH3
I
c. CH3- CH2- CH- CH- CH2- CH- CH3
I I
CHr CH- CH3 CH3 4-ethyl-5-isopropyl-2-methylheptane

CH3 CH3
I I
d. CH3- CH- CH2-CH- CH2- CH2-CH- CH3
I
CH2-CH3
4-ethyl-2,7-dimethyloctane

RULE 5: To put the finishing touches on the name of an alkane, keep the following points in mind: (a)
hyphens are used to separate numbers from names of substituents; (b) numbers are separated from each
other by commas; (c) the last alkyl group to be named is prefixed to the name of the parent alkane, forming
one word; and (d) the suffix "-ane" indicates that the molecule is an alkane.

ACTIVITY 25.5 Using Molecular Models

The structure of alkanes is more understandable if you see them in three dimensions. We will use
molecular model kits for this purpose. Obtain a box containing a molecular model kit and determine which
parts represent carbon atoms, hydrogen atoms, carbon to carbon bonds, and carbon to hydrogen bonds.
When you have done this, assemble models of the six molecules drawn in Problem 4. Pick up one of your

25-10 ©1997, A.J. Girondi

models and rotate one section of the model while holding the other. Do you see how rotation is possible
around a single bond? yes . Holding the model with both hands, bend and flex it a bit. Note
the bond angles between the carbons themselves and between the carbons and the hydrogens. Do you
see why these molecules are not really "straight" chains? _yes _ _ _ __

Because free rotation is possible around a single bond, what can you conclude about the 2 molecules
shown below?(1 they can be the same If you named these two molecules, what would
you discover?{2,__same
___ _ _ _ _ _ _ _ What
name is the name?{3L--------------
2,4-dimethylpentane
CH3
I
CH3- CH- CH2- CH- CH3 CHrCH- CH2- CH- CH3
I I I
CH3 CH3 CH3

SECTION 25.6 Cyclic Alkanes

The compounds we have studied so far have been either "straight" or "branched" chains. Carbon
atoms can also form rings which result in the formation of cyclic alkane molecules with the general formula,
CnH2n. Naming the cyclic alkanes is not difficult, but the rules do differ a bit from those used to name the
straight and branched chained compounds.

The name of a cyclic molecule requires the addition of the prefix "cyclo" to the name of the
hydrocarbon. Note the two condensed structural formulas below.

cyclopropane cyclobutane

To make cyclic compounds easier to draw, a shorthand notation is used in which the hydrogens and
carbons which are part of the ring are not represented at all. The rings are represented by lines, and a
carbon atom is assumed to be present at each angle in the ring. The proper number of hydrogen atoms is
assumed to be attached to each carbon.

For example:

cyclopropane
C3H5
D
cyclobutane
C4Hs
cyclopentane
CsH10
cyclohexane
C5H12

Name this compound _ . {4,__ _ _ _ _ _ _ _ _ _ __

cyclooctane

25-11 ©1997, A.J. Girondi

 Like the "straight-chained" compounds, cyclic molecules can also contain alkyl side chains. The
same general rules for alkane nomenclature apply to the cyclics, except that all positions in a ring are
equivalent, so a number is not needed to indicate the position of the alkyl group jf there is only one alkyl
group on the ring. For example:

-+- This is called methylcyclohexane

(It is NOT called 1-methylcyclohexane)

The carbon on which the alkyl group is located is automatically assumed to be number 1.

Problem 8. Name the cyclic molecules below.

a. ethylcyclobutane b. ethylcyclopropane c. propylcyclopentane

If there are two or more substituents on a ring, numbers must be used to indicate their positions.
One of the substituents is always assigned position number 1, and starting at position 1, the chain is
numbered either clockwise or counterclockwise so as to give the other substituents on the ring the
smallest possible numbers. For example:

CH3
I

OCH2-CH, ..____ This is called 1-ethyl-2-methylcyclopentane

..____ This is called 1,2-dimethylcyclopentane

(It is NOT called 1,5-dimethylcyclopentane)

~ This is called 1-ethyl-4-methylcyclohexane

(You may have wanted to call it 4-ethyl-1-methylcyciohexane,

but we chose to assign the number 1 position to ethyl since it
comes first, alphabetically, and since we get the same
numbers, 1 and 4, either way.)

~ This is called 4-ethyl-1,2-dimethylcyclopentane

25-12 ©1997, A.J. Girondi

In the last example, we assign position 1 to the carbon in the lower right corner and number the ring
counterclockwise. This gives the lowest possible set of numbers for the three substitutents on the ring.

C H 3 D CH2-CH3 ....___ This is called 3-ethyl-1, 1,2-trimethylcyclobutane

(We numbered clockwise this time)

CH3-I
CH3

In the molecule drawn above, if we assigned position #1 to the carbon which is bonded to the ethyl group,
we would have had to number counterclockwise and name the molecule: 1-ethyl-2,3,3-trimethylbutane.
This was avoided because it resulted in higher numbers.

The three structures drawn below are identical. Write the name: {5) 1,1,2-trimethylcyclobutane

O CH3

CH3
CH3

Problem 9. Name the cyclic alkanes shown below:

c.

CH3-L__l CH3
CH2-CH3
I

/\ d. 0 CH2- CH3

CH2-CH3

CH3
I

e. CH30CH3
f. o~:, g. ( Y C H 2 - CH2- CH3

CH3 CH3 --·~CH3

1,3-diethyl-5-methylcyclohexane 1,3,5-trimethylcyclohexane
1,2-dimethylcyclopropane f. 1-isopropyl-3-methylcyclobutane
2-ethyl-1,3-dimethylcyclopropane 1-methyl-2-propylcyclooctane
1,2-diethylcyclopentane

25-13 ©1997, A.J. Girondi

ACTIVITY 25. 7 Models of Cyclic Alkanes

Using a molecular model kit, construct the four cyclic molecules drawn below. The models give
you some idea of what these cyclic compounds look like in three dimensions. You will also see the effects
of the bond angles on the shapes of the molecules. Be sure to include all needed hydrogen atoms, even
if they are not shown on the drawings.

cyclopropane
C3H5
D
cyclobutane
C4Ha
cyclopentane
CsH10
cyclohexane
C5H12

Do any of these cyclic compounds have what you might consider to be flat rings? If so, which one(s)?

cyclobutane, cyclopentane, and cyclohexane

{6L_ _ _ __

Here is a summary of the rules used to name alkanes:

RULE 1: Locate the longest continuous chain of carbon atoms. This will give you the name of the
"parent" compound.

RULE 2: The name of the parent compound is modified by noting what alkyl groups are attached to the
chain. Number the longest chain so that the alkyl group(s) will be on the lowest numbered carbons.

RULE 3: When the same alkyl group occurs more than once in a molecule, the numbers of the carbons to
which they are attached are all included in the name. The number of the carbon is repeated as many times
as the group appears. The number of repeating alkyl groups is indicated in the name by the use of Greek
prefixes for 2, 3, 4, 5, etc. (di, tri, tetra, penta, etc.).

RULE 4: If there are two or more different kinds of alkyl groups attached to the parent chain, name them in
alphabetical order.

RULE 5: The put the finishing touches on the name of an alkane, keep the following points in mind: (a)
hyphens are used to separate numbers from names of substitutents; (b) numbers are separated from
each other by commas; (c) the last alkyl group to be named is prefixed to the name of the parent alkane,
forming one word; and (d) the suffix "-ane" indicates that the molecule is an alkane.

SECTION 25.8 Naming Alkenes

Now that you are an expert on alkanes, let's take a look at the alkene functional group. A
functional group is a feature of a class of compounds that is responsible for its characteristic properties.
The functional group of the alkanes is the single bond. The functional group of the alkenes is the double
bond. Alkenes contain at least one double bond which exists between a pair of carbon atoms. The
general formula for the straight-chained alkenes is CnH2n. The suffix to be used in the names of alkenes is
"-ene." The rules for naming alkenes are the same as those for alkanes with a few additional restrictions.
25-14 ©1997, A.J. Girondi
Additional Rules for the Nomenclature of Alkenes:

RULE 1: The chain chosen as the parent chain must contain the carbon-carbon double bond (C=C).

RULE 2: The parent chain must be numbered to give the carbon-carbon double bond the lowest possible
number.

RULE 3: The name of the alkene must contain a number to indicate the position of the double bond.

Note the example below. The longest carbon chain alkene is numbered correctly, giving the double bond
the lowest possible number.

2 1
CH2-CH3
7 6 5 4 I As we number the carbons, the first carbon involved in the
CH3-CH2-CH-CH= C-CH3 double bond is #3, so the parent chain is called 3-heptene.
I 3 Methyl groups are located on carbons #3 and #5.
CH3
3,5-dimethyl-3-heptene

A number is not used to locate the double bond in chains which are shorter than four carbons. Two
examples are below.
....._ This is called ethene, not 1-ethene

CHr CH= CH2 ....._This is called propene, not 1-propene

Why is it that these two molecules do not require the use of the number? {?,___ _ _ _ _ _ _ _ __

the chain will be the same, wherever you put the double bond, wouldn't make a difference.

Problem 10. Name the alkenes below. After you have located the longest chain containing the double
bond, be sure to number the chain so that the double bond gets the lowest possible number.

a. CH3- CH2- CH= CH2 but-1-ene

b. CH3- CH= CH - CH3 but-2-ene
c. CH3- CH2- CH= CH - CH3 pent-2-ene
d. CH3- CH2- CH= CH-CH2- CH3 hex-3-ene
e. CH2= CH2 ethene
f. CH3- CH= CH2 propene

CH3
I
g. CHr CH-CH2- CH-CH= CH2 3,5-dimethylhex-1-ene
I
CH3

25-15 ©1997, A.J. Girondi

h. CH3- C= CH- CH3
I 3-methylpent-2-ene
CH2-CH3

i. CH3- CH- CH= CH2

I 3-methylbut-1-ene
CH3

CH2-CH3
I
j. CH3- CH= CH- c- CH2- CH3
I 4,4-diethylhex-2-ene
CH2-CH3

SECTION 25.9 Naming Cycloalkenes

Cycloalkenes are named similarly to straight chained alkenes. The carbons in the ring that contain
the double bond are always assigned the #1 and #2 positions, so numbers are used only to locate the
positions of substitutents attached to the ring - not to locate the position of the double bond. The general
formula for cyclic alkenes in CnH2n-2. Study the examples below.

CH3

Dcyclobutene
0 CH3
3-methylcyclohexene
6CH3
3,4-dimethylcyclopentene

Problem 11. Name the following cycloalkenes.

a. o-CH2-CH3 3-ethyl cyclopentene

b.
5-ethyl-2,2-dimethylcyclohexene

c.
2,4-dimethylbutene

25-16 ©1997, A.J. Girondi

d.
2-isopropylcyclopropene

e. C y
--·~CH3
CH2- CH2- CH3

2,4-dimethyl-5-propylcyclooctane

CH3

f. D -CH2-CH3

- CH2- CH2- CH2- CH3

1-butyl-2-ethylcyclobutene

SECTION 25.10 Naming Alkynes

The functional group of the compounds known as the alkynes is a triple bond. The general
formula for straight-chained alkynes is CnH2n-2. Alkynes are named in much the same way as the alkenes,
except that their names end with the suffix "-yne", signifying the triple bond. Once again, the triple bond
must be located within the parent chain, and it should be assigned the lowest possible number.

Additional Rules for the Nomenclature of Alkynes:

RULE 1: The chain chosen as the parent chain must contain the carbon- carbon triple bond.

RULE 2: The parent chain must be numbered to give the carbon-carbon triple bond the lowest possible
number.

RULE 3: The name of the alkyne must contain a number to indicate the position of the triple bond.

As was the case with the alkenes, no number is used to locate the triple bond if the parent chain is shorter
than four carbons:

cH::cH CH_ C- CH3 CH:: c- CH2- CH3 CH3- C_ C- CH3

ethyne propyne 1-butyne 2-butyne

1 2 3 4 5 6

For the example at right, the correct name is 5-methyl-2-hexyne __.

CH3- c::: C- CH2- C- CH3
I
CH3

25-17 ©1997, A.J. Girondi

Problem 12. Name the alkynes drawn below. Be sure to number the parent chain so as to give the
triple bond the lowest possible number.

a. CH- C-CH2-CH2-CH3 pent-1-yne

b. CH3-CH2-CH2-c:= C-CH3 hex-2-yne
c. CH3-CH2-c:= C-CH3 pent-2-yne

pent-1-yne

hept-2-yne

f. CH3- CH- c:= CH 3-methylbut-1-yne

I
CH3
CH3
I
g. CH3- CH2- CH- CH- c:= CH 4-ethyl-3-methylhex-1-yne
I
CH2-CH3

CH3
I
h. cH=c-c-CH3 3,3-dimethylhex-1-yne
I
CH2- CH2- CH3

CH3
I
i. CH3- c= c- CH- CH2-CH- CH3 6-methyl-4-propylhept-2-yne
I
CH2- CH2- CH3

Table 25.1
Summary of General Formulas for
Alkanes, Alkenes, and Alkynes

Class of Compound General Formula

Straight-chained alkanes CnH2n+2

Cycloalkanes CnH2n
Alken es CnH2n
Cycloalkenes CnH2n-2
Alkynes CnH2n-2

25-18 ©1997, A.J. Girondi

 SECTION 25.11 Review Problems

Problem 13. The names of the compounds listed below are NOT correct. Using the incorrect name,
draw the structural formula in the work area. Then write the correct name of each compound on the line
provided.

Incorrect Name Correct Name Work Area

a. 4,4-dimethylhexane 3-dimethylhexane

b. 2-n-propylpentane 2,n-propylhexane

c. 1, 1-diethylbutane 3-ethylhexane

d. 1,4-dimethylcyclobutane 1,2-dimethylcyclobutane

e. 3-methyl-2-butene 2-methyl-but-2-ene

f. 5-ethylcyclopentene 2-ethylcyclopentene

g. 2-n-propyl-1-propene 2-methylpentane

h. 2-isopropyl-3-heptene 2,3-dimethylhept-3-ene

i. 2,2-dimethyl-3-butyne 3,3-dimethylbut-1-yne

j. 5-octyne oct-3-yne
25-19 ©1997, A.J. Girondi
 Problem 14. Write condensed structural formulas for the following:

Name Condensed Structural Formula

CH3CH2CH2CH(CH3CHCH3)CH2CH2CH2CH3
a. 4-isopropyloctane

n(CH2CH2CH3)
b. 3,4-dimethyl-4-n-propylheptane
CH3CH2CH(CH3)CH(CH3)CH2CH2CH3

c: 1, 1-dimethylcyclobutane CH2CH(CH3)
CH2CH2 (CH3)

CH2CH3
d. 3-ethyl-3-heptene CH3CH2CH=CHCH2CH2CH3

e. 3-ethyl-2-methyl-1-hexene CH2=C(CH2)CH(CH2CH3)CH2CH2CH3

f. 3-octene CH3CH2CH=CHCH2CH2CH2CH3

- CH3
CH=CCCH3
g. 3,3-dimethyl-1-butyne
CH3

- CH3
h. 4,4-dimethyl-2-pentyne
CH3C=CCCH3
CH3

n(CH2CH2CH2CH3)
i. 3-n-butyl-2-ethylcyclohexene CH2 CH
CH2 CH(CH2CH3)
CH2 CH2
j. 3,4-diethyl-4,6-dimethylnonane

CH3CH2CH(CH2CH3)C(CH2CH3)CH2CH2CH(CH3)CH2CH3
CH2
25-20 ©1997, A.J. Girondi
SECTION 25.12 Learning Outcomes

Before leaving this chapter, read through the learning outcomes listed below. Place a check
before each outcome when you feel you have mastered it. When you have completed this task, arrange
to take any quizzes or exams on this chapter, and move on to Chapter 26.

1. Distinguish between organic and inorganic compounds.

_ _2. Distinguish between alkanes, alkenes, and alkynes.

_ _3. Determine the number of carbon atoms in the longest chain of any alkane, alkene, or alkyne.

_ _4. Use the IUPAC system to name alkanes, alkenes, and alkynes, given their condensed structural
formulas.

_ _5. Given the IUPAC names, be able to draw condensed structural formulas for alkanes, alkenes,
and alkynes.

25-21 ©1997, A.J. Girondi