Naming of Alkane Alkene Alkyne

Organic Chemistry
Third Edition
David Klein
Chapter 4
Alkanes and Cycloalkanes
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
4.1 Alkanes
• Hydrocarbons –composed of hydrogen and carbon
• Hydrocarbons are saturated or unsaturated
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. 4-2 Klein, Organic Chemistry 3e
4.5 Sources and Uses of Alkanes
• Gasoline is a mixture of straight, branched, and aromatic
hydrocarbons (5-12 carbons in size)
• Large alkanes can be broken down into smaller molecules by
Cracking
• Straight chain alkanes can be converted into branched alkanes

and aromatic compounds through Reforming
• After using these processes, the yield of gasoline is about 47%

rather than 19%
4.5 Sources and Uses of Alkanes
• various components of petroleum are separated by distillation
• The gasoline fraction of crude oil only makes up about 19%,

which is not enough to meet demand
4.3 Constitutional Isomers
• ISOMERS
– different structures, same molecular formula
• CONSTITUTIONAL ISOMERS
– different connectivity of atoms
4.3 Constitutional Isomers
• As the number of carbon atoms increases, the number of
constitutional isomers increases
4.1 Naming Alkanes
• Many organic compounds have “common” names
4.2 IUPAC Nomenclature - Alkanes
• The IUPAC system – systematic naming of compounds
• IUPAC name includes:
– Parent name (longest carbon chain)

– Names of substituents
– Location of substituents
4.2 Selecting the Parent Chain
1. Identify the parent chain - the longest consecutive chain of
carbons
non pentacont
dec
hect

carbons
If there is more
is a competition than two
between one chains
possibleofparent
equal chain,
length,choose the onethe ch
then choose
with the mostSubstituents
er of substituents. substituents are
attached
branches connected to the parent cha
Correct Incorrect
(3 substituents) (2 substituents)
m “cyclo” is used to indicate the presence of a ring in the structure of a

e compounds are called cycloalkanes:
4-10 Klein, Organic Chemistry 3e
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved.
carbons
If the parent chain is cyclic, add the prefix “cyclo”
• Practice with Skillbuilder 4.1
• Practice the Skill 4.1 – Identify and name the parent in each of the
following compounds
hexane heptane Cycloheptane
4.2 Naming Substituents
2. Identify and name the substituents
Substituents end in yl instead of ane.
A ring can be either a parent chain or a substituent depending on the
number of carbons

– For substituents with complex branches
1 2 3 4
1. Number the longest carbon chain WITHIN the substituent. Start

with the carbon attached to the parent chain
2. Name the substituent (in this case butyl)
3. Name and Number the substituent’s side group (in this case 2-
methyl)
The name of the substituent is (2-methylbutyl)
– Some branched substituents have common names
– Two types of propyl groups
– Some branched substituents have common names
– Three types of butyl groups
4.2 Assembling the IUPAC Name
• Carbons in the parent chain have to be numbered
• 2-methylpentane means there is a methyl group on carbon #2 of

the pentane chain
• Guidelines to follow when numbering the parent chain
1. If ONE substituent is present, number the parent chain so that

the substituent has the lowest number possible
2. When multiple substituents are present, number the parent

chain to give the first substituent the lowest number possible
3. If there is a tie, then number the parent chain so that the

second locant gets the lowest number possible
4. If there is no other tie-breaker, then assign the lowest number

alphabetically
– The same rules apply for cycloalkanes
To assemble the complete name:
1. Put the # and name of each substituent before the parent

chain name, in alphabetical order
5. A prefix is used (di, tri, tetra, penta, etc.) if multiple

substituents are identical.
note: “di” or “tri” is ignored when alphabetizing the

substituents
4.2 IUPAC Rules - Summary
1. Identify the parent chain
2. Identify and Name the substituents
3. Number the parent chain; assign a locant to each substituent
4. List the numbered substituents before the parent name in

alphabetical order
• Practice with SkillBuilder 4.4
4.2 IUPAC Rules - Summary
• Following the rules, we can name the following compound:
Parent name:
cyclohexane
1
6 2 Substituents:
1-tert-butyl
5 4 3 2-ethyl
4-methyl
4,4-dimethyl
4-methyl
1-tert-butyl-2-ethyl-4,4-dimethylcyclohexane
Sample Problem
PROBLEM: Give the systematic name for each of the following
Klein, Organic Chemistry 3e

Sample Problem 15.2
SOLUTION:
2,2-dimethylbutane
3,4-dimethylhexane
1-ethyl-2-methylcyclopentane

Sample Problem

Sample Problem

ALKENES
• A hydrocarbon that contains at least one C=C
bond is called an alkene.
• Alkenes are unsaturated and have the general
formula CnH2n.
• Alkenes are named using a series of rules similar
to those for alkanes, with the suffix -ene used
instead of -ane to identify the family. There are
three steps.
NAMING OF ALKENES
• STEP 1 Name the parent hydrocarbon. Find the longest
carbon chain containing the double bond, and name
the compound accordingly, using the suffix -ene:
NAMING OF ALKENES
• STEP 2 Number the carbon atoms in the chain. Begin at
the end nearer the double bond or, if the double bond
is equidistant from the two ends, begin at the end
nearer the first branch point. This rule ensures that the
double-bond carbons receive the lowest possible
numbers.
NAMING OF ALKENES
• STEP 3 Write the full name.
Number the substituents
according to their positions
in the chain, and list them
alphabetically. Indicate the
position of the double bond
by giving the number of the
first alkene carbon and
placing that number directly
before the parent name. If
more than one double bond
is present, indicate the
position of each and use one
of the suffixes -diene, -triene,
and so on.
NAMING OF ALKENES
• Cycloalkenes are named similarly to open-chain alkenes but,
because there is no chain end to begin from, we number the
cycloalkene so that the double bond is between C1 and C2 and the
first substituent has as low a number as possible. Note that it’s not
necessary to indicate the position of the double bond in the name
because it is always between C1 and C2.
Sample Problem

Sample Problem
3-methyl-1-pentene
cis-2,3-dimethyl-3-hexene trans-2,3-dimethyl-3-hexene

Organic Chemistry
Third Edition
David Klein
Chapter 9
Alkynes
Copyright © 2017 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 3e
10.1 Alkynes
• Alkynes are molecules that possess a CºC triple bond
9.1 Alkynes
• Given the presence of pi bonds, alkynes are similar to alkenes in
their ability to act as a nucleophile
• Many of the addition reactions of alkenes also work on alkynes
9.1 Alkynes in Industry and Nature
• Acetylene is the simplest alkyne
• It is used in blow torches and as a precursor for the synthesis of
more complex alkynes
• More than 1000 different alkyne natural products have been
isolated
9.1 Alkynes
• An example of a synthetic alkyne is ethynylestradiol
• Ethynylestradiol is the active ingredient in many birth control pills
9.2 Nomenclature of Alkynes
• Alkynes are named using the same procedure we used in Chapter
4 to name alkanes with minor modifications
1. Identify the parent chain, which should include the CºC triple
bond
2. Identify and Name the substituents
3. Assign a locant (and prefix if necessary) to each substituent
giving the CºC triple bond the lowest number possible
alphabetical order. Ignore prefixes (except iso) when ordering
alphabetically
5. The CºC triple bond locant is placed either just before the
parent name or just before the -yne suffix
1. Identify the parent chain, which should include the CºC triple
bond
2. Identify and name the substituents.
3. Assign a locant (and prefix if necessary) to each substituent
giving the CºC triple bond the lowest number possible
– The locant is ONE number, NOT two. Although the triple bond
bridges carbons 2 and 3, the locant is the lower of those two
numbers
alphabetical order. Ignore prefixes (except iso) when ordering
alphabetically
5. The CºC triple bond locant is placed either just before the
parent name or just before the -yne suffix
• common names derived from acetylene are often used as well
• Alkynes are also classified as terminal or internal
• Practice with SkillBuilder 9.1

Sample Problem
2,5-Dimethyl-3-hexyne 3,3-Dimethyl-1-butyne

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Organic Chemistry

• Hydrocarbons are saturated or unsaturated

• Straight chain alkanes can be converted into branched alkanes

• After using these processes, the yield of gasoline is about 47%

• The gasoline fraction of crude oil only makes up about 19%,

• IUPAC name includes:

– Parent name (longest carbon chain)

1. Identify the parent chain - the longest consecutive chain of

m “cyclo” is used to indicate the presence of a ring in the structure of a

• Practice with Skillbuilder 4.1

hexane heptane Cycloheptane

Substituents end in yl instead of ane.

• Practice with Skillbuilder 4.2

1. Number the longest carbon chain WITHIN the substituent. Start

• Practice with Skillbuilder 4.3

• 2-methylpentane means there is a methyl group on carbon #2 of

1. If ONE substituent is present, number the parent chain so that

2. When multiple substituents are present, number the parent

3. If there is a tie, then number the parent chain so that the

4. If there is no other tie-breaker, then assign the lowest number

– The same rules apply for cycloalkanes

1. Put the # and name of each substituent before the parent

5. A prefix is used (di, tri, tetra, penta, etc.) if multiple

note: “di” or “tri” is ignored when alphabetizing the

2. Identify and Name the substituents

3. Number the parent chain; assign a locant to each substituent

4. List the numbered substituents before the parent name in

• Practice with SkillBuilder 4.4

PROBLEM: Give the systematic name for each of the following

Klein, Organic Chemistry 3e

Klein, Organic Chemistry 3e

PROBLEM: Give the systematic name for each of the following

Klein, Organic Chemistry 3e

PROBLEM: Give the systematic name for each of the following

Klein, Organic Chemistry 3e

PROBLEM: Give the systematic name for each of the following

Klein, Organic Chemistry 3e

Klein, Organic Chemistry 3e

• Many of the addition reactions of alkenes also work on alkynes

2. Identify and name the substituents.

• Alkynes are also classified as terminal or internal

• Practice with SkillBuilder 9.1

Klein, Organic Chemistry 3e

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