Chapter 11 Introduction to

Organic Chemistry: Alkanes

11.3
Alkanes with Substituents

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 Isomers of Butane
Isomers
 have the same molecular
formula
 have different structural
arrangements
 of butane (C4H10) consist
of a straight chain and a Branch or
branched chain each with substituent

4 carbon atoms

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Substituents
Substituents are
 attached to carbon chains
 carbon branches that are missing one H and named
as alkyl groups
 halogen atoms that are named as halo substituents

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 Alkanes with Alkyl Groups
CH3

CH3—CH—CH3 methylpropane

methyl groups
CH3 CH3

CH3—CH—CH2—CH—CH3 2,4-dimethylpentane

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Naming Alkanes with Substituents

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 Example of Naming Alkanes
Give the name of CH3

CH3─CH─CH2─CH3
STEP 1 Write the name of the longest chain: butane
STEP 2 Number the chain from the end nearer a branch:
CH3

CH3─CH─CH2─CH3
1 2 3 4
STEP 3 Give location and names of substituents:
2-Methylbutane
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 Learning Check
Write the IUPAC name for:

Cl CH3

CH3─CH2─CH─CH─CH3

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 Solution
STEP 1 Write the name of the longest chain:
pentane
STEP 2 Number chain from end nearer substituents:
Cl CH3 (nearer end)

CH3─CH2─CH─CH─CH3
5 4 3 2 1

STEP 3 Give location and name substituents

alphabetically:
3-Chloro-2-methylpentane

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 Learning Check
Give the IUPAC name for each of the following:

A. CH3 CH3
| |
CH3─CH─CH2 ─CH─CH2─CH3

B. Cl CH3
| |
CH3─CH2─CH─CH2─C─CH2─CH3
|
Cl
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 Solution
A. CH3 CH3
| |
CH3─CH─CH2 ─CH─CH2─CH3 2,4-dimethylhexane
1 2 3 4 5 6

B. Cl CH3 more substituents on C3

| |
CH3─CH2─CH─CH2─C─CH2─CH3
|
Cl
7 6 5 4 3 2 1

3,5-dichloro-3-methylheptane
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Guide to Drawing Alkane Structures

General, Organic, and Biological Chemistry 11

 What Is in a Name?
The structural formula is drawn from the IUPAC name.

2,4-dimethylhexane

2,4 dimethyl hexane

Location of Two CH3-groups 6-carbon main chain
branches on attached with single C—C
bonds main chain

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 Learning Check
Draw the condensed structural formula for
3-bromo-1-chlorobutane.

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 Solution
STEP 1 Draw a chain with 4 carbon atoms:
C─C─C─C
STEP 2 Number the chain and add substituents:
Br

C ─ C ─ C ─ C ─ Cl
4 3 2 1
STEP 3 Add hydrogen (H) to give four bonds to each C:
Br

CH3─CH─CH2─CH2─Cl
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 Naming Cycloalkanes with
Substituents
The name of a substituent is placed in front of the
cycloalkane name.
CH3
Methylcyclobutane

When there are two substituents, number the ring

1-bromo-2-chlorocyclopentane
Br

Cl

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 Learning Check
Name each of the following:

1. CH3

CH2─CH3
2.

Cl

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 Solution
Name each of the following:

1. CH3 methylcyclopropane

CH2─CH3
2.

Cl 3-Chloro-1-ethylcyclohexane

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 Learning Check
Write three isomers of C5H12, and name each.

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 Solution
A chain of 5 carbon atoms: CH3─CH2─CH2─CH2─CH3
pentane
A chain of 4 carbon atoms and 1 carbon branch:
CH3
│
CH3─CH─CH2─CH3 2-methylbutane

A chain of 3 carbon atoms and 2 carbon branches:

CH3
│
CH3─C─CH3 2,2-dimethylpropane
│
CH3
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