Chapter 10 Introduction to Organic Chemistry: Alkanes 10.

2 Alkanes

Copyright 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings

Structural Formulas
Alkanes are written with structural formulas that are expanded to show each bond. condensed to show each carbon atom and its attached hydrogen atoms.

Expanded H
H C H H

Condensed

CH4 , methane

Expanded and Condensed Structures

Structural Formulas
Condensed formulas are written for expanded structural formula by showing each carbon and the attached hydrogen atoms. Expanded Condensed

H H H H HC C C C H H H H H

CH3CH2CH2CH3

Names of Alkanes
The names of alkanes are determined by the IUPAC (International Union of Pure and Applied Chemistry) system. end in ane. with 1-4 carbons in a chain use prefixes as follows. Name # Carbons Methane 1 Ethane 2 Structural Formula CH4 CH3CH3

Propane
Butane

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4

CH3CH2CH3
CH3CH2CH2CH3
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Names of Alkanes
Alkanes with 5-10 carbon atoms in a chain use Greek prefixes. Name # Carbons Structural Formula Pentane 5 Hexane 6 Heptane 7 Octane 8 CH3CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH2CH2CH3

Nonane 9

CH3 CH2 CH2CH2CH2CH2CH2CH2CH3

Decane 10 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3
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Learning Check
A. Write the condensed formula for: H H H H H H C C C C C H

H H H H H B. What is its molecular formula? C. What is its name?

Solution
A. CH3CH2CH2CH2CH3 B. C5H12 C. pentane

Writing Structural Formulas

Carbon atoms in a chain maintain tetrahedral shape. are connected in a zig-zag pattern. are drawn as 2-dimensional. Ccan be written in several conformations.

Some Structures for Butane

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Hexane has Six Carbon Atoms

Hexane is an alkane with six carbon atoms in a continuous chain. has a zig-zag look because each carbon atom is at the center of a tetrahedron. is represented by a ball-and-stick model as shown below.

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Learning Check
Write the condensed structural formula for A. ethane.

B. heptane.

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Solution
Write the condensed structural formula for A. ethane CH3CH3

B. heptane CH3CH2CH2CH2CH2CH2CH3

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Cycloalkanes
Cycloalkanes are cyclic alkanes. have two hydrogen atoms fewer than the open chain. are named by using the prefix cyclo- before the name of the alkane chain with the same number of carbon atoms.

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Cycloalkanes
The structural formulas of cycloalkanes are usually represented by geometric figures, Cyclopropane CH2

CH2
Cyclobutane CH2 CH2

CH2
CH2 CH2

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More Cycloalkanes
Cyclopentane CH2 CH2 CH2 CH2 CH2

Cyclohexane

CH2 CH2 CH2 CH2 CH2 CH2

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Learning Check
Name the following. A. CH3CH2CH2CH3 B. C. CH3CH2CH2CH2CH2CH2CH2CH3 D.

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Solution
Name the following: A. CH3CH2CH2CH3 B. butane cyclopropane

C. CH3CH2CH2CH2CH2CH2CH2CH3 octane D.

cyclohexane

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