Chapter 2

Alkanes: The Nature of

Organic Compounds
Jae Woong Jung
Kyung Hee University

에너지나노소재연구실
Energy Nanomateials Laboratory
2. Alkanes: The Nature of
Organic Compounds
Why this Chapter
 Alkanes are unreactive, but provide useful vehicle to
introduce important ideas about organic compounds

 Alkanes will be used to discuss basic approaches to naming

organic compounds

 We will take an initial look at 3-D aspects of molecules

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 2.1 Functional Groups
 Functional group - collection of atoms at a site that have a
characteristic behavior in all molecules where it occurs
 For example, the double bonds in simple and complex alkenes
react with bromine in the same way

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Table 2-1c, p. 41
Table 2-1d, p. 41
Functional Groups with Carbon–Carbon Multiple
Bonds
 Alkenes have a C-C double bond
 Alkynes have a C-C triple bond
 Arenes have special bonds that are represented as
alternating single and double C-C bonds in a six-
membered ring

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Functional Groups with Carbon Singly Bonded
to an Electronegative Atom

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Functional Groups with a Carbon–Oxygen
Double Bond (Carbonyl Groups)

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2.2 Alkanes and Alkyl Groups: Isomers
 Alkanes: Compounds with C-C single bonds and C-H
bonds only (no functional groups)
 Connecting carbons can lead to large or small molecules
 The formula for an alkane with no rings in it must be
CnH2n+2 where the number of C’s is n
 Alkanes are saturated with hydrogen (no more can be
added
 They are also called aliphatic compounds

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 Alkane Isomers
 CH4 = methane, C2H6 = ethane, C3H8= propane
 The molecular formula of an alkane with more than
three carbons can give more than one structure
 C4 (butane) = butane and isobutane
 C5 (pentane) = pentane, 2-methylbutane, and 2,2-
dimethylpropane
 Alkanes with C’s connected to no more than 2 other
C’s are straight-chain or normal alkanes
 Alkanes with one or more C’s connected to 3 or 4 C’s
are branched-chain alkanes
 Isomers that differ in how their atoms are arranged in
chains are called constitutional isomers

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Condensed Structures of Alkanes
 We can represent an alkane in a brief form or in
many types of extended form
 A condensed structure does not show bonds but lists
atoms, such as
 CH3CH2CH2CH3 (butane)
 CH3(CH2)2CH3 (butane)

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 Alkyl group – remove one H from an alkane (a part of a
structure)
 General abbreviation “R” (for Radical, an incomplete
species or the “rest” of the molecule)
 Name: replace -ane ending of alkane with -yl ending
 CH3 is “methyl” (from methane)
 CH2CH3 is “ethyl” from ethane

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 Types of Alkyl groups
 Classified by the connection site
 a carbon at the end of a chain (primary alkyl group)
 a carbon in the middle of a chain (secondary alkyl group)
 a carbon with three carbons attached to it (tertiary alkyl
group)

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 2.3 Naming Branched-Chain Alkanes
 Compounds are given systematic names by a process that uses
IUPAC rule

1. Find parent hydrocarbon chain

2. Number the atoms in the main chain
3. Identify and number the substituents
4. Write the name as a single word

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1. Find parent hydrocarbon chain

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2. Number the atoms in the main chain

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3. Identify and number the substituents

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 4. Write the name as a single word

Use the appropriate multiplier prefixes di-, tri-, tetra-, and so forth

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Common names

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2.4 Properties of Alkanes
Fractional distillation separates petroleum into fractions
according to boiling point.

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 Alkanes are sometimes called paraffins (low
affinity compounds) because they do not react
as most chemicals
 They will burn in a flame, producing carbon
dioxide, water, and heat
 They react with Cl2 in the presence of light to
replace H’s with Cl’s (not controlled)

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 2.5 Conformations of Ethane
 Stereochemistry concerned with the 3-D aspects
of molecules
  bonds are cylindrically symmetrical
 Rotation is possible around C-C bonds in open-
chain molecules

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 Conformation- Different arrangement of
atoms resulting from bond rotation
 Conformations can be represented in 2 ways:

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 There is a barrier to rotation, and some
conformers are more stable than others
 Staggered- most stable: all 6 C-H bonds are
as far away as possible
 Eclipsed- least stable: all 6 C-H bonds are as
close as possible to each other

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2.6 Drawing Chemical Structures

Skeletal structure

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2.7 Cycloalkanes

 Cycloalkanes are saturated cyclic hydrocarbons

 Have the general formula (CnH2n)

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 Naming Cycloalkanes
1. Find the parent. # of carbons in the ring.

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2. Number the substituents, and write the name

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 2.8 Cis-Trans Isomerism in Cycloalkanes
 Cycloalkanes are less flexible than open-chain
alkanes
 Much less conformational freedom in
cycloalkanes

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 Because of their cyclic structure, cycloalkanes have 2 faces as
viewed edge-on
“top” face “bottom” face
- Therefore, isomerism is possible in substituted cycloalkanes
- There are two different 1,2-dimethyl-cyclopropane isomers

Cis-trans isomers
- Cis- : on the same side
- Trans- : accross
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Stereoisomerism
 Compounds which have their atoms
connected in the same order but differ in 3-D
orientation

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 2.9 Conformations of Some Cycloalkanes
Cyclopropane
 3-membered ring must have planar structure
 Symmetrical with C–C–C bond angles of 60°
 Angle strain

Structures of cyclopropane, cyclobutane and cyclopentane

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Conformations of Cyclohexane
 Substituted cyclohexanes occur widely in nature
 The cyclohexane ring is free of angle strain and
torsional strain
 The conformation is has alternating atoms in a
common plane and tetrahedral angles between all
carbons
 This is called a chair conformation

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How to Draw Cyclohexane

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2.10 Axial and Equatorial Bonds in Cyclohexane

 The chair conformation has two kinds of positions for

substituents on the ring: axial positions and
equatorial positions
 Chair cyclohexane has six axial hydrogens
perpendicular to the ring (parallel to the ring axis) and
six equatorial hydrogens near the plane of the ring

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Drawing the Axial and Equatorial Hydrogens

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2.11 Conformational Mobility of Cyclohexane
 Chair conformations readily interconvert,
resulting in the exchange of axial and
equatorial positions by a ring-flip

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Conformations of Monosubstituted Cyclohexanes
 Two conformations of monosubstituted cyclohexane aren’t
equally stable.
 The equatorial conformer of methyl cyclohexane is more
stable than the axial by 7.6 kJ/mol because of1,3-diaxial
steric interactions in axial conformation.

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Where Do Drugs Come From?

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