Alkyl Group

• Alkyl group contains one less hydrogen than the corresponding

alkane.
• In naming this group the “-ane” is dropped and “-yl” is added.
• For example, methane becomes methyl.
• Ethane becomes ethyl.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 2

Section 14.3
Alkyl Group
This group does not exist independently but occurs bonded to
another atom or molecule.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 3

Section 14.3
Constitutional Isomers
• Compounds that have the same molecular formula
but different structural formulas
• In the case of many alkanes there is more than one
way to arrange the atoms
• For example butane and isobutane
• Both of these alkanes have the molecular formula
of C4H10
• But their structural formula and arrangement is
quite different

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 4

Section 14.3
Butane
Continuous-Chain or Straight-Chain Structure
Structural
C4H10
Formula

Ball-and-Stick Model

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 5

Section 14.3
Isobutane (2-methylpropane)
Branched-chain Structure
Structural Formula C4H10

Ball-and-Stick
Model

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 6

Section 14.3
Constitutional Isomers
• Constitutional Isomers may exist whenever it is possible to construct a
different structural arrangement:
• Using the same number and types of atoms
• Without violating the octet rule
• In other words, the same atoms may be connected to one another in
different, but valid, ways.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 7

Section 14.3
Number of Possible Isomers of Alkanes
• Carbon Atoms can
bond in many
different ways

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 8

Section 14.3
Organic Compound Nomenclature
• Due to the large number, variety, and complexity
of organic compounds, a consistent method of
nomenclature has been developed.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 9

Section 14.3
IUPAC System of Nomenclature
For Alkanes
• Compound is named as a derivative of the longest
continuous chain of C atoms.
• Positions & names of the substituents added
• If necessary, substituents named alphabetically
• More than one of same type substituent – di, tri, tetra
• The C atoms on the main chain are numbered by
counting from the end of the chain nearest the
substituents.
• Each substituent must have a number.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 10

Section 14.3
An Example to Consider
• The longest continuous chain of C atoms is five
• Therefore this compound is a pentane derivative
with an attached methyl group
• Start numbering from end nearest the substituent
• The methyl group is in the #2 position
• The compound’s name is 2-methylpentane.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 11

Section 14.3
Substituents in Organic Compounds

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 12

Section 14.3
Drawing a Structure from a Name
An Example
• Draw the structural formula for 2,3-
dimethylhexane.
• Note that the end name is hexane .
• Draw a continuous chain of six carbon (C) atoms,
with four bonds around each.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 13

Section 14.3
Drawing a Structure from a Name
An Example (cont.)
• Number the C atoms from right to left.
• Attach a methyl group (CH3--) to carbon number 2
and number 3.
• Add necessary H atoms.
• 2,3-dimethylhexane

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 14

Section 14.3
Drawing a Structure from a Name
Confidence Exercise
• Draw the structural formula for 2,2,4-
trimethylpentane.
• Note that the end name is pentane .
• Draw a continuous chain of five carbon (C) atoms,
with four bonds around each.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 15

Section 14.3
Drawing a Structure from a Name
Confidence Exercise (cont.)

• Number the C atoms from right to left.

• Attach two methyl groups (CH3--) to carbon number
2 and one to number 4.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 16

Section 14.3
Drawing a Structure from a Name
Confidence Exercise (cont.)

• Add necessary H atoms.

• 2,2,4-trimethylpentane

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 17

Section 14.3
2,2,4-trimethylpentane
Ball-and-Stick Model

Copyright © Bobby H. Bammel. All rights reserved.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 18

Section 14.3
Cycloalkanes
• Members of the cycloalkane group possess rings of
carbon atoms.
• They have the general formula CnH2n.
• Each carbon atom is bonded to a total of four
carbon or hydrogen atoms.
• The smallest possible ring consists of
cyclopropane, C3H6.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 19

Section 14.3
The First Four Cycloalkanes

Note that in the condensed structural formulas, there is a carbon atom at each
corner and enough hydrogens are assumed to be attached to give a total of four
single bonds.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 20

Section 14.3
Drawing the Structure of a Cycloalkane
• Draw the geometric figure indicated by the compound’s name ,
“pentane.”

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 21

Section 14.3
Drawing the Structure of a Cycloalkane
• Place each substituent on the ring in the numbered position  “1
chloro-2-ethyl-”
• 1-chloro-2-ethylcyclopentane

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 22

Section 14.3
Alkenes
• Members of the alkene group have a double bond
between two carbon atoms.
• One hydrogen atom has been removed from two
adjacent carbon atoms, thereby allowing the two
adjacent carbon atoms to form a double bond.
• General formula is CnH2n
• Begins with ethene (ethylene)
• C2H4

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 23

Section 14.3
Some Members of the Alkene Series

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 24

Section 14.3
Naming Alkenes
• “-ane” suffix for the corresponding alkane is
changed to “-ene” for alkenes.
• A number preceding the name indicates the C
atom on which the double bond starts.
• The carbons are numbered such that the double bond
has the lowest number.
• For example, 1-butene and 2-butene

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 25

Section 14.3
Alkenes are very Reactive and are termed
“unsaturated hydrocarbons”
• Alkenes will characteristically react with hydrogen to form the corresponding
alkane.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 26

Section 14.3
Alkynes
• Members of the alkyne group have a triple bond
between two carbon atoms.
• Two hydrogen atoms have been removed from
each of two adjacent carbon atoms, thereby
allowing the two adjacent carbon atoms to form a
triple bond.
• General formula is CnH2n-2
• Begins with ethyne (acetylene)
• C2H2

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 27

Section 14.3
Some Members of the Alkyne Series

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 28

Section 14.3
Alkynes are Unsaturated Hydrocarbons
• Due to the triple carbon bond, each alkyne molecule can react with two molecules
of hydrogen.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 29

Section 14.3
Derivatives of Hydrocarbons
• Organic molecule characteristics depend on the
number, arrangement, and type of atoms.
• Functional Group – any atom, group of atoms, or
organization of bonds that determine specific
properties of a molecule
• Generally the functional group is the reactive part of
the molecule.
• Due to the functional group’s presence, certain
predictable properties ensue.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 30

Section 14.4
Derivatives of Hydrocarbons
• Examples of functional groups include:
• The double bond in alkenes & triple bond in alkynes.
• Cl atom, F atom, –OH group, methyl (CH3 –) group.
• Derivatives of hydrocarbons are organic compounds
that contain atoms other than C and H.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 31

Section 14.4
Alkyl Halides
• Alkyl halides have the general formula R—X, where
X is a halogen and R is an alkyl group
• CFC’s (chlorofluorocarbons) are examples of alkyl
halides.
• A well known CFC is dichlorodifluoromethane
(Freon-12)
• Extensively used in the past in cooling devices.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 32

Section 14.4
Alkyl Halides
• Another example of an alkyl halide is chloroform.
• In the past it was used as a surgical anesthetic but it is
now a known carcenogen.
• Carbon tetrachloride was also used extensively in
the past, until it was linked to liver damage.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 33

Section 14.4
Drawing Constitutional Isomers
An Example
• Draw the structural formulas for the two alkyl
halide isomers that have the molecular formula
C2H4Cl2.
• Recall that C atoms form four bonds, H & Cl form
one bond each.
• Draw a two-carbon backbone.
• Add enough bonds so that each C has four.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 34

Section 14.4
Drawing Constitutional Isomers
An Example (cont.)
• Note, there are just enough open bonds to attach the four H
and two Cl atoms.
• Fill in the Cl atoms in as many ways as possible.
• Remember that you are constrained by the tetrahedral
geometry (109.5o) of the four C bonds.

• Fill in the open bonds with H

atoms and name the
compounds.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 35

Section 14.4
Drawing Constitutional Isomers
Confidence Exercise
• Two constitutional isomers of C3H7F exist. Draw
the structure for each.
• Note that the formula ratio is that of an alkane.
• Draw a three-carbon backbone.
• Add enough bonds so that each C has four.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 36

Section 14.4
Drawing Constitutional Isomers
Confidence Exercise (cont.)
• Note, there are just enough open bonds to attach
the seven H and the one F atoms.
• Fill in the F atoms in as many ways as possible.
• Remember that you are constrained by the
tetrahedral geometry (109.5o) of the four C bonds.

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 37

Section 14.4
Drawing Constitutional Isomers
Confidence Exercise (cont.)
• Fill in the open bonds with H atoms and name the
compounds.

1-Fluoropropane 2-Fluoropropane

Copyright © Houghton Mifflin Company. All rights reserved. 14 | 38

Section 14.4