Functional Groups with:

Multiple Carbon–Carbon 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
Alkenes and Alkynes
 Alkenes contain a
double bond
between adjacent
carbon atoms.

 Alkynes contain a
triple bond.
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2
 Functional Groups with:
Carbon Singly Bonded to an Electronegative Atom
 Alcohols and Ethers
 An alcohol contains
the hydroxyl (-OH)
functional group.

 In an ether, an oxygen
atom is bonded to two
carbon atoms
–C–O–C– .

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 Functional Groups with:
Carbon–Oxygen Double Bond (Carbonyl Groups)
 Aldehydes and Ketones
 An aldehyde contains a
carbonyl group (C=O),
which is a carbon atom
with a double bond to an
oxygen atom, attached to
at least one hydrogen.

 In a ketone, the carbon of

the carbonyl group is
attached to two other
carbon atoms.
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6
 Carboxylic Acids and Esters

 Carboxylic acids contain the

carboxyl group, which is a
carbonyl group attached to a
hydroxyl group.
O

— C—OH
 An ester contains the carboxyl
group between carbon atoms.

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Publishing as Benjamin Cummings
7
Amines and Amides
 In amines, the functional
group is a nitrogen atom.
|
—N —

 In amides, the hydroxyl

group of a carboxylic acid
is replaced by a nitrogen
group.

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Summary of Functional Groups

9
Survey of Functional Groups

10
Survey of Functional Groups

11
Functional Groups in Everyday
Items

Methyl amine (fish)

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12
 Learning Check
Classify each of the following as alcohol, ether, aldehyde,
ketone, carboxylic acid, ester, or amine.
1) CH3–CH2–CH2–OH
2) CH3–O–CH2–CH3

3) CH3–CH2–NH2

O O
|| ||
4) CH3–C–OH 5) CH3–C–O–CH3

13
 Solution
Classify each of the following as alcohol, ether, aldehyde,
ketone, carboxylic acid, ester, or amine.
1) CH3─CH2─CH2─OH 2) CH3─O─CH2─CH3
alcohol ether
3) CH3─CH2─NH2 amine
O O
|| ||
4) CH3─C─OH 5) CH3─C─O─CH3
carboxylic acid ester

14
What functional group is not present in the naturally
occurring compound shown below?
OH O
20% 20% 20% 20% 20%
H3C OH
NH2

1. carboxylic acid
2. amine
3. primary alcohol
4. secondary alcohol
5. methyl group

1 2 3 4 5
3.2 Alkanes and Alkane 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

16
17
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)

18
Expanded and Condensed Structures

19
 Some Structures for Butane

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20
 Line-Bond Formulas
 Because each C atom has a tetrahedral
arrangement, the order of atoms is not a straight
line, but a zigzag pattern.
 A line-bond formula abbreviates the carbon
atoms and shows only the zigzag pattern of
bonds from carbon atom to carbon atom.

21
Hexane has Six Carbon Atoms
Hexane
 Is an alkane with 6 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

22
 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?

23
 Solution
A. CH3CH2CH2CH2CH3

B. C5H12

C. pentane

24
 Learning Check
Write the condensed structural formula for

A. ethane

B. heptane

25
 Solution
Write the condensed structural formula for

A. ethane CH3─CH3

B. heptane
CH3─CH2─CH2─CH2─CH2─CH2─CH3

26
 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
27
 Constitutional Isomers
 Isomers that differ in how their atoms are arranged in
chains are called constitutional isomers
 Compounds other than alkanes can be constitutional
isomers of one another
 They must have the same molecular formula to be isomers

28
Isomers of Butane
Isomers
 Have the same
molecular formula.
 Have different atom
arrangements. branch

 Of butane (C4H10)
consist of a straight
chain and a branched
chain each with 4
carbon atoms.

29
 3.4 Naming Alkanes
 Compounds are given systematic names by a process that
uses

 Follows specific rules

◦ Find parent hydrocarbon chain
◦ Carbons in that main chain are numbered in sequence
◦ Substituents are identified numbered
◦ Write compound name is single word
◦ Name a complex substituents as though it were a
compound itself
33
IUPAC Names for Simple Alkanes
•Use a prefix to indicate the number of carbons in a chain.
•End in –ane.

34
 Learning Check
A. Give the name of each compound:
1) CH3—CH3
2) CH3—CH2—CH3
3) CH3—CH2—CH2—CH2—CH2—CH3

B. Write the condensed structural formula of

pentane.

35
 Solution
A. Give the name of each compound:
1) CH3—CH3 ethane
2) CH3—CH2—CH3 propane
3) CH3—CH2—CH2—CH2—CH2—CH3
hexane
B. Write the condensed structural formula of
pentane.
CH3—CH2—CH2—CH2—CH3

36
 3.3 Alkyl Groups
 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
37
38
 Types of Alkyl groups
 Classified by the connection site (See Figure 3.3)
◦ 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)

39
Naming Substituents
IUPAC Common
CH3
methyl methyl
CH2 CH3 ethyl ethyl
CH2 CH2 CH3 propyl n-propyl

CH3
1-methylethyl Isopropyl
CH
CH3
CH2 CH2 CH2 CH3 butyl n-butyl
CH3
CH CH2 CH3 1-methylpropyl sec-butyl

CH3
CH2 CH CH3 2-methylpropyl Isobutyl
CH3
C CH3 1,1-dimethylethyl tert-butyl or
t-butyl
CH3
40
Naming Substituents
IUPAC Common
CH2 CH2 CH2 CH2 CH3 pentyl n-pentyl or
amyl
CH3
CH CH2 CH2 CH3 1-methylbutyl sec-pentyl
CH3
CH2 CH2 CH CH3 isopentyl or
3-methylbutyl isoamyl or i-amyl
CH3
C CH2 CH3
CH3 1,1- tert-pentyl or
dimethylpropyl tert-amyl or t-amyl
CH3
CH2 C CH3 2,2- neopentyl
dimethylpropyl
CH3

41
Naming Substituents
IUPAC

F Fluoro

Cl Chloro

Br Bromo

I Iodo

OH Hydroxy

42
 Alkanes with Alkyl Groups
CH3 methylpropane

CH3 CH CH3
methyl groups

CH3 CH3
CH3 CH CH2 CH CH3
2,4-dimethylpentane

43
 Learning Check

Write three isomers of C5H12 and name

each.

44
 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
45
 What is the best IUPAC name for the following
compound?
20% 20% 20% 20% 20%

1. 2-ethyl-3-isopropylhexane
2. 1-isopropyl-3-ethylhexane
3. 4-isopropyl-5-ethylhexane
4. 3-methyl-4-isopropylheptane
5. 4-isopropyl-3-methylheptane

1 2 3 4 5
 What is the name of the alkane shown below?

20% 20% 20% 20% 20%

1. 3,7-dimethyl-4-propyloctane
2. 2-methyl-5-(1-
methylpropyl)octane
3. 2-ethyl-6-methyl-3-
propylheptane
4. 3-methyl-4-(3-
methylbutyl)heptane
5. 2,6-dimethyl-5-propyloctane

1 2 3 4 5
Which of the following is not an isomer of
hexane?
20% 20% 20% 20% 20%
1. 2,2-dimethylbutane
2. 2,2-dimethylpentane
3. 3-methylpentane
4. 2-methylpentane
5. 2,3-dimethylbutane

1 2 3 4 5
Evaluation: By pair

Think-Pair-Share
Look a partner. You will be given 5
minutes to discuss the assigned
problem on the nomenclature of
alkanes and its cyclic analog.
Thank

•You
REACTIONS OF ALKANES
Review Questions
 What are the characteristics of alkanes?
 What are the two types of alkanes?
 In terms of general formula, how would
you differentiate cyclic alkanes from
acyclic alkanes?
 How are alkanes named?
REACTIONS OF ALKANES
An image of an oil spill…

Crude oil that leaks into the sea.

REACTIONS OF ALKANES
1. What happen when an oil tanker rupture
into the sea?
2. What will happen to the oil?
3. Does the oil that leaks into the sea forms
a layer on the surface?
4. Describe the layer that that forms on
the surface.
5. Why is there a formation such layer?
REACTIONS OF ALKANES
 Alkanes: water insoluble
less dense than water
Therefore, crude petroleum spilled
into the sea from a ruptured oil tanker
creates an insoluble oil slick on the
surface.
• The insoluble hydrocarbon oil poses a
special threat to birds.
REACTIONS OF ALKANES
Why insoluble hydrocarbon oil poses a
special threat to birds?
- Birds feathers are coated with natural
nonpolar oils for insulations.
- Birds lose their layer of natural
protection and may die.
 Properties of Alkanes
 contain only C-C and C-H bonds,
so they exhibit only weak
intermolecular forces.
 low melting point and boiling
point.
 low molecular weight alkanes are
gases at room temperature.
 alkanes used in gasoline are all
liquids.
57
Crude Oil
The hydrocarbons
in crude oil are
 Separated by
boiling points.
 Heated to
higher
temperatures to
produce gases
that can be
removed and
cooled.

58
 Properties of Alkanes

CH3(CH2)2CH3

Bp= -0.5 °C
CH3(CH2)3CH3 CH3(CH2)4CH3

Bp= 36 °C Bp= 69°C

Properties of Alkanes
 How would you describe the boiling point
of alkanes?
The melting and boiling point of alkanes
increase as the number of carbons
increases.
Increased surface area increases the
force of attraction between molecules.
REACTIONS OF ALKANES
 Alkanes are low affinity compounds
because they do not react as most
chemicals.

 They will burn in a flame, producing

carbon dioxide, water, and heat.
 REACTIONS OF ALKANES

1. Combustion
chemical reaction between
substance and oxygen that
proceeds with the
evolution of heat and light
Combustion of Alkanes
Alkanes
 Undergo combustion
by reacting with
oxygen to produce
carbon dioxide, water,
and energy.
 Are typically not very
reactive due to strong
C-C single bonds. Copyright © 2007 by Pearson Education, Inc.
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alkane + O2 CO2 + H2O + energy

63
Combustion of Alkanes
 Combustion of alkanes in the
form of natural gas, gasoline
or heating oil releases energy
for heating homes,
powering vehicles and co
 cooking food.
 Learning Check

Propane is used to provide heat for

cooking or warming a room. Write a
balanced equation for the complete
combustion of propane.

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65
Propane is used to provide heat
for cooking or warming a
room. Write a balanced
equation for the complete
combustion of propane.

Solution
C3H8 + 5O2 3CO2 + 4H2O + Energy

66
 REACTIONS OF ALKANES

2. Halogenation
chemical reaction between
substance and light that
proceeds with alkyl halide
and an acid
 Properties of Alkanes
 They react with Halogens like Cl2 in the
presence of light to replace H’s with Cl’s
(not controlled)

70
 Learning Check

Give the structures and names of the

possible monosubstituted products for
the reaction of propane with bromine in
the presence of light.

71
 Solution
Give the structures and names of the possible
monosubstituted products for the reaction of
propane with bromine in the presence of light.
CH3—CH2—CH2— Br
bromopropane; propyl bromide
Br
|
CH3—CH—CH3
2-bromopropane; isopropyl bromide
72
 Dyad Activity
Write a balanced equation for the
reaction for the complete combustion
and halogenation reaction of the
following compounds
1. Glucose
2. Octane
3. Monofluorination of butane
73
Assignment
 In a short bond paper
 Handwritten
 Research on the IUPAC rules in naming
alkenes and alkynes