Ch.

13
Hydrocarbons

Milbank High School

Objectives
1. What is organic chemistry? In general, how do organic
compounds differ from inorganic compounds?
2. Why are there so many more organic compounds than
inorganic compounds?
3. What are hydrocarbons? What structural features identify
alkanes? Alkenes? Alkynes? Aromatic hydrocarbons?
4. How are alkanes, alkenes, alkynes, and aromatic hydrocarbons
named using IUPAC nomenclature?
5. What are the physical and chemical properties of alkanes,
alkenes, alkynes, and aromatic hydrocarbons?

Objectives
6. What is an alkyl group?
7. What are some products from reactions of alkanes?
How are they formed?
8. What are the major reactions of alkenes? What are
the products of those reactions?
9. What are polymers? How are they formed and
utilized?
10. What is petroleum and how is it utilized?

Organic Chemistry
Chemistry of compounds that contain
carbon
Combine mainly with hydrogen, oxygen, and
nitrogen
Over 10 million compounds made with these
4 elements

95% of compounds contain carbon

Form stable, covalent bonds with each other

Properties
Organic (Benzene)

Low melting pts

Low boiling pts
Low solubility in water
Highly flammable
Nonconductive
Covalent bonds

Inorganic (NaCl)

High melting pts

High boiling pts
Soluble in water
Nonflammable
Conductive
Ionic bonds

Hydrocarbons
Compounds containing only two elements
Carbon and hydrogen

Sec. 13.1
Alkanes: Structures and Names
Objectives
Identify an alkane
Determine what an isomer of an alkane is
Identify different types of alkanes

Alkanes
Saturated Hydrocarbons
Called saturated because each carbon is
bonded to four other atoms
Only single bonds
Methane
Ethane
Propane

Homology
Related compounds
Homologs
Have properties that vary in a regular and
predictable manner
A manner of organization
Similar to P.T.

Isomers
Different compounds having the same
molecular formula
Butane
Isobutane (isolated branched chain)

Isomers
Pentane
Isopentane
Neopentane

Alkanes
CnH2n+2
Representation
Structural Formulas
Condensed Structural Formulas
Butane

Alkyl Group
A group of atoms that results when one
hydrogen atom is removed from an alkane
CnH2n+1
Change ane ending to yl
Methyl
Ethyl
Propyl

Sec. 13.2
IUPAC Nomenclature
Define IUPAC
Examine the rules for IUPAC naming
Determine the correct names of alkanes

IUPAC Nomenclature
Geneva, Switzerland 1892
International Union of Pure and Applied
Chemistry
IUPAC System of Nomenclature
(isobutane, isopentane are common names)

IUPAC Rules
1. Name the longest chain in the parent
compound. End in ane. (Root name)
Number each carbon
See Example

2. Note the alkyl groups attached

3. Number the carbon that the group is
attached to.
Must use the lowest number possible.
See Example

IUPAC Rules Cont

4. Use prefixes to indicate the amount of
attached groups
See Example

5. If there are more than two or more

different substituents, list them in
alphabetical order. If at equal points,
lower alphabetical order given lowest
number
See Example

IUPAC Rules Cont

6. Prefixes not included in alphabetizing
See Example

Name each of the following

Name each of the following

A.

B.

C.

D.

Answers
a. 3-ethylhexane
b. 2,4-dimethylpentane
c. c. 3-methylhexane
d. 4-isopropylheptane

Draw the structural formulas for

each of the following
4-propylheptane
3-ethyl-2-methylpentane
3-isopropyl-3-methyloctane

Answers

Sec. 13.3
Properties of Alkanes
Objectives
Determine the physical and physiological
properties of alkanes

Physical Properties

Nonpolar
Insoluble in water

Less dense than water

Less than 1.0g/ml

Related to one another

See chart

Boiling points
Increase with higher molar mass

Physiological Properties
Gases serve as anesthetics
Liquid alkanes
Light liquids
Harmful to lungs
Heavy liquids
Mineral oil
Petroleum jelly

Sec. 13.4
Chemical Properties: Reactions
of Alkanes
Objectives
Determine the chemical properties of alkanes

Chemical Properties
Do not react with many laboratory agents
Usually very flammable
Undergo combustion reactions
CH4 + 2 O2 CO2 + 2 H2O + Heat
2 CH4 + 3 O2 2 CO + 4 H2O
(Harmful carbon monoxide reaction)

Sec. 13.5
Halogenated Hydrocarbons
Objectives
Define what halogenated hydrocarbons are
Name halogenated hydrocarbons using
common and IUPAC names

Halogenated Hydrocarbons
Have one or more hydrogen atoms
replaced by halogen atoms
Usually these are formed under UV light or
very high temps

Results in an alkyl halide

Common Names
First part of name is alkyl group
Second part is the halogen, ending in ide

Name these:
CH3CH2Br
(CH3)2CHCl
CH3I
CH3CH2CH2F

Answers

Ethyl bromide
Isopropyl chloride
Methyl iodide
Propyl flouride

IUPAC Names
Rules similar to those used for naming
alkanes
Substitute in the prefixes fluoro-, chloro-,
bromo-, and iodo-

Give the IUPAC name for each

of the following compounds

Answers

2-chloropentane
4-bromo-2-methylhexane
2-chloro-3-methylbutane
1-bromo-3-chloro-4-methylpentane

Sec. 13.6
Cycloalkanes
Define what a cycloalkane is
Name and draw cycloalkanes

Cycloalkanes
Carbon atoms that are joined in a ring or
circle
Simplest: cyclopropane

Another: cyclohexane

Naming
Add cyclo Otherwise fairly similar to regular naming

Draw structures for the following

compounds
Cyclooctane
Ethylcyclohexane
1,1,2-trimethylcyclobutane

Answers
A.

B.

C.

Draw these structures

Cyclopentane
1-ethyl-2-methylcyclopentane
1-ethyl-1,2,5,5-tetramethylcycloheptane

Answers
A.

B.

C.

Sec. 13.7
Alkenes
Objectives
Define alkene
Name alkenes using IUPAC rules

Alkenes
End in -ene
Unsaturated hydrocarbons

Have a double bond (CH3=CH2)

IUPAC Rules
1. Name the longest chain.
2. Indicate the position of the double bond
with the lowest number possible.
3. Substituent groups named like alkanes

5-methyl-2-hexene

Name each of the following

Answers

6-dimethyl-2-heptene
2-ethyl-1-butene
4-ethyl-2-methyl-2-hexene
1-methylcyclohexene
2,4,4-trimethyl-2-pentene

Draw the structure for the

following
3,4-dimethyl-2-pentene
3-ethyl-2-methyl-1-hexene
3-isopropylcyclopentene

Answers
A.

B.

C.

Sec. 13.8
Properties of Alkenes
Objectives
Determine the properties of alkenes

Properties of Alkenes
Similar to alkanes
Occur widely in nature
Ethylene
Triggers fruit ripening
Can be used artifically

Others
Carotene
Vitamin A

Fruit coloring

Sec. 13.9
Chemical Properties: Reactions
of Alkenes
Define addition reactions
Discuss hydrogenation and hydration
Write equations for reactions between
alkenes and other substances

Addition Reactions
One of the bonds in the double bond is broken
and each of the involved carbon atoms then
bonds to another atom or group

Hydrogenationaddition of hydrogen to an
unsaturated molecule

Halogen addition
Alkenes readily add halogen molecules

Hydration
Addition of water to an alkene

Equations
Write equations for the reaction between
CH3CH=CHCH3 and each of the following
H2
Br2
H2O (H2SO4 catalyst)

Answers

 Write equations for the reaction of

each of the following.
H2 (Ni catalyst)
Cl2
H2O (H2SO4 catalyst)

with

Answers

Sec. 13.11
Alkynes
Define alkyne
Name alkynes using IUPAC naming rules

Alkynes
Carbon atoms share 3 pairs of electrons,
forming a triple bond
Acetylene

Alkynes have similar properties to those of

alkanes and alkenes
Naming is the same, except they end in
-yne

Sec. 13.12
Benzene
Objectives
Recognize the versatile structure of a
benzene ring

Benzene
Recognized by Michael Faraday in 1825
Six sided structure with single and double
mobile bonds
Figure
Resonancea word
used to describe the
13.13
phenomenon in which no single Lewis
structure can be used

Sec. 13.13
Structure and Nomenclature of
Aromatic Compounds
Define and name aromatic hydrocarbons
and aliphatic compounds
Determine the difference between ortho,
meta, and para distribution

Aromatic Compounds
Benzene
Named because thought to have strong
aroma
Now define as anything that has a
benzene ring
Aliphatic compoundsnonaromatic

Naming
One substituenteasy

Naming
2 substituents2 different ways
One waysame as before
Other wayuses the terms ortho, meta,
and para
Ortho (1,2 distribution)
Meta (1,3 distribution)
Para (1,4 distribution)

Examples

Aryl Groups
Sometimes Benzene rings attach to
alkanes or alkenes
Known as aryl groups
Most common one is phenyl

Sec. 13.14
Uses of Benzene and Benzene
Derivatives
Objectives
Discuss some of the uses of benzene

Uses of Benzene

Most comes from petroleum

Used as a starting material
Added to fuels to improve octane rating
Cigarette smoke
Very toxic
In Nature..

Tryptophan
Vitamin K
Folic acid
Many drugsTable 13.12