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HYDROCARBONS
Reactions and Applications

Prepared by
Andrea D. Leonard
University of Louisiana at Lafayette

Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

Focus on the Environment

Combustion

SATURATED HYDROCARBONS
REACTIONS

AND APPLICATIONS

Alkanes have no functional group, so they undergo

few reactions.
Alkanes undergo Combustion reaction .
It is an oxidationreduction reaction.
In the combustion reaction, alkanes burn in the
presence of O2 gas to form CO2 and H2O.
The products, CO2 + H2O, are the same, regardless
of the identity of the alkane that undergoes
combustion.

Focus on the Environment

Combustion

Focus on the Environment

Combustion

If there is not enough O2 to react, incomplete

combustion may occur, and carbon monoxide (CO)
is formed instead of carbon dioxide (CO2).

Carbon monoxide is a poisonous gas that binds

to hemoglobin in blood, thereby reducing the
amount of O2 that can be transported to cells.

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Reactions of Alkenes

UNSATURATED
HYDROCARBONS
REACTIONS

Alkenes undergo addition reactions wherein new

groups X and Y are added to the alkene. One bond
of the double bond is broken and two new single
bonds are formed.

AND APPLICATIONS

Reactions of Alkenes

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Addition of HydrogenHydrogenation

TYPE OF REACTION

Hydrogenation is the addition of H2 to an alkene.

Hydrogenation
Halogenation
Hydrohalogenation
Hydration

The metal catalyst (usually palladiumPd) speeds

up the rate of the reaction.
The product of hydrogenation is an alkane.
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Reactions of Alkenes

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Reactions of Alkenes

Addition of HydrogenHydrogenation

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Addition of HalogenHalogenation
Halogenation is the addition of halogen (X2) to
an alkene.

Another example of hydrogenation:

X2 is usually Cl2 or Br2.

Halogenation occurs readily and does not require

a catalyst.
The product of halogenation is a dihalide.
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Reactions of Alkenes

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Reactions of Alkenes

Addition of HalogenHalogenation

Addition of Hydrogen Halides Hydrohalogenation

Additional examples of halogenation:

Hydrohalogenation is the addition of HX (HCl or

HBr) to an alkene.

The product of hydrohalogenation is an alkyl

halide.
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Reactions of Alkenes

Reactions of Alkenes

Addition of Hydrogen Halides Hydrohalogenation

Addition of Hydrogen Halides Hydrohalogenation

If the reactant is an asymmetrical alkene, two
possible products can be formed in theory.

Additional examples of hydrohalogenation:

These two potential products are constitutional

isomers.
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Reactions of Alkenes

Addition of Hydrogen Halides Hydrohalogenation

To determine which of the two products will
actually form, we use Markovnikovs rule.

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Reactions of Alkenes

Addition of Hydrogen Halides Hydrohalogenation

Looking at the reaction again:

Markovnikovs rule states that the H atom of HX

will bond to the less substituted C atom in the
CC double bond.
This means the C in the double bond with the
most Hs will bond to the H atom of HX.

C2 is bonded to 1 H
C1 is bonded to 2 Hs
C1 has more Hs, so it will bond to the H from HCl.
2-Chloropropane is the only product formed.

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Reactions of Alkenes

Reactions of Alkenes

Addition of WaterHydration

Addition of WaterHydration

Hydration is the addition of water to an alkene.

An additional example of hydration:

Hydration requires a strong acid, H2SO4.

The product formed by hydration is an alcohol.

Reactions of Alkenes

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Focus on Health and Medicine

Addition of WaterHydration

Margarine or Butter?

If the reactant is an asymmetrical alkene, the

product will be determined by Markovnikovs rule.
OH will bond here
this C has no Hs

CH3

CH3
+

OH

Butter is made up of saturated fatty acid chains.

H2SO4

OH
H

H
H

this C has 1 H

only product

H will bond here

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Focus on Health and Medicine

Margarine or Butter?

A diet rich in saturated fatty acids is widely

considered to be unhealthy.
Scientists have attempted to produce alternative
versions of butter (margarine) with similar taste
and properties, but with some CC double bonds
(i.e., unsaturated fatty acid chains).

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Focus on Health and Medicine

Margarine or Butter?

Most naturally occurring unsaturated fatty acid

compounds are liquids at room temperature.
To make the desired butter alternative, we need a
compound that is a solid at room temperature.
This is done by partially hydrogenating unsaturated
fatty acid compounds.
This process allows only a few CC double bonds
to remain on the chain, making a solid fatty acid
that is not naturally occurring.

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Focus on Health and Medicine

Margarine or Butter?

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Focus on Health and Medicine

Margarine or Butter?

Unfortunately, some partial hydrogenations leave

trans double bonds on the fatty acid chain.
Trans fatty acids are very similar in shape to
saturated fatty acids.
Trans fatty acids are widely considered to be
just as unhealthy as saturated fatty acids.
Nutritionists agree that a healthy diet consists of
very few saturated or trans fats.

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PolymersThe Fabric of Modern Society

Polymers are large molecules made up of
repeating units of smaller molecules (monomers)
covalently bonded together.

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PolymersThe Fabric of Modern Society

Synthetic Polymers

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PolymersThe Fabric of Modern Society

Synthetic Polymers

In polymerization, the monomer CC double bonds

are broken and single bonds linking the monomers
together are formed.

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Aromatic Compounds
Aromatic compounds are compounds that
contain a benzene ring.

Each C is trigonal planar (i.e., 120bond angles),

making benzene a planar molecule.

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Aromatic Compounds

Aromatic Compounds

In this hybrid structure, all three electron pairs in

the double bonds are delocalized in the sixmembered ring.

Aromatic hydrocarbons do not undergo the

addition reactions that characterize alkenes.

This can be drawn as a circle inside the hexagon.

Delocalization gives benzene added stability

compared to other unsaturated hydrocarbons.

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Nomenclature of Benzene Derivatives

Monosubstituted Benzenes

To name a benzene ring with one substituent:

name the substituent first

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Nomenclature of Benzene Derivatives

Monosubstituted Benzenes

Some monosubstituted benzenes have common

names that you must learn.

then add the word benzene at the end

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Nomenclature of Benzene Derivatives

Disubstituted Benzenes

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Nomenclature of Benzene Derivatives

Disubstituted Benzenes

If there are two groups on the benzene ring and

they are different, alphabetize the two substituent
names.

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Nomenclature of Benzene Derivatives

Disubstituted Benzenes

If one of the two substituents is part of a common

root, then name the molecule as a derivative of
that monosubstituted benzene.

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Nomenclature of Benzene Derivatives

Polysubstituted Benzenes

1. Number to give the lowest possible numbers

around the ring.
2. Alphabetize the substituent names.
3. When the substituents are part of common roots:
name the molecule as a derivative of that
monosubstituted benzene
put the common root substituent at C1, but omit
the 1 from the name

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Nomenclature of Benzene Derivatives

Polysubstituted Benzenes

Assign the lowest set of numbers.

Alphabetize the names of all the substituents.
4-chloro-1-ethyl-2-propylbenzene

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Nomenclature of Benzene Derivatives

Polysubstituted Benzenes

Name the molecule as a derivative of the common

root aniline.
Assign the NH2 group to position 1 and then assign
the lowest possible set of numbers to the other groups.
2,5-dichloroaniline

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Aromatic Compounds with More than

One Ring

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Reactions of Aromatic Compounds

Aromatic compounds undergo substitution
reactions primarily.
Substitution is a reaction in which an atom is
replaced by another atom or group of atoms.

Substitution of H by X keeps the stable aromatic

ring intact.

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Reactions of Aromatic Compounds

Chlorination and DDT

In chlorination, a Cl atom substitutes for a

hydrogen atom on the benzene ring.

The pesticide DDT is

formed by a chlorination
reaction.

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Focus on Health and Medicine

Nitration and Sulfa Drugs

Benzene reacts with nitric acid (HNO3) in the

presence of sulfuric acid (H2SO4) to form
nitrobenzene.

Substitution of a nitro group (NO2) for a hydrogen

is called nitration.

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Reactions of Aromatic Compounds

Sulfonation and Detergent Synthesis

In sulfonation, benzene reacts with SO3 in the

presence of H2SO4 such that a SO3H group
substitutes for a hydrogen atom on the benzene ring.

The synthetic detergent

shown is a product of
sulfonation.