ORGANIC CHEMISTRY

CHM 207

CHAPTER 3:
ALKENES

Nomenclature
Structures and
physical
properties

Subtopics

Addition

Preparation of
alkenes
Combustion
Reactions of
alkenes
Oxidation
Unsaturation
tests
Polimerization
Uses

ALKENES

Also called olefins

Contain at least one carbon-carbon double bond
(C=C)
General formula, CnH2n (n=2,3,)
Classified as unsaturated hydrocarbons
(compound with double or triple carbon-carbon
bonds that enable them to add hydrogen atoms.
sp2-hybridized
For example:
C2H4 - ethylene
CH2

CH2

RULE 1. Select the longest continuous carbon chain that

contains a double bond.

This chain
contains 6 C
atoms

This chain
contains 8
C atoms
wrong

correct

RULE 2. Name this compound as you would an alkane, but

change ane to ene for an alkene.
- The chain contain 8 C, therefore, name the parent
compound octene.

RULE 3. Number the carbon chain starting with the end

nearer to the double bond.
Use the smaller numbes on the double-bonded carbon to
indicate the position of the double bond. Place this number
in front of the alkene name.
This end of the chain is closest to the
double bond. Begin numbering here.
4

5
6
7
8

The name of the parent

compound is 1-octene.

RULE 4. Branched chains and other groups are treated as in

naming alkanes. Name the substituent group, and
designate its position on the parent chain with a number.

The ethyl group is attached to carbon 4.

5
6
7
8

4-ethyl-1-octene

Placing numbers (location of double bond) before the

part of the name ene.
Example:
1

CH2 C CH2
H

CH3

Old naming system: 1-butene

New naming system: but-1-ene

CH2 C
H

CH3 C
H

C CH2 CH2 CH3

H

Old naming system: 2-hexene

New naming system: hex-2-ene

CH3
3

C CH3
H

Old naming system: 3-methyl-1-butene

New naming system: 3-methylbut-1-ene

A compound with more than one double bond.

- Two double bond: diene
- Three double bond: triene
- Four double bond: tetraene
* Numbers are used to specify the locations of the double
bonds.

CH2

C
H

C CH2
H

CH3 C C
H H

IUPAC names: 1,3-butadiene

new IUPAC names: buta-1,3-diene
1

4
6

IUPAC names: 1,3, 5, 7-cyclooctatetraene

new IUPAC names: cycloocta-1,3,5,7-tetraene

C
H

C
H

C
H

1,3,5-heptatriene
hepta-1,3,5-triene

CH2

Alkenes names as substituents are called alkenyl

groups.
Can be named systematically as ethenyl, propenyl, etc.
or by common names such as vinyl, ally, methylene and
phenyl groups.

CH2
methylene group
(methylidene group)

-CH=CH2
vinyl group
(ethenyl group)

-CH2-CH=CH2
allyl group
(2-propenyl group)

CH=CH2
CH2 CHCHCH2CH CH2
3-methylenecyclohexene

IUPAC name: 3-vinyl-1,5-hexadiene

New IUPAC name: 3-vinylhexa-1,5-diene

Contains C=C in the ring

cyclopropene

cyclohexene

cyclobutene cyclopentene

Nomenclature of cycloalkenes:
- Similar to that alkenes
- Number the cycloalkane so that the double bond is between C1 and
C2 and so that the first substituent has as low a number as possible.
* Double bond always between C1 and C2.
6
5
4

1
2

CH3

3
1-methylcyclohexene

5
4

CH2CH3

1
3

1,5-dimethylcyclopentene

3
4

IUPAC name: 2-ethyl-1,3-cyclohexadiene

New IUPAC name: 2-ethylcyclohexa-1,3-diene

H3C
H

CH2CH3
H

cis-2-pentene

H3C
H

H
C

C
CH2CH3

trans-2-pentene

cis two particular atoms (or groups of atoms) are

adjacent to each other
trans the two atoms (or groups of atoms) are
across from each other

i) boiling points and densities

ii)polarity

i.

Boiling points and densities

- Most physical properties of alkenes are similar to those

alkanes.
- Example: the boiling points of 1-butene, cis-2-butene, trans-2butene and n-butane are close to 0oC.
- Densities of alkenes: around 0.6 or 0.7 g/cm3.
- Boiling points of alkenes increase smoothly with molecular
weight.
- Increased branching leads to greater volatility and lower
boiling points.

ii.

Polarity

- relatively nonpolar.
- insoluble in water but soluble in non-polar solvents such
as hexane, gasoline, halogenated solvents and ethers.
- slightly more polar than alkanes because:
i) electrons in the pi bond is more polarizable
(contributing to instantaneous dipole moments).
ii) the vinylic bonds tend to be slightly polar
(contributing to a permanent dipole moment).

Alkyl groups are electron donating toward double bond,

helping to stabilize it. This donating slightly polarizes the
vinylic bond, with small partial positive charge on the alkyl
group and a small negative charge on the double bond carbon
atom.
For example, propene has a small dipole moment of 0.35 D.
Vinylic bonds

H3C

H
C

H3C

CH3
C

H3C

H
C

propene, = 0.35 D Vector sum =

C
CH3

Vector sum = 0
propene, = 0.33 D propene, = 0
cis-2-butene, bp 4oC trans-2-butene, bp 1oC

In a cis-disubstituted alkene, the vector sum of the two dipole

moments is directed perpendicular to the double bond.

In a trans-disubstituted alkene, the two dipole moments tend to

cancel out. If an alkene is symmetrically trans-disubstituted, the
dipole moment is zero.

Cis- and trans-2-butene have similar van der Waals attractions, but
only cis isomer has dipole-dipole attractions.

Because of its increased intermolecular attractions, cis-2-butene

must be heated to a slightly higher temperature (4oC versus 1oC)
before it begins to boil.

H3C

H
C

H3C

CH3
C

H3C

H
C

Vector sum =
propene, = 0.33 D
cis-2-butene, bp 4oC

C
CH3

Vector sum = 0
propene, = 0
trans-2-butene, bp 1oC

i) dehydration of alcohols
ii) dehydrohalogenation of haloalkanes

Alkenes can be prepared in the following ways:

i.

Dehydration of alcohols

R-CH2-CH2-OH

ii.

conc. H2SO4

R-CH=CH2 + H2O

Dehydrohalogenation of haloalkanes

R-CH2-CH2-X

NaOH/ethanol
reflux

NaOH can be replaced by KOH

R-CH=CH2 + HX

Saytzeff rule:
- A reaction that produces an alkene would favour the
formation of an alkene that has the greatest number of
substituents attached to the C=C group.

Dehydration of alcohols
H+

CH3CH2-CH-CH3
OH

CH3CH2-CH=CH2 + H2O
1-butene

2-butanol

CH3CH=CH-CH3 + H2O
2-butene
major product

Dehydrohalogenation of haloalkanes
CH3CH-CH-CH2
H

Br H

2-bromobutane

KOH

alcohol
reflux

CH3CH=CH-CH3
2-butene
(major product)

CH3CH2CH=CH2
1-butene

Alkenes are more reactive than alkanes because:

i)

A carbon-carbon double bond consists of a and a bond. It is

easy to break the bond while the bond remains intact.

ii)

The electrons in the double bond act as a source of electrons

(Lewis base). Alkenes are reactive towards electrophiles which
are attracted to the negative charge of the electrons.

iii)

bond will broken, each carbon atom becomes an active site

which can form a new covalent bond with another atom. One
bond is converted into 2 bonds.

i) Addition reaction:
a) Addition of hydrogen (Catalytic hydrogenation)
b) Addition of halogens
- In inert solvent
- In water / aqueous medium
c) Addition of hydrogen halides
d) Addition reaction with concentrated sulfuric acid: hydration of
alkenes
e) Addition reaction with acidified water (H3O+): hydration of alkenes
ii) Combustion of alkenes
iii) Oxidation:
a) Epoxidation
b) Hydroxylation
c) Ozonolysis
iv) Polymerization

i) Addition reaction
a)

Addition of hydrogen (Catalytic hydrogenation):

- hydrogenation: addition of H to a double bond and triple bond to
yield saturated product.
- alkenes will combine with hydrogen in the present to catalyst to
form alkanes.

C C

H H

Pt or Pd
o

25-90 C

C C
H H

- Plantinum (Pt) and palladium (Pd) Catalysts

- Pt and Pd: temperature 25-90oC
- Nickel can also used as a catalyst, but a higher temperature of 140oC
200oC is needed.

EXAMPLES:
H2C CH2
ethylene

CH3CH2CH2CH2CH CH2
hexene

H2

H2

Pt
low pressure

Pt
low pressure

H3C CH3
ethane

CH3CH2CH2CH2CH2CH3
hexane

b) Addition of halogens:
i) In inert solvent:
- alkenes react with halogens at room temperature and in dark.
- the halogens is usually dissolved in an inert solvent such as
dichloromethane (CH2Cl2) and tetrachloromethane (CCl4).
- Iodine will not react with alkenes because it is less reactive than
chlorine and bromine.
- Fluorine is very reactive. The reaction will produced explosion.

C C

X X

inert solvent

X X = halogen such as Br2 or Cl2

Inert solvent = CCl4 or CH2Cl2

C C
X X

EXAMPLES:
H H
H C C H

H H
H C C H
Br Br

inert solvent (CCl4)

Br Br

ethene

1,2-dibromoethane
* the red-brown colour of the bromine solution will fade and the
solution becomes colourless.

Br2

CCl4

Br
1,2-dibromocyclohexane

cyclohexene
CH3CH=CH2
propene

Br

Cl2

CCl4

Cl Cl
CH3CH CH2
1,2-dichloropropane

b) Addition of halogens:
ii) In water / aqueous medium:
- chlorine dissolves in water to form HCl and chloric (l) acid
(HOCl).
Cl2 (aq) + H2O(l)
HCl(aq) + HOCl (aq)
- same as bromine
Br2 (aq) + H2O(l)

HBr(aq) + HOBr(aq)

* Reaction of alkenes with halogens in water/ aqueous solution (eg.

chlorine water and bromine water) produced halohydrins (an alcohol
with a halogen on the adjacent carbon atom).

EXAMPLES:
CH3CH=CH2 +

Br2

H2O

propene

CH3 CH CH2
CH3 CH CH2
Br Br
OH Br
1-bromo-2-propanol 1,2-dibromopropane
(major product)
(minor product)

* Br atom attached to the carbon atom of the double bond which has the greater
number of hydrogen atoms.
CH3CH2CH=CH2
1-butene

Cl2, H2O

CH3 CH2 CH CH2

OH Cl
1-chloro-2-butanol

c) Addition of hydrogen halides:

- Addition reaction with electrophilic reagents.
- Alkenes react with hydrogen halides (in gaseous state or in aqueous
solution) to form addition products.
- The hydrogen and halogen atoms add across the double bond to
form haloalkanes (alkyl halides).
- General equation:

C C
alkene

H X
C C

HX

haloalkane

- Reactivity of hydrogen halides : HF < HCl < HBr < HI

* Reaction with HCl needs a catalyst such as AlCl3

H2C CH2

HCl

AlCl3

CH3CH2Cl

EXAMPLES:

H-I
cyclopentene

CH3CH=CHCH3 + H-Br
2-butene

I
iodocyclopentane

Br
CH3CH2CHCH3
2-bromobutane

There are 2 possible products when hydrogen halides react with an

unsymmetrical alkene.
It is because hydrogen halide molecule can add to the C=C bond in
two different ways.
H H
CH3 C C H

H H
H-I

CH3 C C H
H I
1-iodopropane

H H
CH3 C C H

H H
H-I

CH3 C C H
I H
2-iodopropane
(major product)

Markovnikovs rules:
- the addition of HX to an unsymmetrical alkene,
the hydrogen atom adds to the carbon atom (of
the double bond) that already has the greater
number of hydrogen atoms.

Mechanism of electrophilic addition reactions:

- C=C : electron rich part of the alkene molecule
- Electrophiles: electron-seeking
Step 1: Formation of carbocation.
Attack of the pi bond on the electrophile to form carbocation.
+

C C

C C

Y-

E
carbocation
Step 2: Rapid reaction with a negative ion.
The negative ion (Y-) acts as nucleophile and attacks the positively
charged carbon atom to give product of the addition reaction.

C C
E

Y-

C C
E Y

CH3CHCH2
1
2
CH3CH=CH2

HCl

H Cl
1-chloropropane

Propene
CH3CHCH2
Cl H
2-chloropropane
(major product)
according to Markovnikov's
rules

MECHANISM:
Step 1: Formation of carbocation
H H H

H H
CH3 C C H

H Cl

H H H

H C C C H or H C C C H
H
H
H H
less stable carbocation
(1o carbocation)

Cl-

more stable carbocation

(2o carbocation)

- 2o carbocation is more stable than 1o carbocation.

- 2o carbocation tends to persist longer, making it more likely to combine with
Cl- ion to form 2-chloromethane (basis of Markovnikov's rule).

Step 2: Rapid reaction with a negative ion

H H H
H C C C H
H
H

H H H
Cl-

H C C C H
H Cl H
2-chloromethane (major product)

d)

Addition reaction with concentrated sulfuric acid: hydration of

alkenes
- the alkene is absorbed slowly when it passed through
concentrated sulfuric acid in the cold (0-15oC).
- involves the addition of H atom and HSO4 group across the
carbon-carbon double bond.
- follows Markovnikovs rule.

H H
H C C H

H H
H OSO3H
(H2SO4)

H C C H
H OSO3H
ethyl hydrogensulphate
(CH3CH2HSO4)

When the reaction mixture is added to water and warmed,

ethyl hydrogensulphate is readily hydrolysed to ethanol
CH3CH2OSO3H + H-OH

CH3CH2OH + H2SO4

(H2O)

*ethene reacts with concentrated H2SO4 to form ethanol*

or
*alkene reacts with concentrated H2SO4 to form alcohol*

e) Addition reaction with acidified water (H3O+): hydration of alkenes

Hydration: The addition of H atoms and OH groups from water
molecules to a multiple bond.
Reverse of the dehydration reaction.
Direct hydration of ethene:
- passing a mixture of ethene and steam over phosphoric (v) acid
(H3PO4) absorbed on silica pellets at 300oC and a pressure of 60
atmospheres.
- H3PO4 is a catalyst.
CH2=CH2 (g)

H2O (g)

ethene

C C
alkene

H3PO4
o

300 C, 60 atm

H2O

H+

CH3CH2OH (g)
ethanol

H OH
C C
alcohol

Markovnikovs rule is apply to the addition of a water molecule

across the double bond of an unsymmetrical alkene.
For examples:

CH3
CH3 C

CH2

CH3

H
25oC

H OH

CH3 C

2-methylpropene

CH2

OH H
tert-butyl alcohol

CH3CHCH3

CH3CH=CH2 + H2O
propene

H+

OH
2-propanol

H+ = catalyst

MECHANISM OF ACID CATALYSED HYDRATION OF ALKENES

Step 1: Protonation to form carbocation
H H
CH3 C C H

H H H
H+

H C C C H
H
H
more stable carbocation
(2o carbocation)

Step 2: Addition of H2O to form a protonated alcohol

H H H
H C C C H
H
H

CH3CHCH3

O H
H

Step 3: Loss of a proton (deprotonated) to form alcohol

CH3CHCH3
O H
H

CH3CHCH3
OH

H+ = catalyst

ANTI-MARKOVNIKOVS RULE: FREE RADICAL

ADDITION OF HYDROGEN BROMIDE

When HBr is added to an alkene in the absence of peroxides it obey

Markovnikovs rule.

When HBr (not HCl or HI) reacts with unsymmetrical alkene in the
presence of peroxides (compounds containing the O-O group) or
oxygen, HBr adds in the opposite direction to that predicted by
Markovnikovs rule.

The product between propene and HBr under these conditions is 1bromopropane and not 2-bromopropane.

CH3CH=CH2

HBr

peroxide

CH3CH2CH2Br
1-bromopropane
(major product)
anti-Markovnikov's orientation

Anti-Markovnikovs addition:
- peroxide-catalysed addition of HBr occurs through a
free radical addition rather than a polar electrophilic
addition.
- also observed for the reaction between HBr and
many different alkenes.
- not observed with HF, HCl or HI.

Alkenes goes to hydroboration reaction to form antiMarkovnikov alcohol.

H2O2, -OH

B2H6

C C

C C
H OH
anti-markovnikov

examples:

CH3CH=CH2

H2O2, -OH

B 2H 6

propene

CH3
CH3 C CH2

CH3CHCH2-OH
propanol

B 2H 6

H2O2, -OH

CH3 CH CH2 OH
isobutyl alcohol

isobutylene

CH3

CH3 CH C CH3
2-methyl-2-butene

CH3

B2H6

H2O2, -OH

CH3
CH3CHCHCH3
OH
3-methyl-2-butanol

ii) Combustion of alkenes

The alkenes are highly flammable and burn readily
in air, forming carbon dioxide and water.
For example, ethene burns as follows :
C2H4 + 3O2 2CO2 + 2H2O

iii) Oxidation

Oxidation: reactions that form carbon-oxygen bonds.

Oxidation reaction of alkenes:
a) Epoxidation
b) Hydroxylation
c) Ozonolysis

a) Epoxidation of alkenes

Epoxide / oxirane: a three-membered cyclic ether.

O
C C

R C

alkene

O
C C

O O H

peroxyacid

O
R C OH

epoxide (oxirane)

acid

Examples of epoxidizing reagent:

O
CH3 C O O H
peroxyacetic acid

O
C O OH
peroxybenzoic acid
(PhCO3H)

O
Cl

H
O

m-chloroperoxybenzoic acid
(MCPBA)

MCPBA
o

CH2CI2, 25 C
cyclohexene

1,2-epoxycyclohexane

MCPBA
o

CH2CI2, 25 C
cycloheptene

1,2-epoxycycloheptane

b) Hydroxylation of alkenes

Hydroxylation:
- Converting an alkene to a glycol requires adding a hydroxyl
group to each end of the double bond.
Hydroxylation reagents:
i) Osmium tetroxide (OsO4)
ii)Potassium permanganate (KMnO4)

C C

OsO4

H2O2

(or KMnO4, -OH)

OH OH
glycol

CH2 CH2

KMnO4 (aq), OHcold, dilute

ethene

CH2 CH2

MnO2

OH OH
1,2-ethanediol

KMnO4 (aq), OHCH3 CH CH2

cold, dilute
propene

CH3 CH CH2
OH OH
1,2-propanediol

* Also known as Baeyers test

MnO2

c) Ozonolysis of alkenes

Ozonolysis:

- The reaction of alkenes with ozone (O3) to form an ozonide, followed by

hydrolysis of the ozonide to produce aldehydes and /or ketone.
- Widely used to determine the position of the carbon-carbon double bond.
- Ozonolysis is milder and both ketone and aldehydes can be recovered
without further oxidation.

R'
O3

C C
R

R'

(CH3)2S

C C
R O O H or H2O, Zn/H+
ozonide

R'
C O

R
ketone

O C
H
aldehyde

i) O3
ii) (CH3)2S

3-nonene

CH3O
H

OCH3
H

i) O3
ii) (CH3)2S

H
O
CH3O

H
OCH3

O
O

O
O

iv) Polymerization of alkenes

Polymer: A large molecule composed of many smaller repeating units

(the monomers) bonded together.

Alkenes serves as monomers for some of the most common polymers

such as polyethylene (polyethene), polypropylene, polystyrene,
poly(vinyl chloride) and etc.

Undergo addition polymerization /chain-growth polymer:

- a polymer that results from the rapid addition of one molecule at a
time to a growing polymer chain, usually with a reactive intermediate
(cation, radical or anion) at the growing end of the chain.
repeating unit

CI

H
vinyl chloride

CI
C C

C C

C C
H

CI

CI H

Cl H

Cl

n
poly(vinyl chloride)

POLYMER
Polyethylene

Polypropylene

POLYMER USES

MONOMER
FORMULA

Bottles, bags,
films

Plastics, olefin
fibers

CH2=CH2
H

CH3
C

H
Polystyrene

Plastics, foam
insulation

Specialized
rubbers

CH2 CH2 n

CH3
CH2 CH n

H
C C

Poly(isobutylene)

POLYMER
REPEATING UNIT

CH3

C C

CH3

H2C C
H

CH3
CH2 C
CH3

i) Reactions of alkenes with KMnO4

ii) Reactions of alkenes with bromine.

UNSATURATION TESTS FOR ALKENES

i) Reaction of alkenes with KMnO4
- KMnO4 is a strong oxidizing agent.
- alkenes undergo oxidation reactions with KMnO4
solution under two conditions:
a) Mild oxidation conditions using cold, dilute,
alkaline KMnO4 (Baeyers test).
b) Vigorous oxidation conditions using hot,
acidified KMnO4.

a)

Reaction of alkenes with cold, dilute, alkaline KMnO4 (Baeyers

test)
- the purple colour of KMnO4 solution disappears and a cloudy
brown colour appears caused by the precipitation of manganese
(IV) oxide, MnO2.
- test for carbon-carbon double or triple bonds.
- a diol is formed (containing two hydroxyl groups on adjacent
carbon atoms).

K M n O 4 (aq), O H
co ld, d ilute

OH OH
a diol

M nO2

ii) Reaction of alkenes with bromine

- A solution of bromine in inert solvent (CH2CI2 or CCI4) and dilute
bromine water are yellow in colour.
- The solution is decolorised when added to alkenes or organic
compounds containing C=C bonds.

C C

C C

Br 2

CH 2CI 2

Br 2(aq)

H 2O

Br

Br

OH Br

Br

Br

DETERMINATION OF THE POSITION OF THE

DOUBLE BOND
a) Ozonolysis of alkenes:
- For example, ozonolysis of an alkene produces
methanal and propanone.
CH3

H
H C O
methanal

C CH3

propanone

remove the oxygen atoms from the carbonyl compounds and

joining the carbon atoms with a double bond.

H
H C

CH3
C CH3

CH3

C CH3

2-methylpropene

b) Reaction of alkenes with hot, acidified KMnO4

- by using hot, acidified KMnO4, the diol obtained is
oxidised further.
- cleavage of carbon-carbon bonds occurs and the final
products are ketones, carboxylic acids or CO2.
CH3
CH3 C CH2
2-methylpropene

KMnO4/H+

CH3
CH3 C O
propanone
(ketone)

CO2

+ H2O

Example:
An alkene with the molecular formula C6H12 is oxidised with hot
KMnO4 solution. The carboxylic acids, butanoic acid
(CH3CH2CH2COOH) and ethanoic acid (CH3COOH), are produced.
Identify the structural formula of the alkene.

i) cleavage of the double bond gives a mixture of carboxylic acids

H H
R C C R'

KMnO4/H

OH

OH
R C

O C R'

ii) location of the double bond is done by taking away the oxygen atoms from the
carboxylic acids and then joining the carbon atoms by the double bond.
RCOOH and R'COOH

RCH=CHR'

CH3CH2CH2COOH and CH3COOH

butanoic acid
ethanoic acid

CH3CH2CH2CH=CHCH3
2-hexene

R'
C C

R''

R''
H

R'
C O

O C

R''

OH
ketone

C C H
OH OH

R
R''

R R'

KMnO4/H+

R'
C O

O C
H
aldehyde

ketone

acid
+

R CH=CH2

KMnO4/H

R COOH + CO2 + H2O

Example:
+

KMnO4/H

C
4-methyl-4-octene

2-pentanone

HO

O
butanoic acid

i) PE
ii) PVC
iii) ethanol

USES OF ALKENES

Ethylene and propylene are the largest-volume industrial organic

chemicals.
Used to synthesis a wide variety of useful compounds.
H H
H H

CH2

ethylene oxide
H+
H2O

CH2 CH2
OH

OH

ethylene glycol

CH3 C OH

acetaldehyde

polymerize

H2C

oxidize

CH3 C

polyethylene

C C

acetic acid

oxidize

O2

Ag catalyst

H
C C
ethylene

Cl2

CH2 CH2
CI CI
ethylene dichloride

H2O
catalyst

CH3 CH2
OH
ethanol

NaOH

H
H C

CI
C H

vinyl chloride

i) POLYETHENE (PE)

The most popular plastic.

Uses:
i) Grocery bags
ii)Shampoo bottles
iii)Children's toy
iv)Bullet proof vests
v)Film wrapping
vi)Kitchenware

ii) POLYVINYL CHLORIDE (PVC)

H H
H C C CI
vinyl chloride

polymerize

H
C
H

CI H
C C
H H

CI H
C
C
H n H

CI
C
H

poly(vinyl chloride)
PVC, "vinyl"

USES OF PVC:
Clothing
- PVC fabric has a sheen to it and is waterproof.
- coats, shoes, jackets, aprons and bags.
As the insulation on electric wires.
Producing pipes for various municipal and industrial applications.
For examples, for drinking water distribution and wastewater mains.
As a composite for the production of accessories or housings for
portable electronics.
used in the building industry as a low-maintenance material.
Ceiling tiles.

USE OF ETHANOL:
Motor fuel and fuel additive.
As a fuel to power Direct-ethanol fuel cells (DEFC) in order to produce
electricity.
As fuel in bipropellant rocket vehicles.
In alcoholic beverages.
An important industrial ingredient and use as a base chemical for other
organic compounds include ethyl halides, ethyl esters, diethyl ether,
acetic acid, ethyl amines and to a lesser extent butadiene.
Antiseptic use.
An antidote.
Ethanol is easily miscible in water and is a good solvent. Ethanol is less
polar than water and is used in perfumes, paints and tinctures.
Ethanol is also used in design and sketch art markers.
Ethanol is also found in certain kinds of deodorants.