Consumer Chemistry

Quarter
1
Module 3- Alkenes and
Cycloalkenes
 Welcome to Module 3:
Alkenes and Cycloalkenes

In this module we are going to study the following lessons:

1. Define alkenes
2. Name alkenes given the structural formula, molecular formula and
line angle formula
3. Draw/ Write the structure of alkenes
4. List down some practical applications of alkenes
Lesson 1: Hydrocarbon: Alkenes
• In organic chemistry, an alkene is an unsaturated hydrocarbon that contains a carbon–
carbon double bond.

• They are also sometimes referred to as olefins or as unsaturated compounds. They called
unsaturated because the C atoms in a C=C double bond don’t have as many hydrogens
bonded to them as an alkane does. Molecules with one double bond are called
monounsaturated. Molecules with multiple double bonds are called polyunsaturated. In
contrast, alkane molecules with no double bonds are saturated.

• The general formula for the alkenes is C nH 2n, where n is the number of carbon atoms in
the molecule. Decene is an alkene.
Physical Properties of Alkenes
 Physical State. These double-bonded compounds are
colourless and odourless in nature.
 Solubility. The alkenes are insoluble in water due to their
nonpolar characteristics.
 Boiling Point. The boiling points of the compounds increase
as the number of carbon atoms in the compound increases. ...

Chemical properties of alkenes

 Alkenes are chemically more reactive than alkanes. This is
because alkenes are unsaturated hydrocarbons that have a
double bond, C=C, between two carbon atom.
 Almost all of the chemical reactions of alkene occur at the
double bond.
Uses or applications of alkenes.
 Many alkenes can be polymerized, forming plastics.
 Ethylene is used to ripen fruit.
 The various forms of vitamin A (including beta-carotene) are alkenes, as is lycopene, an
antioxidant found in tomatoes.
 Some alkenes such as alpha-pinene and limonene smell good (and aren’t too toxic), so they
are used to give aromas to such things as candles and cleaning products. (See terpenes for
more information).
 Many pharmaceuticals have alkene functionality.
 Many other pharmaceuticals can be prepared from alkenes, via addition reactions such as
halogenation, hydration, and hydrohalogenation
• IUPAC Rules for Alkene Nomenclature
1) The ene suffix (ending) indicates an alkene or cycloalkene.
2) The longest chain chosen for the root name must include both carbon atoms of the
double bond.
3) The root chain must be numbered from the end nearest a double bond carbon atom.
If the double bond is in the center of the chain, the nearest substituent rule is used to
determine the end where numbering starts.
4) The smaller of the two numbers designating the carbon atoms of the double bond is
used as the double bond locator.
5) If more than one double bond is present the compound is named as a diene, triene or
equivalent prefix indicating the number of double bonds, and each double bond is
assigned a locator number.
6) Substituent groups containing double bonds are:
• - H2C=CH– Vinyl group
• - H2C=CH–CH2– Allyl group
 Lesson 2: Nomenclature of
Alkenes
Name
Rule 1: Molecular
Formula
Name
• Molecular
Formula Alkenes are named
using the same general
Ethene C2H4 Undecene C11H22 naming rules for
Propene C3H6 Dodecene C12H24 alkanes, except that the
Butene C4H8 Tridecene C13H26 suffix is now -ene.
Pentene C5H10 Tetradecene C14H28
Hexene C6H12 Pentadecene C15H30
Heptene C7H14 Hexadecene C16H32
Octane C8H16 Heptadecene C17H34
Nonene C9H18 Octadecene C18H36
Decene C10H20 Nonadecene C19H38
 Rule 2:
If the alkene contains only one double bond and that double bond is terminal,
then it is not necessary to place any number in front of the name. But if the
double bond is not terminal, they should be numbered in such a way as to give
the first of the two double-bonded carbons the lowest possible number and
should precede the "ene" suffix with a dash.

If the double bond is terminal If the double bond is not terminal

butane: correct: pent-2-ene
(CH3CH=CHCH2CH3CH3CH=CHCH2CH3)
C4H10 (CH3CH2CH2CH3CH3CH2CH2CH3)

butene: incorrect: pent-3-ene

(CH3CH2CH=CHCH3CH3CH2CH=CHCH3)
C4H8 (CH2=CHCH2CH3CH2=CHCH2CH3) *The second one is incorrect because flipping the formula horizontally
results in a lower number for the alkene.
Rule 3:
If there is more than one double bond in an alkene, all of the bonds should be
numbered in the name of the molecule - even terminal double bonds. The numbers
should go from lowest to highest, and be separated from one another by a comma.
The IUPAC numerical prefixes are used to indicate the number of double bonds.

octa-2,4-diene: CH3CH=CHCH=CHCH2CH2CH3CH3CH=CHCH=CHCH2CH2CH3
deca-1,5- diene: CH2=CHCH2CH2CH=CHCH2CH2CH2CH3CH2=CHCH2CH2CH=CHCH2CH2 CH2CH3
• Note that the numbering of "2-4" above yields a molecule with two
double bonds separated by just one single bond. Double bonds in such
a condition are called "conjugated", and they represent an enhanced
stability of conformation, so they are energetically favored as reactants
in many situations and combinations.
• Alkenes are molecules containing a C=C double bond. They are also referred
to olefins or unsaturated carbons sometimes because the C atoms in a C=C
double bond don’t have as many hydrogens bonded to them as an alkane does.
Contrast to this is the saturated which are alkene molecules with no double
bond

• Monounsaturated are molecules with one double bond.

• Polyunsaturated are molecules that have multiple double bonds

Let’s name more Alkenes!
• To name alkenes, we count the number of C atoms in the longest
unbranched chain, take the name of the corresponding alkane and change
–ane to -ene.

Thus…

Systematic: ethene propene butene

Common Name: ethylene propylene butylene
 What’s New
• Naming gets a little more complicated when we put double bonds in butene because
there's to places where we can put the double bond:
1. Between the first and second carbons
2. Between the second and third C atoms

• Possibilities of having a cis-trans isomers happens

when we put the double bond between the second and 1-butene
third C atoms.
• When we name molecules with double bond, we cis-2-butene trans-2-butene
should:
1. Pick out the longest chain with the double
bond (Any cis/trans isomers on 1-butene?)
2. Start numbering it from end closest to the
double bond.
 Let’s take a second example; drawing all the isomeric
pentenes:

cis-2-pentene
1-pentene

trans-2-pentene
If we move the C=C between the #3 and # 4 C you will see that in fact it is the same molecule
(flipped from left to right) as the 2-pentenes
 Naming Branched Alkenes

4,6-dimethyl-1-heptene
3-methyl-1-butene

• To name this molecule, we started from the right to

left to give the alkene the smallest value.
1-chloro-5-ethyl-2-flouro-6-methyl-1-octene

• In the above examples, giving the smallest

number to the C=C takes priority over giving a
small number to the methyl branch.
Lesson 3: Cycloalkenes
• Double bonds occur in rings • Some molecules think if one double
• Numbering starts from the double bond and bond is good, two double bonds are
goes around the ring to make C=C better. Indicate this by putting a
numbering 1 and 2 prefix directly in front of the -ene at
• If there are other groups on the ring, number the end of the name
around the ring in the direction that gives
smallest sum of numbers  Two double bonds = -diene
 Three double bonds = -triene
 Four double bonds =-tetraene
 Five double bonds = -pentaene
Cyclopentene 3 methyl cyclopentene 4-methylcyclohexene
 Six double bonds = -hexaene
 Example:

The shorthand notation for double

bonds is shown below:

is written
Draw the shorthand
notation and name the
molecules shown below:

Alternate double and single bonds are called

conjugated double bonds and are very common in
nature; they have distinctive chemical properties, often
absorb visible light, and as a result are often colored
compounds.
Group 1 members:

Zeane Veniz S. Santos Naomi Raine S. Rosario

Belldandy Zyle S. Villanueva Aerielle Gaea D. Oclay
Clarise T. Mamaril Chris Raewyn F. Cruz
Mark Jarcnel S. Bandong Charles Ernest C. Aguilar
Lyka Nicole F. Fernandez John Marcus M. Castro