Page|1

Republic of the Philippines

ISABELA STATE UNIVERSITY
Jones, Isabela

COLLEGE OF CRIMINAL JUSTICE EDUCATION

Second Semester, School Year 2021-2022

ORGANIC CHEMISTRY

I. TITLE OF THE MODULE

Chapter Three (3): ALKENE

II. INTRODUCTION

Two general types of hydrocarbons exist, saturated and unsaturated. Saturated

hydrocarbons, discussed in the previous chapter, include the alkanes and cycloalkanes. All
bonds in saturated hydrocarbons are single b-onds. Unsaturated hydrocarbons, the topic
of this chapter, contain one or more carbon–carbon multiple bonds. There are three classes
of unsaturated hydrocarbons: the alkenes, the alkynes, and the aromatic hydrocarbons, all
of which we will consider.

III. TABLE OF CONTENT

i. Unsaturated Hydrocarbons
ii. Characteristics if Alkenes and Cycloalkenes
iii. IUPAC Nomenclature for Alkenes and Cycloalkenes
iv. Alkenes as Substituents
v. Natural Occurring Alkenes
vi. Physical Properties of Alkenes and Cycloalkenes
vii. Chemical reaction of Alkenes

IV. LEARNING OUTCOME

At the end of this module, the students are expected to:

 Name and draw structures of alkenes
 Distinguish the difference of saturated and unsaturated hydrocarbons
 Distinguish reactions of alkenes and alkynes and their properties

V. LEARNING CONTENT

i. UNSATURATED HYDROCARBONS
An unsaturated hydrocarbon is a hydrocarbon in which one or more carbon–carbon
multiple bonds (double bonds, triple bonds, or both) are present. Unsaturated hydrocarbons
have physical properties similar to those of saturated hydrocarbons. However, their
chemical properties are much different. Unsaturated hydrocarbons are chemically more
reactive than their saturated counterparts. The increased reactivity of unsaturated
hydrocarbons is related to the presence of the carbon–carbon multiple bond(s) in such
compounds. These multiple bonds serve as locations where chemical reactions can occur.
Whenever a specific portion of a molecule governs its chemical properties, that portion
of the molecule is called a functional group. A functional group is the part of an organic
molecule where most of its chemical reactions occur. Carbon–carbon multiple bonds are
the functional group for an unsaturated hydrocarbon.
The study of various functional groups and their respective reactions provides the
organizational structure for organic chemistry. Each of the organic chemistry chapters The

General Chemistry (Organic Chemistry) - Crim AdGE

Isabela State University – Jones Campus
 Page|2

unsaturated hydrocarbon ethene is used to stimulate the ripening process in fruit that has
been picked while still green, such as bananas.
Unsaturated hydrocarbons are subdivided into three groups on the basis of the type of
multiple bond(s) present: (1) alkenes, which contain one or more carbon–carbon double
bonds, (2) alkynes, which contain one or more carbon–carbon triple bonds, and (3)
aromatic hydrocarbons, which exhibit a special type of “delocalized” bonding that involves
a six-membered carbon ring.
We begin our consideration of unsaturated hydrocarbons with a discussion of alkenes.
Information about alkynes and aromatic hydrocarbons then follows.

ii. CHARACTERISTICS IF ALKENES AND CYCLOALKENES

An alkene is an acyclic unsaturated hydrocarbon that contains one or more carbon–
carbon double bonds. The alkene functional group is, thus, a C—C group. Note the close
similarity between the family names alkene and alkane; they differ only in their endings:
-ene versus -ane. The -ene ending means a double bond is present.
The simplest type of alkene contains only one carbon–carbon double bond. Such
compounds have the general molecular formula CnH2n. Thus alkenes with one double
bond have two fewer hydrogen atoms than do alkanes (CnH2n-2).
The two simplest alkenes are ethene (C2H4) and propene (C3H6).
Comparing the geometrical shape of ethene with that of methane (the simplest alkane)
reveals a major difference. The arrangement of bonds about the carbon atom in methane is
tetrahedral, whereas the carbon atoms in ethene have a trigonal planar arrangement of
bonds; that is, they form a flat, triangle-shaped arrangement. The two carbon atoms
participating in a double bond and the four other atoms attached to these two carbon
atoms always lie in a plane with a trigonal planar arrangement of atoms about each
carbon atom of the double bond. Such an arrangement of atoms is consistent with the
principles of VSEPR theory.
A cycloalkene is a cyclic unsaturated hydrocarbon that contains one or more carbon–
carbon double bonds within the ring system. Cycloalkenes in which there is only one
double bond have the general molecular formula CnH2n-2. This general formula refl ects the
loss of four hydrogen atoms from that of an alkane (CnH2n-2). Note that two hydrogen
atoms are lost because of the double bond and two because of the ring structure.
The simplest cycloalkene is the compound cyclopropene (C3H4), a three-membered
carbon ring system containing one double bond.

Alkenes with more than one carbon–carbon double bond are relatively common.
When two double bonds are present, the compounds are often called dienes; for three
double bonds the designation trienes is used. Cycloalkenes that contain more than one
double bond are possible but are not common.

General Chemistry (Organic Chemistry) - Crim AdGE

Isabela State University – Jones Campus
 Page|3

iii. IUPAC NOMENCLATURE FOR ALKENES AND CYCLOALKENES

The IUPAC rules previously presented for naming alkanes and cycloalkanes can be
used, with some modification, to name alkenes and cycloalkenes.
Rule 1: The IUPAC rules previously presented for naming alkanes and
cycloalkanes can be used, with some modification, to name alkenes and
cycloalkenes.
Rule 2: Select as the parent carbon chain the longest continuous chain of carbon
atoms that contains both carbon atoms of the double bond.

Rule 3: Number the parent carbon chain beginning at the end nearest the double
bond.

Rule 4: Give the position of the double bond in the chain as a single number, which
is the lower-numbered carbon atom participating in the double bond.
This number is placed immediately before the name of the parent carbon
chain.

Rule 5: Use the suffixes -diene, -triene, -tetrene, and so on when more than one
double bond is present in the molecule. A separate number must be used
to locate each double bond.

Rule 6: Do not use a number to locate the double bond in unsubstituted cycloalkenes
with only one double bond because that bond is assumed to be between
carbons 1 and 2.
Rule 7: In substituted cycloalkenes with only one double bond, the double-bonded
carbon atoms are numbered 1 and 2 in the direction (clockwise or
counterclockwise) that gives the first-encountered substituent the lower
number. Again, no number is used in the name to locate the double
bond.

General Chemistry (Organic Chemistry) - Crim AdGE

Isabela State University – Jones Campus
 Page|4

Rule 8: In cycloalkenes with more than one double bond within the ring, assign one
double bond the numbers 1 and 2 and the other double bonds the lowest
numbers possible.

EXERCISE: IUPAC NAMES TO ALKENES AND CYCLOALKENES

iv. ALKENE AS SUBTITUENTS

Just as there are alkanes and alkyl groups, there are alkenes and alkenyl groups.
An alkenyl group is a noncyclic hydrocarbon substituent in which a carbon–carbon
double bond is present. The three most frequently encountered alkenyl groups are the
one-, two-, and three-carbon entities, which may be named using IUPAC
nomenclature (methylidene, ethenyl, and 2-propenyl) or with common names
(methylene, vinyl, and allyl).

The use of these alkenyl group names in actual compound nomenclature is

illustrated in the following examples.

v. NATURAL OCCURRING ALKENES

Alkenes are abundant in nature. Many important biological molecules are

characterized by the presence of carbon–carbon double bonds within their structure.
Two important types of naturally occurring substances to which alkenes contribute
are pheromones and terpenes.

PHEROMONES
A pheromone is a compound used by insects (and some animals) to transmit a
message to other members of the same species. Pheromones are often alkenes or alkene
derivatives. The biological activity of alkene-type pheromones is usually highly
dependent on whether the double bonds present are in a cis or a trans arrangement.
The sex attractant of the female silkworm is a 16-carbon alkene derivative
containing an —OH group. Two double bonds are present, trans at carbon 10 and cis
at carbon 12.

General Chemistry (Organic Chemistry) - Crim AdGE

Isabela State University – Jones Campus
 Page|5

This compound is 10 billion times more effective in eliciting a response from the
male silkworm than the 10-cis–12-trans isomer and 10 trillion times more effective
than the isomer wherein both bonds are in a trans configuration.
Insect sex pheromones are useful in insect control. A small amount of synthetically
produced sex pheromone is used to lure male insects of a single species into a trap. The
trapped males are either killed or sterilized. Releasing sterilized males has proved
effective in some situations. A sterile male can mate many times, preventing
fertilization in many females, who usually mate only once. Sex attractant pheromones
are now used to control the gypsy moth and the Mediterranean fruit fly.

TERPENES
A terpene is an organic compound whose carbon skeleton is composed of two or
more 5-carbon isoprene structural units. Isoprene (2-methyl-1,3-butadiene) is a five-
carbon diene.
Terpenes are formed by joining the tail of one isoprene structural unit to the head
of another unit.
In the human body, dietary beta-carotene (obtained by eating yellow-colored
vegetables) serves as a precursor for vitamin A; splitting of a beta-carotene molecule
produces two vitamin A molecules. An additional role of beta-carotene in the body,
independent of its vitamin A function, is that of antioxidant. An antioxidant is a
substance that helps protect cells from damage from reactive oxygen-derived species
called free radicals.

vi. PHYSICAL PROPERTIES OF ALKENES AND CYCLOALKENES

The general physical properties of alkenes and cycloalkenes include insolubility in
water, solubility in nonpolar solvents, and densities lower than that of water. Thus they
have physical properties similar to those of alkanes. The melting point of an alkene is
usually lower than that of the alkane with the same number of carbon atoms.
Alkenes with 2 to 4 carbon atoms are gases at room temperature. Unsubstituted
alkenes with 5 to 17 carbon atoms and one double bond are liquids, and those with still
more carbon atoms are solids.

vii. CHEMICAL REACTION OF ALKENES

Alkenes, like alkanes, are very flammable. The combustion products, as with any
hydrocarbon, are carbon dioxide and water.

Pure alkenes are, however, too expensive to be used as fuel. Aside from
combustion, nearly all other reactions of alkenes take place at the carbon–carbon
double bond(s). These reactions are called addition reactions because a substance is
added to the double bond. This behavior contrasts with that of alkanes, where the most
common reaction type, aside from combustion, is substitution.
An addition reaction is a reaction in which atoms or groups of atoms are added to
each carbon atom of a carbon–carbon multiple bond in a hydrocarbon or hydrocarbon
derivative. A general equation for an alkene addition reaction is

In this reaction, the A part of the reactant A—B becomes attached to one carbon
atom of the double bond, and the B part to the other carbon atom (see Figure 13.8). As
this occurs, the carbon–carbon double bond simultaneously becomes a carbon–carbon
single bond.

General Chemistry (Organic Chemistry) - Crim AdGE

Isabela State University – Jones Campus
 Page|6

Addition reactions can be classified as symmetrical or unsymmetrical. A

symmetrical addition reaction is an addition reaction in which identical atoms (or
groups of atoms) are added to each carbon of a carbon–carbon multiple bond. An
unsymmetrical addition reaction is an addition reaction in which different atoms (or
groups of atoms) are added to the carbon atoms of a carbon–carbon multiple bond.

SYMMETRICAL ADDITION REACTIONS

The two most common examples of symmetrical addition reactions are
hydrogenation and halogenation.
A hydrogenation reaction is an addition reaction in which H2 is incorporated into
molecules of an organic compound. In alkene hydrogenation a hydrogen atom is added
to each carbon atom of a double bond. It is accomplished by heating the alkene and H2
in the presence of a catalyst (usually Ni or Pt).

The identity of the catalyst used in hydrogenation is specified by writing it above

the arrow in the chemical equation for the hydrogenation. In general terms,
hydrogenation of an alkene can be written as

The hydrogenation of vegetable oils is a very important commercial process today.

Vegetable oils from sources such as soybeans and cottonseeds are composed of long-
chain organic molecules that contain several double bonds. When these oils are
hydrogenated, they are converted to low-melting solids that are used in margarines and
shortenings.
A halogenation reaction is an addition reaction in which a halogen is incorporated
into molecules of an organic compound. In alkene halogenation a halogen atom is
added to each carbon atom of a double bond. Chlorination (Cl2) and bromination (Br2)
are the two halogenation processes most commonly encountered. No catalyst is needed.

In general terms, halogenation of an alkene can be written as

Bromination is often used to test for the presence of carbon–carbon double bonds
in organic substances. Bromine in water or carbon tetrachloride is reddish brown. The

General Chemistry (Organic Chemistry) - Crim AdGE

Isabela State University – Jones Campus
 Page|7

dibromo compound(s) formed from the symmetrical addition of bromine to an organic

compound is(are) colorless. Thus the decolorization of a Br2 solution indicates the
presence of carbon–carbon double bond.

UNSYMMETRICAL ADDITION REACTIONS

Two important types of unsymmetrical addition reactions are hydrohalogenation
and hydration.
A hydrohalogenation reaction is an addition reaction in which a hydrogen halide
(HCl, HBr, or HI) is incorporated into molecules of an organic compound. In alkene
hydrohalogenation one carbon atom of a double bond receives a halogen atom and the
other carbon atom receives a hydrogen atom. Hydrohalogenation reactions require no
catalyst. For symmetrical alkenes, such as ethene, only one product results from

hydrohalogenation.
A hydration reaction is an addition reaction in which H2O is incorporated into
molecules of an organic compound. In alkene hydration one carbon atom of a double
bond receives a hydrogen atom and the other carbon atom receives an —OH group.

Alkene hydration requires a small amount of H2SO4 (sulfuric acid) as a catalyst. For
symmetrical alkenes, only one product results from hydration.
In this equation, the water (H2O) is written as H—OH to emphasize how this
molecule adds to the double bond. Note also that the product of this hydration reaction
contains an —OH group. Hydrocarbon derivatives of this type are called alcohols.
When the alkene involved in a hydrohalogenation or hydration reaction is itself
unsymmetrical, more than one product is possible. (An unsymmetrical alkene is one in
which the two carbon atoms of the double bond are not equivalently substituted.) For
example, the addition of HCl to propene (an unsymmetrical alkene) could produce
either 1-chloropropane or 2-chloropropane, depending on whether the H from the HCl

attaches itself to carbon 2 or carbon 1.

When two isomeric products are possible, one product usually predominates. The
dominant product can be predicted by using Markovnikov’s rule, named after the
Russian chemist Vladimir V. Markovnikov. Markovnikov’s rule states that when an
unsymmetrical molecule of the form HQ adds to an unsymmetrical alkene, the hydrogen
atom from the HQ becomes attached to the unsaturated carbon atom that already has
the most hydrogen atoms. Thus the major product in our example involving propene is
2-chloropropane.

POLYMERIZATION OF ALKENES: ADDITION ALKENES

A polymer is a large molecule formed by the repetitive bonding together of many

smaller molecules. The smaller repeating units of a polymer are called monomers. A

General Chemistry (Organic Chemistry) - Crim AdGE

Isabela State University – Jones Campus
 Page|8

monomer is the small molecule that is the structural repeating unit in a polymer. The
process by which a polymer is made is called polymerization. A polymerization
reaction is a chemical reaction in which the repetitious combining of many small
molecules (monomers) produces a very large molecule (the polymer). With appropriate
catalysts, simple alkenes and simple substituted alkenes readily undergo
polymerization.
The type of polymer that alkenes and substituted alkenes form is an addition
polymer. An addition polymer is a polymer in which the monomers simply “add
together” with no other products formed besides the polymer.
The simplest alkene addition polymer has ethylene (ethene) as the monomer. With
appropriate catalysts, ethylene readily adds to itself to produce polyethylene.

An exact formula for a polymer such as polyethylene cannot be written because the
length of the carbon chain varies from polymer molecule to polymer molecule. In
recognition of this “inexactness” of formula, the notation used for denoting polymer
formulas is independent of carbon chain length. We write the formula of the simplest
repeating unit (the monomer with the double bond changed to a single bond) in
parentheses and then add the subscript n after the parentheses, with n being understood
to represent a very large number. Using this notation, we have, for the formula of
polyethylene,

This notation clearly identifies the basic repeating unit found in the polymer.

POLYMERIZATION OF ALKENES: ADDITION ALKENES

Many substituted alkenes undergo polymerization similar to that of ethene when

they are treated with the proper catalyst. For a monosubstituted-ethene monomer, the
general polymerization equation is
Variation in the substituent group Z can change polymer properties dramatically,
as is shown by the entries in Table 13.1, a listing of monomers for the fi ve ethene-
based polymers polyethylene, polypropylene, poly(vinyl chloride) (PVC), Teflon, and
polystyrene, along with several uses of each.
The properties of an ethene-based polymer depend not only on monomer identity
but also on the average size (length) of polymer molecules and on the extent of polymer
branching. For example, there are three major types of polyethylene: high-density
polyethylene (HDPE), low-density polyethylene (LDPE), and linear low-density
polyethylene (LLDPE). The major difference among these three materials is the degree
of branching of the polymer chain. HDPE and LLDPE are composed of linear,
unbranched carbon chains, while LDPE chains are branched. The strong and thick
plastic bags from a shopping mall are LLDPE, the thin and flimsy grocery store plastic
bags are HDPE, and the very wispy garment bags dry cleaners use are LDPE.
In general, HDPE materials are rigid or semi-rigid with uses such as threaded bottle
caps, toys, bottles, and milk jugs whereas LDPE materials are more flexible with uses
such as plastic film and squeeze bottles. Objects made of HDPE hold their shape in
boiling water, whereas objects made of LDPE become severely deformed at this
temperature. With their alkane-like structures, ethene-based addition polymers are very

General Chemistry (Organic Chemistry) - Crim AdGE

Isabela State University – Jones Campus
 Page|9

unreactive, as are alkanes. This unreactivity means that these polymers do not readily
decompose when they are deposited into landfill sites.
Decreasing availability of space at landfills has led to an increasingly important
plastics recycling industry. Because of the wide diversity of addition polymers in
consumer products, recycling requires sorting the polymers into various subtypes,
which are then recycled separately.
To standardize the recycling process manufacturers now place recycling symbols
on their products, identifying the type of addition polymer present.

BUTADIENE-BASED ADDITIONAL POLYMERS

When dienes such as 1,3-butadiene are used as the monomers in addition

polymerization reactions, the resulting polymers contain double bonds and are thus still
unsaturated.

In general, unsaturated polymers are much more flexible than the ethene-based
saturated polymers listed in Table 13.1. Natural rubber is a flexible addition polymer
whose repeating unit is isoprene (Section 13.7)—that is, 2-methyl-1,3-butadiene.

ADDITIONAL COPOLYMERS
Saran Wrap is a polymer in which two different monomers are present:
chloroethene (vinyl chloride) and 1,1-dichloroethene. Such a polymer is an example of
a copolymer. A copolymer is a polymer in which two different monomers are present.
Another important copolymer is styrene–butadiene rubber, the leading synthetic rubber
in use today. It contains the monomers 1,3-butadiene and styrene in a 3:1 ratio. It is a
major ingredient in automobile tire.

General Chemistry (Organic Chemistry) - Crim AdGE

Isabela State University – Jones Campus
 P a g e | 10

VI. ASSESSMENT

1. How does an unsaturated hydrocarbon differ structurally from a saturated hydrocarbon?

2. What is the functional group present in an alkene?
3. In general terms, compare the physical properties of unsaturated and saturated
hydrocarbons.
4. In general terms, compare the chemical properties of unsaturated and saturated
hydrocarbon.
5. Classify each of the following hydrocarbons as saturated or unsaturated.

6. Write the molecular formula for hydrocarbons with each of the following structural
features.
a. Acyclic, four carbon atoms, no multiple bonds
b. Acyclic, five carbon atoms, one double bond
c. Cyclic, five carbon atoms, one double bond
d. Cyclic, seven carbon atoms, two double bonds
7. Assign an IUPAC name to each of the following unsaturated hydrocarbons

8. Draw a condensed structural formula for each of the following unsaturated hydrocarbons.
a. 3-Methyl-1-pentene
b. 3-Methylcyclopentene
c. 1,3-Butadiene
d. 3-Ethyl-1,4-pentadiene
General Chemistry (Organic Chemistry) - Crim AdGE
Isabela State University – Jones Campus
 P a g e | 11

9. The following names are incorrect by IUPAC rules. Determine the correct IUPAC name
for each compound.
a. 2-Methyl-4-pentene
b. 3-Methyl-2,4-pentadiene
c. 3-Methyl-3-cyclopentene
d. 1,2-Dimethyl-3-cyclohexene
10. Draw a line-angle structural formula for each of the following unsaturated hydrocarbons.
a. 1-Pentene
b. 2-Pentene
c. 1,4-Pentadiene
d. 4-Methyl-2-pentene
11. Name, using IUPAC rules, each of the following unsaturated hydrocarbons.

VII. RESOURCES
 Sachkheim, George I. and Lehman Denis D. Chemistry for the Health Sciences. 8th
Edition. Prentice-Hall, Inc.
 Stoker, Stephen H. General, Organic, and Biological Chemistry. 5th Edition.
Brooks//Cole, Cenage Learning. 2010
 Holm, Johanna Forgotten Chemistry. Barron’s Educational Series, Inc. 2006

General Chemistry (Organic Chemistry) - Crim AdGE

Isabela State University – Jones Campus