Selected Topic in Organic Chemistry

I. Objectives
 Describe alkenes.
 Name some alkenes using IUPAc System of Nomenclature.
 Draw structure of alkenes based on the given IUPAC names.
 Give some uses of alkenes.

II. a. Topic Alkenes: Structure and Reactivity

1. Naming and Uses of Alkenes

b. References
McMurry, John, Fundamentals of Organic Chemistry, 5th edition. Pp. 74-77.
https://www.slideshare.net/zentaquqen/chapter-3-alkenes
https://www.americanchemistry.com./ProductsTechnology/Olefins
https://www.Chem.libretexts.org/Bookshelves/Organic_Chemistry)/Alkenes/Naming_the
_Alkenes.

III. Discussion

Alkenes are also called olefins, From the Greek word olefiant meaning oil forming.
Alkene has a general formula of CnH2n. These are hydrocarbons that contain carbon-carbon
double bond (C=C). Because of their double bond, alkenes have fewer hydrogens per carbon
than related alkanes and are therefore referred to as unsaturated. Ethylene (Ethene), for
example, has formula C2H4, whereas ethane has the formula C2H6.

Naming of Alkenes
Alkenes are named according to a series of rules of International Union of Pure and
Applied Chemistry (IUPAC) similar to those for alkanes, with the suffix –ene used in place of –
ane to identify the family.
A chemical name has 3 parts in the IUPAC system of nomenclature:

The parent name selects a main part of the molecule and tells how many carbon atoms
are in that part, the suffix identifies the functional group family that the molecule belongs to,
and the prefix specifies the location (s) of various substituents on the main part.

The following are the steps in naming alkenes:

1. Name the parent hydrocarbon.
Find the longest carbon chain that contains the double bond, and name the compound
using the suffix –ene.

2. Number the carbon atoms in the chain.

Begin numbering at the end nearer the double bond. If the double bond is equidistant
from the two ends, begin numbering at the end nearer the first branch point. This rule
ensures that the double bond carbons receive the lowest possible numbers.

3. Write the full name.

Number the substituents according to their position in the chain and list them
alphabetically. Indicate the position of the double bond by giving the number of the first
alkene carbon. If more than one double bond is present, give the position of each and
use one of the suffixes –diene for 2 double bonds, -triene for 3 double bonds, tetraene
for 4 double bonds and so on. Use commas to separate numbers and hyphens to
separate words from numbers.
 Cycloalkenes (contains C=C in the ring) are named in a similar way, but because there
is no chain end to begin from, we 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. Note that it’s not
necessary to specify the position of the double bond in the name because it’s always between
C1 and C2.

For historical reason reasons, there are few alkenes whose names don’t conform to the
rules. For example, the alkene corresponding to ethane should be called ethene, but the name
ethylene has been used for so long that it is accepted by IUPAC.

Many Alkenes are Known by Common Names

Uses of Alkenes

Alkenes occur abundantly in nature, and many have important uses.

 Ethylene also called ethene is the basic building block for the chemistry industry and
is the largest volume organic chemical produced in the U.S. and globally. It is used as feedstock
in the production of polyethylene and other polymers and production of other industrial
chemicals such as ethylene oxide, ethylene glycol, and ethylene dichloride. Polymers of ethylene
are used to manufacture fibers, bins, pails, crates, bottles, piping, food packing films, trash
lines, bags, wire and cable sheating, insulation, surface coating for paper and cardboard, and
wide variety of other products including tile, and flooring for building and construction. Ethylene
is also used to manufacture other chemiclas that are used as antifreeze, solvents, surfactants,
detergents, polyglycols, and ethanolamine. Minor uses of ethylene are: as gas fuels in welding
and cutting operations, in petrochemical industries as a refrigerant, and in commercial
greenhouses as ripening agent for fruits and vegetables.

Propylene exist naturally in the environment, where it is produced by vegetation and

emitted from certain tree species. Propylene is also a combustion product from motor vehicle
exhaust, aircraft exhaust and cigarette smoke. Essentially, all the propylene produced
commercially is use ac chemical intermediate in other chemical manufacturing process. Major
uses are the production of polypropylene, propylene oxide, and other industrial chemicals such
as acrylonitrite, oxo chemicals, and acrylic acid.

Butadiene is primarily used as monomer in the production of polymers such as

synthetic rubbers or elastomers. Polymers made from butadiene are used in making tires,
carpet backing, plastic gloves, wetsuits, rubber hoses, and gaskets.

Alkenes are very Important in the manufacture of plastics. All plastics in some way are
related to alkenes. The name of some plastics (Polythene or polyethene, Polypropene), relate to
their alkene names.
Polyethene is the most popular plastic. It is used as grocery bags, shampoo bottles,
children's toy, bullet proof vests, film wrapping and kitchenware.

Polyvinyl Chloride (PVC) is used for clothing. PVC fabric has a sheen to it and is
waterproof. It is also used as coats, shoes, jackets, aprons and bags and as the insulation on
electric wires. PVC is used in producing pipes for various municipal and industrial applications.
For examples, for drinking water distribution and wastewater mains. PVC is also used ceiling
tiles, and as a composite for the production of accessories or housings for portable electronics.
uPVC or Rigid PVC is used in the building industry as a low-maintenance material.

IV. Evaluation

Give the IUPAC name of the following alkenes.

 a.

b.

c.

d.

e.

2. Draw the structure for each compound.

a. 2-ethyl-1-hexene
b. Cyclopentene`

3. Give three (3) uses of alkenes.