ALKENES AND
CYCLOALKENES
Alkenes
• Also called olefins
• Family of Hydrocarbons
• Unsaturated hydrocarbons containing at least
one C-C double bond
• General Formula: C nH 2n
• Functional group; Carbon-Carbon double bond
Why there is no alkene formed with only one carbon atom?
Alkene Synthesis via β elimination reactions
Two atoms on adjacent carbon atoms are removed, resulting in the formation of a
double bond.
• Dehydration of Alchohol -a molecule of water is eliminated from an alcohol molecule by heating
the alcohol in the presence of a strong mineral acid. A double bond forms between the adjacent
carbon atoms that lost the hydrogen ion and hydroxide group.
• Dehydrohalogenation of alkyl halides. -another β elimination reaction,
involves the loss of a hydrogen and a halide from an alkyl halide (RX).
Dehydrohalogenation is normally accomplished by reacting the alkyl
halide with a strong base, such as sodium ethoxide.
• Dehalogenation -Vicinal dihalides, which are alkane molecules that
contain two halogen atoms on adjacent carbon atoms, can form
alkenes upon reaction with zinc.
Physical Properties of
Alkenes
1. Physical State – gases, liquids and solids at room temperature.
2. Density – less dense in water
3. Solubility - dissolve in organic solvents
- insoluble in water
4. Boiling/Melting Points - low
5. Polarity – Non polar
Note: Intermolecular forces of alkenes gets stronger with increase in the
size of the molecules.
Chemical Properties of
Alkene
1. Combustion Reaction - substance reacts with oxygen from the air and transfers
energy to the surroundings as light and heat.
Ex: Burning coal, methane gas, and sparklers
*Complete Combustion – produced CO2 + H2O
- flame is mostly heat and a little light
C2H4 + O2 → CO2 + 2H2O
*Incomplete Combustion- insufficient oxygen is available
- produced CO/C gas + H2O
-more light is produced rather than heat
C2H4 + 2O2 → 2CO + 2H2O
C H + O → 2C + 2H O
2. Addition Reaction - occurs when two or more reactants combine to
form a single product. This product will contain all the atoms that were
present in the reactants.
• With hydrogen
• With water
• With halogens
3. Polymerization Reaction - any process in which relatively small
molecules, called monomers, combine chemically to produce a very
large chainlike or network molecule, called a polymer.
Bonding in Alkenes
C=C bonds consist of a sigma bond and a pi bond.
• Sigma bond – results from end-to-end overlap of S orbitals between the bonding atoms
- strongest type of covalent bond
• Pi bond - sideways overlap of adjacent P orbitals above and below the carbon atoms
- more easily broken
Cycloalkene
• sometimes called a cycloolefin
• type of alkene hydrocarbon which contains a closed ring of
carbon atoms.
• prefix cyclo- comes from ancient Greek means round.
• General Formula: CnH2(n-m)
Synthesis of Cycloalkene
Cycloalkenes and cycloalkynes are normally prepared
from cycloalkanes by ordinary alkene‐forming
reactions, such as dehydration, dehalogenation, and
dehydrohalogenation.
Physical properties
• Cycloalkenes are unsaturated and therefore have fewer hydrogen atoms and
fewer bonds, as opposed to open-chain alkenes, which means that there is
less internal energy within the molecule.
• Most cycloalkenes are liquid at room temperature, though have very low
solubility in water. Only the first few cycloalkenes are gases. Cycloalkenes are
rarely solid at room temperature.
• Essentially, cycloalkenes have similar physical properties to alkenes and
cycloalkanes aside from the fact that cycloalkenes have at least one double
bond.
Chemical Properties
Cycloalkenes share similar chemical properties to cycloalkanes such as:
- The smaller the ring, the more likely it is to undergo reactions due to the
carbon-carbon bond angle. For example, the smallest cycloalkene-
Cyclopropene is very reactive and has a extremely high strain. Larger
compounds show very little ring strain and are less reactive.
-Undergo combustion and Halogenation reactions
However there are also some differences. Cycloalkenes generally are more
reactive than Cycloalkanes due to their double carbon-carbon bond.
Cycloalkenes also undergo addition reactions, which occurs when the pi bond is
broken and two new sigma bonds are formed
Naming Alkenes
Suffix: -ene
1. Name the parent hydrocarbon by locating the longest carbon chain that
contain the double bond and name it according to the number of carbons
with the suffix –ene.
2. (a.) Number the carbons of the parent chain so the double bond
carbons have the lowest possible numbers.
(b.) If the double bond is equidistant from each end, number so the first
substituent has the lowest number.
3. Write out the full name, numbering the substituents according to their
position in the chain and list them in alphabetical order.
4. Indicate the double bond by the number of the first alkene carbon.
5. If more than one double bond is present, indicate their position by
using the number of the first carbon of each double bond and use the
suffix –diene (2 double bonds), -triene ( 3 double bonds), -tetraene ( 4
double bonds), etc.
Naming Cycloalkene
a. Cycloalkenes are named in a similar way. Number the cycloalkane so
the double bond carbons get numbers 1 and 2, and the first substituent
is the lowest possible number.
b. If there is a substituent on one of the double bond carbons, it
gets number 1.
Practice.
1-hexene
Line-bond structure Condensed Structure Skeletal Structure
2,3,4-trimethyl-1-hexene Cyclohexene
2,3-dimethyl-2-butene
1-Methylcyclopentene
3,5-dimethylcyclohexene
4-isopropyl-2-methyl-1-nonene
Line-bond structure Condensed Structure Skeletal Structure
2,3-dimethyl-1-cyclobutene 3-methylcyclobutene 4-ethyl-3-methyl-3-hexene
Where do Alkenes come from?
• produced by thermal cracking
• The small quantities of ethane, propane, and butane found in natural
gas are converted into ethene. It can be produced by thermal cracking
of ethane to produce ethene and a hydrogen molecule.
What are the uses of Alkenes?
• Ethylene and propylene are the largest-volume industrial organic
chemicals.
• Alkenes are the raw materials for a number of plastics such as
polyethylene, PVC, polypropylene, and polystyrene.
Polythene is most popular plastic.
POLYVINYL CHLORIDE (PVC)
-synthetic resin made frim polymerization of vinyl chloride
Production of Ethanol
hydration of ethene
Source and Application of Cycloalkene
Alkyl-substituted cycloalkenes are frequently found in nature including two important
classes of natural products, terpenes and steroids. Both share similar biosyntheses and in
most cases cyclic structures.
Steroids are widespread in the animal and plant kingdom. Most of the steroids possess a
basic structure consisting of four rings and 21-30 carbon atoms. This class includes the
important groups of sex hormones, adrenocortical hormones, bile acids, and toad
venoms.
Terpenes are natural products which are constructed from isoprene (isoprene=2-methyl-
1,3-butadiene) units leading to mostly cyclic or even polycyclic structures
-represent the primary constituents of the essential oils of plants from which they can be
generated by steam distillation. They are used widely as fragrancies in perfumery and as
spices. Additionally, they are employed as starting materials in the syntheses of vitamins.
End.
