Chapter 7 Alkenes
7.1 Alkenes
Alkenes are hydrocarbons molecules with carbon-carbon double bond
(-C=C-) structure.
Also known as unsaturated compounds or olefins
General formula for alkenes and cycloalkenes are:
~ Alkenes : CₙH₂ₙ ; n ≥ 2
~ Cycloalkenes : CₙH₂ₙ₋₂ ; n≥3
7.2 Nomenclature
7.2.1 Nomenclature of Straight-chain Alkenes
Naming organic compound follows IUPAC rules.
IUPAC name for an unbranched chain of an alkene consist 2 part:
~ Prefix : Indicates the number of carbon atoms in the chain
~ Suffix : -ene to show that the compound is an alkane
Table below shows the first 7 alkanes:
Naming a branched-chain alkanes consist 2 parts which are parent
name and substituent names.
Steps of naming alkanes with branched-chain shown below:
Step 1 : Identify the parent chain by finding the longest continuous chain
of carbon atoms in the molecule. In this case, the parent chain consists of
seven carbon atoms, so it is a heptane chain.
Step 2 : Identify the substituents and number the carbon atoms in the
parent chain starting from one end to the other, giving the substituents
the lowest possible numbers. In this molecule, we have an alkyl group
(methyl, CH₃) and 2 double bond.
Step 3 : Since we have a methyl group attached to the third carbon atom,
we name it as "3-methyl".For the double bond, we indicate its presence by
using the prefix "diene" and specify the locations of the double bonds as
"-2,5-" since it starts from the second carbon atom and extends to the
fifth carbon atom.
Step 4 : Put all the pieces together to get the final name: "3-methylhept-
2,5-diene".
7.2.2 Nomenclatures of cycloalkenes
IUPAC name for cycloalkenes is obtained by adding the prefix cyclo- to
the name of alkene.
Figure below shows example of cycloalkenes:
Steps of naming alkanes with branched-chain shown below
Step 1 :Identify the longest carbon chain that contains double bond as a
parent chain. The parent chain in this molecule is cyclohexene, as it forms
a ring structure and contains the most carbon atoms.
Step 2 : identify the substituents and number the carbon atoms in the
parent chain starting from one end to the other, giving the substituents
the lowest possible numbers. In this molecule, we have an alkyl group
(ethyl, CH₃CH₂), and 2 halogen group (bromo and chloro).
Step 3 : Since there is one ethyl attached to carbon 1 (making it "1-ethyl"),
a bromine atom (Br) attached to carbon 3 (making it "3-bromo"), and a
chlorine atom (Cl) attached to carbon 5 (making it "5-chloro").
Step 4 : Put all the pieces together to get the final name: "3-bromo-5-
chloro-1-ethylcyclohexene"
7.3 Boiling point of alkenes and Cycloalkenes
Most alkenes exhibit only weak van der Waals interactions.
As the size of alkene molecules increases, the strength of these
interactions also increases, leading to higher boiling points.
Alkenes with four or more carbon atoms can have cis-trans
isomerism.
But-2-ene has two isomers: cis-but-2-ene and trans-but-2-ene.
The boiling points of these isomers are 4°C and 1°C, respectively.
In cis-but-2-ene, the two methyl (CH₃) groups are on the same side,
making the molecule more polar.
This higher polarity results in a higher boiling point for cis-but-2-ene.
In trans-but-2-ene, the two methyl groups are on opposite sides,
canceling out each other's polarity.
As a result, trans-but-2-ene has a lower boiling point compared to cis-
but-2-ene.
7.4 Preparation of Alkene
7.4.1 Dehydration of Alcohols
This reaction involves elimination of water from alcohols to form an
alkene.
7.4.2 Dehydrohalogenation of Alkyl Halides
This reaction requires elimination of hydrogen and a halogen from
alkyl halide to form an alkene.
7.5 Reaction of Alkenes( Addition reaction)
7.5.1 Addition of hydrogen to an alkene
Addition of hydrogen (H₂) to an alkene to produce an alkane in the
presence of nickel (Ni), palladium (Pd) or platinum (Pt) catalyst
7.5.2 Addition of halogen to an alkene
Addition of halogen (Cl₂ or Br₂) to an alkene to produce an alkane in
the presence of inert solvent(CH₂Cl₂).
7.5.3 Addition of halogen in water to an alkene
Addition of halogen in water to an alkene that occur spontaneously at
room temperature to produced haloalcohol.
7.5.4 Addition of hydrogen halide to an alkene
Addition of hydrogen halide (HCl or HBr) to an alkene to produced a
haloalkane
Markonikov’s rule is a rule where the hydrogen atom added to carbon
that have higher number of hydrogen atom.
Example of Markonikov’s rule shown below:
The mechanism of electrophile addition for hydrogen halides that
follows Markonikov’s rule are presented below:
The reaction between alkene and hydrogen bromide, HBr in the
presence of hydrogen peroxide (H₂O₂ )/acid peroxide is known as Anti-
Markonikov’s(A.M.) rule.
Figure below shows the example of chemical equation for (A.M.)
7.5.5 Addition of acidified water to an alkene
Addition of water (H₂O) to an alkene to produced alcohol in the
presence of acid as catalyst.
The mechanism of electrophile addition for alkenes in acidified water
that follows Markonikov’s rule are presented below:
Step 1 :
Step 2:
7.6 Oxidation reaction
7.6.1 Oxidation of alkenes with cold,dilute alkaline potassium
permanganate (VII),KMnO₄ solution.
Alkenes react with cold, diluted KMnO₄ solution conditions produce
glycols.
Example is shown below:
7.6.2 Oxidation of alkenes with hot, concentrated acidified potassium
permanganate (VII),KMnO₄ solution.
Alkenes react with hot, concentrated KMnO₄ conditions produce
carbonyl compounds (ketones or carboxylic acid).
General examples are shown below:
7.6.3 Oxidation of alkenes with Ozone
The reaction of an alkene with ozone, O₃ (ozonolysis) to yield both
ketone and aldehyde in the present of O₃ followed by Zn and H₂O, or
O₃ followed by (CH₃)₂S
General examples are shown below:
7.7 Identification test for alkenes
Identification test is done to differentiate between alkenes
(unsaturated compound) and alkanes (saturated compound)
There are mainly 3 test that can be done which are :
~ Baeyer’s test using Cold, Dilute Alkaline KMnO₄ solution
~ Bromine in Methylene Chloride
~ Bromine water
The reaction is shown below: