Chapter 3

Alkenes
Alkenes
• Unsaturated
– contain carbon-carbon double and triple bond to which
more hydrogen atoms can be added.
• Alkenes: carbon-carbon double bonds
• Alkynes: carbon-carbon triple bonds.
Alkenes
Saturated compounds (alkanes):

Have the maximum number of hydrogen
atoms attached to each carbon atom.
Unsaturated compounds:
Have fewer hydrogen atoms attached to
the carbon chain than alkanes.
• Containing double bond are alkenes.

CnH2n
• Containing triple bonds are alkynes.
CnH2n-2
Alkenes CnH2n “unsaturated” hydrocarbons
H H
C2H4 ethylene C C
H H
Functional group = carbon-carbon double bond
sp2 hybridization => flat, 120o bond angles
σ bond & π bond => H2C=CH2
No rotation about double bond!

Naming Alkenes and Alkynes
(Unsaturated Compounds)
Alkanes contain single bonds only -ANE ending

CnH2n+2 (saturated)
Alkenes contain a double bond -ENE ending

CnH2n (unsaturated)
Alkynes contain a triple bond between -YNE ending

CnH2n-2 (unsaturated)
Naming Alkenes & Alkynes
Name & position Change the
of branching Indicate where
+ double or triple + ending of the
groups parent name to
bond is located
(if any) - ene or -yne
Parent Name = longest continuous chain of carbon atoms
Use Greek prefixes to indicate the presence of multiple

identical branching groups.
Naming Alkenes and Alkynes
• IUPAC nomenclature rules for alkenes and alkynes are similar to

alkanes.
• Step 1. Name the parent compound. Find the longest chain

containing the double or triple bond, and name the parent compound by
adding the suffix –ene or –yne to the name of the main chain.
• Step 2: Number the carbon atoms in the parent chain, beginning at
the end nearest to the double or triple bond. If the multiple bond is an
equal distance from both ends, begin numbering at the end nearer the
first branch point. The number indicates which carbon the multiple
bond is AFTER. (i.e. between 2 and 3 is 2-)
• Step 3: Assign numbers and names to the branching substituents,

and list the substituents alphabetically. Use commas to separate
numbers, and hyphens to separate words from numbers.
• Step 4. Indicate the position of the multiple-bond carbon.
If more than one multiple bond is present, identify the
position of each multiple bond and use the appropriate
ending diene, triene, tetraene, and so forth.
• Step 5. Assemble the name

IUPAC Names of First Four Linear Alkenes
Cl
H3C C CH2
H H3C C C CH3
H
Prop-1-ene/1-propene 2-chlorobut-2-ene/2-chloro-2-
butene
Br
H2C C C C C CH3
H H H H
Br 5-bromohexa-1,3-diene
Cl
5-bromo-2-ethylcyclopenta-1,3- 5-chloro-4-
diene methylcyclohept-1-ene
C2H5
Multiple Double/Triple Bonds
Physical Properties
• Similar to alkane
• relatively low mp/bp, increases as no of C increase
• Branched alkene has lower bp
• Insoluble in water
• Non-polar or weakly polar
• No hydrogen bonding
Importance:
common group in biological molecules
starting material for synthesis of many plastics
Synthesis of alkene
(a) Dehydration of alcohols
The -OH group
Alcohols (R-OH) & aare
H atom from the(loss
dehydrated nextofcarbon atom in the when
water molecules) chain
will be removed.
heated with concentrated sulphuric acid (H2SO4) or concentrated
Reagent
phosphoric: conacid
. H2SO / con.
(H34PO 4). H3PO4 (catalyst)
Condition : ∆ at 170 oC
examples:
Zaitsev rule / Saytzeff rule
 Zaitsev rule may be used to predict the major and minor
products of elimination reactions.
 The rule states that the major product is the alkene with a
greater number of alkyl groups bonded to the carbon atom with
the double bond.
alkenes which contain more alkyl groups will be the major product.
 For example, in the dehydration of 2-butanol, 2-butene (the

major product) has two methyl groups bonded to the carbon
atom with the double bond, while 1-butene (the minor product)
has only one ethyl group.
(b) Dehydrohalogenation of haloalkanes
Haloalkanes (RX) react with NaOH or KOH in ethanol (as solvent) to
form alkenes.
examples:
1-bromo-1-methylcyclopentane
Example
Write a chemical equation for the reaction of (CH3)2CH-CBr(CH3)2 with hot
ethanolic KOH solution, and name the major product of the reaction.
Chemical Properties
(a) Hydrogenation
Alkenes react with hydrogen gas at room temperature in the
presence of Pt, Pd or Ni to give alkanes.
R R
R R Pt / Pd / Ni
C C + H2 R C C R
R R
H H
(b) Addition of hydrogen halides
Alkenes react with hydrogen halides (HCl, HBr, or HI) at
room temperature to form haloalkanes.
example:
Note: H+ ion adds to C-1 (with two H atoms), and not C-2 (with
only one H atom). This is in accordance to Markovnikov’s
rule, which states:
WHEN A HYDROGEN HALIDE ADDS TO AN ASYMMETRIC
ALKENE, THE ADDITION OCCURS SUCH THAT THE
HALOGEN ATTACHES ITSELF TO THE CARBON OF ALKENE
BEARING THE LOWEST NO. OF HYDROGEN ATOMS.
The reaction between 3-methyl-1-butene with HCl to give 2-
chloro-3-methylbutane (major product) and 1-chloro-3-
methylbutane (minor product) is:
HCl +
In the presence of hydrogen / organic peroxides (RO-OR), alkenes

react with HCl to give haloalkanes that do not follow
Markovnikov’s rule (anti-Markovnikov). For example:
+ HCl
(c) Halogenation
Halogens (Cl2 or Br2) adds to the C=C of alkenes & cycloalkenes at
room temp., in the dark, and using inert solvents, such as
dichloromethane (CH2Cl2) or tetrachloromethane (CCl4), to give
haloalkanes.
This is an example of an electrophilic addition reaction.
example:
(d) Hydration
Alkenes react with water (H2O) to give alcohols. The
reaction is catalysed by dilute acid.
It involves the addition of H and OH to the –C=C- according to
Markovnikov’s rule.
The electrophile is H3O+. For example:
H2SO4
+ H2O
(e) Oxidation
i) The reaction is alkenes with basic dilute, cold potassium
permanganate
(KMnO4). It involves addition of two -OH groups to each carbon atom with
the double bond.
For example:
This reaction, known as Baeyer test, may be used to distinguish

unsaturated hydrocarbons from saturated hydrocarbons.
ethene (unsaturated)
Observation: The purple colour of KMnO4 disappears
ethane (saturated)
Observation: The purple colour of KMnO4 remains
ii) Reaction of alkene with oxygen using a silver catalyst
produces epoxyethane.
H H H H
O2, Ag | |
C=C H-C – C–H

450 K
H H O epoxyethane
ethane H2O,
dilute H2SO4,
60 oC
H H
| |
H -C – C –H
| |
OH OH
(f) Polymerization
Alkenes may undergo addition polymerization reaction. For example, ethene
(monomer) forms polyethene (polymer).
Polymerisation of ethene may be initiated by a peroxide, RO-OR (free-

radical polymerisation) or by Ziegler catalyst (a mixture of titanium
tetrachloride, TiCl4, and triethyl aluminium, (CH3CH2)3Al).
Chemical Test
• Baeyer’s Test
• Bromine test
• Chemical test is a simple experiment to distinguish between

organic compounds.
• The test should have a significant observation.

Baeyer’s test
• Reagent : KMnO4 (basic)

• Observation: purple colour of solution will be decolorized.
H OH-
H H
H
+ KMnO4
C C cold H C C H
purple
H H
OH OH
colourless
CHARACTERIZATION TEST : Bromine test
Reagent : Br2 in CCl4
• Hydrocarbons are colourless liquid. Bromine dissolved in

CCl4 solvent forms an orange / brown solution.

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Alkenes

Saturated compounds (alkanes):

• Containing double bond are alkenes.

sp2 hybridization => flat, 120o bond angles

σ bond & π bond => H2C=CH2

No rotation about double bond!

Alkanes contain single bonds only -ANE ending

Alkenes contain a double bond -ENE ending

Alkynes contain a triple bond between -YNE ending

Parent Name = longest continuous chain of carbon atoms

Use Greek prefixes to indicate the presence of multiple

• IUPAC nomenclature rules for alkenes and alkynes are similar to

• Step 1. Name the parent compound. Find the longest chain

• Step 3: Assign numbers and names to the branching substituents,

• Step 5. Assemble the name

 For example, in the dehydration of 2-butanol, 2-butene (the

In the presence of hydrogen / organic peroxides (RO-OR), alkenes

This reaction, known as Baeyer test, may be used to distinguish

C=C H-C – C–H

Polymerisation of ethene may be initiated by a peroxide, RO-OR (free-

• Chemical test is a simple experiment to distinguish between

• The test should have a significant observation.

• Reagent : KMnO4 (basic)

• Hydrocarbons are colourless liquid. Bromine dissolved in

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