CHEN 2231
Organic Chemistry
Sulaiman Al-Isaee
Department of Engineering
College of Applied
Sciences-Suhar
Chapter 3: Alkenes and Alkynes
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Hydrogenation of Alkenes and Alkynes
Hydrocarbons that have carbon-carbon double bond are called alkenes;
those with a carbon-carbon triple bond are alkynes
Their general formulas are CnH2n alkenes and CnH2n-2 alkynes
Both alkenes and alkynes are unsaturated hydrocarbons
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Compounds with more than one double or triple bonds exist. Multiple
double bonds may lead to dienes, trienes, tetraenes and polyenes. β-
carotene and lycopene are examples of polyenes
When two or more multiple bonds re present in a molecule, they can be
classified depending on the relative positions of the bonds
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Which of the following compounds have conjugated multiple
bonds?
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Nomenclature
1. The ending –ene is used to designate carbon-carbon double bond.
When more than one double bond is present, the ending is –diene,
triene, tetraene and so on. The ending –yne is used for triple
carbon-carbon bond.
2. Select the longest chain that includes both carbons of the double
bond or triple bond.
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Number the chain from the end nearest the multiple bond so that the carbon
atoms in that bond have the lowest possible numbers.
If the multiple bond is equidistant from both ends of the chain, number the
chain from the end nearest the first branch point.
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Indicate the position of the multiple bond using the lower numbered
carbon atom of that bond.
If more than one multiple bond is present, number the chain from the
end nearest the first multiple bond.
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If the double bond and the triple bond are equidistant from the end of
the chain, the double bond receives the lowest number.
The root name is from the longest carbon chain containing the
multiple bond
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The numbering rules applied
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With the cyclic hydrocarbons, we start numbering the ring with the
carbons of the multiple bond.
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Write the structural formula for
3-methyl-2-pentene
1,4-dichloro-2-pentene
3-hexyne
1,2-dimethylcyclobutene
2-bromo-1,3-pentadiene
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Some Common names
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Some Facts about Double Bonds
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The Orbital Model of a Double Bond; the pi Bond
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Cis-Trans Isomerism in Alkenes
Because rotation at carbon–carbon double bonds is
restricted, cis–trans isomerism (geometric isomerism)
is possible in appropriately substituted alkenes.
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Are cis-trans isomers possible for 1-butene and 2-butene?
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Geometric isomers of alkenes can be interconverted if sufficient energy is
supplied to break the pi bond and allow rotation about the remaining sigma
bond.
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Addition and Substitution Reactions Compared
Addition of halogens X2
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Addition of Water (Hydration)
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Addition of Acids
Acids that add this way are the hydrogen halides (H-F, H-Cl, H-Br, H-I)
and sulfuric acid (H-OSO3H)
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Write the equation for each of the following reactions
a) 2-butene + HCl
b) 3-Hexene + HI
c) 4-methylcyclopentene + HBr
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Addition of Unsymmetric Reagents to Unsymmetric
Alkenes; Markovnikov’s Rule
100 years ago: When an unsymmetric reagent adds to an
unsymmetric alkene, the electropositive part of the reagent
bonds to the carbon of the double bond that has the greater
number of hydrogen atoms attached to it.
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Mechanism of Electrophilic Addition to Alkenes
Electrophiles (literally, electron lovers) are electron-poor
reagents; in reactions they seek electrons.
They are often positive ions (cations) or otherwise
electron-deficient species.
Nucleophiles (literally, nucleus lovers), on the other
hand, are electron rich; they form bonds by donating
electrons to an electrophile.
Mechanism of Electrophilic Addition to
Alkenes
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Markovnokov’s Rule Explained
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Reaction Equilibrium
What determines whether a reaction will proceed to the right,
toward products?
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Reaction Rates: How Fast Does a Reaction Go?
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Let us see how reaction rates are related to Markovnikov’s Rule.
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Hydroboration of Alkenes
Hydroboration was discovered by Professor Herbert C.
Brown (1912–2004).
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Thus, it resembles a normal electrophilic addition to an alkene,
following Markovnikov’s Rule, even though the addition is
concerted (that is, all bond-breaking and bond- making
occur in one step).
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The trialkylboranes made in this way are usually not isolated but are
treated with some other reagent to obtain the desired final product.
For example, trialkylboranes can be oxidized by hydrogen peroxide
and base to give alcohols.
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What alkene is needed to obtain he alcohol below via hydroboration-oxidation
sequence, what product would this alkene give with acid-catalyzed hydration.
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Addition of Hydrogen
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Addition to Conjugated Systems
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Cycloaddition to Conjugated Dienes: Diels-Alder Reaction
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Free-Radical Additions; Polyethene
A polymer is a large molecule, usually with a high molecular
weight, built up from small repeating units.
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Oxidation with permanganate; a Chemical Test
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Ozonolysis of Alkenes
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Other Alkene Oxidations
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