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Alkenes

The document discusses the structure, nomenclature, and reactions of alkenes. It defines alkenes and elements of unsaturation. It describes naming alkenes and cycloalkenes and discusses E/Z nomenclature. Several reactions for alkene synthesis and functionalization are also outlined.

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Lizeth Aguirre Martinez
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11 views21 pages

Alkenes

The document discusses the structure, nomenclature, and reactions of alkenes. It defines alkenes and elements of unsaturation. It describes naming alkenes and cycloalkenes and discusses E/Z nomenclature. Several reactions for alkene synthesis and functionalization are also outlined.

Uploaded by

Lizeth Aguirre Martinez
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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Título: Structure

and Synthesis
of Alkenes
Dra. Esdrey Rodríguez Cárdenas
Alquenos
Alkenes are sometimes called olefins. CnH2n

Elements of Unsaturation in Hydrocarbons


The presence of a pi bond of an alkene (or an
alkyne) or the ring of a cyclic compound
decreases the number of hydrogen atoms in a
molecular formula. These structural features are
called elements of unsaturation.*
Each element of unsaturation corresponds to two
fewer hydrogen atoms than in the “saturated”
formula.
Nomenclature of Alkenes
Name the parent hydrocarbon.Find the longest carbon chain
that contains the double bond, and name the compound using
the suffi x -ene in place of -ane

Number the carbon atoms in the chain.


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

Write the full name.


Number the substituents on the main chain according to their
position, and list them alphabetically. Indicate the position of
the double bond by giving the number of the first alkene
carbon and placing that number directly before the -ene suffix.
If more than one double bond is present, give the position of
each and use the appropriate multiplier suffix -diene, -triene,
-tetraene, and soon.
Nomenclatura de Alquenos
Cycloalkenes are named similarly, but because there is no chain end to
begin from, we number the cycloalkene so that the double bond is
between C1 and C2 and the fi rst substituent has as low a number as
possible.

Note also that =CH2 substituent is called a methylene group, a H2C=CH- substituent is called a vinyl
group, and a H2C=CHCH2- substituent is called an allyl group
Ejercicios
• If the higher-priority groups
on each carbon are on the
same side of the double
bond, the alkene is
designated Z, for the
German zusammen,
meaning “together.”
• If the higher-priority groups are on opposite sides, the
alkene is designated E, for the German entgegen,
meaning “opposite.” (A simple way to remember which
is which is to note that the groups are on “ze zame zide”
in the Z isomer.)
1. Considering the double-bond carbons separately, look at the two atoms directly
attached to each and rank them according to atomic number.

2. If a decision can’t be reached by ranking the first atoms in the substituent, look at the
second, third, or fourth atoms away from the double-bond carbons until the first difference is
found.

3. Multiple-bonded atoms are equivalent to the same number of


singlebonded atoms.
Ejercicios
Reactions and Methods for Synthesis of Alkenes
Electrophylic addition:
Addition of Halogens to Alkenes Acid-catalyzed hydration

MARKOVNIKOV’S RULE: The addition of a proton


acid to the double bond of an alkene results in a
product with the acid proton bonded to the carbon
atom that already holds the greater number of
hydrogen atoms. In an electrophilic addition to an alkene,
the electrophile adds in such a way as to generate the most
stable intermediate.
Oxymercuration–demercuration
Alkoxymercuration–demercuration

Hydroboration–oxidation
Polymerization
Addition of Carbenes: Cyclopropanation
Reduction: Catalytic Hydrogenation

Oxidative Additions: Addition of halogens


Oxidative Additions: Halohydrin formation Oxidative Additions: Anti dihydroxylation

Oxidative Additions: Epoxidation

Oxidative Additions: Syn dihydroxylation


Oxidative Cleavage of Alkenes:Ozonolysis
Olefin (Alkene) Metathesis

Oxidative Cleavage of Alkenes: Potassium permanganate


➢ Dehydrohalogenation of alkyl halides ➢ Dehalogenation of vicinal dibromides

➢ Dehydration of alcohols ➢ Dehydrogenation of alkanes


➢ Hofmann and Cope eliminations ➢ Reduction of alkynes

➢ Wittig reaction
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