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Addition Reactions of Alkenes

1) Addition reactions involve adding atoms or groups of atoms to a double or triple bond. Common addition reactions for alkenes include hydrogenation, halogenation, hydration, and hydrohalogenation. 2) Hydrogenation of alkenes adds hydrogen across the double bond to form an alkane. Halogenation adds bromine or chlorine. Hydration adds water to form an alcohol. Hydrohalogenation adds hydrogen halides like HCl or HBr. 3) Alkyne addition reactions are similar to alkene reactions. Halogenation and hydrohalogenation add across the triple bond. Hydrogenation of alkynes forms an alkene then alkane, but

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433 views32 pages

Addition Reactions of Alkenes

1) Addition reactions involve adding atoms or groups of atoms to a double or triple bond. Common addition reactions for alkenes include hydrogenation, halogenation, hydration, and hydrohalogenation. 2) Hydrogenation of alkenes adds hydrogen across the double bond to form an alkane. Halogenation adds bromine or chlorine. Hydration adds water to form an alcohol. Hydrohalogenation adds hydrogen halides like HCl or HBr. 3) Alkyne addition reactions are similar to alkene reactions. Halogenation and hydrohalogenation add across the triple bond. Hydrogenation of alkynes forms an alkene then alkane, but

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Lalitha Kurumanghat
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Addition Reactions

Involving
Alkenes and Alkynes
Addition Reaction
 Addition of two atoms or groups of atoms to a
double bond.
R
R R

A R C A
+
B R C B

R R
R

 R can be carbon or hydrogen.


Types of Addition Reactions
 The major alkene addition reactions include
 Addition of hydrogen (H2) – hydrogenation
 Addition of halogens (Cl2 or Br2) –
halogenation
 Addition of water (H2O) – hydration
 Addition of hydrogen halides (HBr or HCl) –
hydrohalogenation
 Note: Double bond becomes a single bond.
Hydrogenation: Adding H2
R
R R

H Pt, Pd, or Ni R C H
+
H heat or pressure R C H

R R
R
 Double bond is broken
 H atom added to both sides of double bond
 Platinum, palladium, or nickel catalyst required
 Heat and/or pressure may also be needed
Examples of Hydrogenation
 Hydrogenation of 1-propene to propane
H CH3 H H
Pd
C C + H H H C C CH3
H H
H H

 Hydrogenation of trans-2-butene
H H
H CH3
Pd
C C + H H H3C C C CH3
H3C H
H H
YOU TRY THESE!
 Write hydrogenation reactions for:
 1-butene
 2-methyl-2-butene
 ethene
 1-hexene
Answer:
Halogenation: Adding Br2 or Cl2

R
R R

Br R C Br
+
Br R C Br

R R
R

 This reaction occurs easily and does not


require a catalyst.
Examples of Halogenation
 Bromination of 1-propene to form 1,2-
dibromopropane
H CH3 Br Br
C C + Br Br H C C CH3
H H
H H

 Chlorination of trans-2-butene to form 2,3-


dichlorobutane
Cl Cl
H CH3
C C + Cl Cl H3C C C CH3
H3C H
H H
YOU TRY THESE!
 Write halogenation reactions for:
 1-pentene with bromine
 2-methyl-2-butene with chlorine
 Ethene with chlorine
 1-hexene with iodine
Answer:
Hydration: Addition of H2O
R
R R

H R C H
+
OH R C OH

R R
R

 Requires a trace of acid (H+) as a catalyst


 The product is an alcohol
 Markovnikov’s rule applies
Markovnikov’s Rule
 A mixture of products is formed when an
unsymmetrical alkene is hydrated.
 One product is always favored over the other.
 Vladimir Markovnikov came up with a rule to
determine the major product formed.
 When HX adds across an asymmetric double bond,
the major product formed is the molecule in which
hydrogen adds to the carbon atom in the double bond
with the grater number of hydrogen atoms already
attached.
 “The rich get richer.”
Example of Markovnikov’s Rule
H OH

H C C CH3
H CH3
H+ H H
C C + H OH
Major product
H H
OH H

H C C CH3

H H

Minor product

 Hydration of 1-propene to form 2-propanol


(major) and 1-propanol (minor)
YOU TRY THESE!
 Write the hydration equation for each of the
following molecules. Indicate the major and
minor products for the reactions where
applicable.
 1-pentene
 2-methyl-2-butene
 ethene
Answer:
Hydrohalogenation: Adding HCl or
HBr

R
R R

H R C H
+
Cl R C Cl

R R
R

 Follows Markovnikov’s rule


Examples of Hydrohalogenation
H Br

H C C CH3
H CH3
H H
C C + H Br
Major product
H H
Br H

H C C CH3

H H

Minor product
 Hydrobromination of 1-propene to form 2-
bromopropane (major) and 1-bromopropane
(minor)
YOU TRY THESE!
 Write the hydrohalogenation equation for
each of the following molecules. Indicate the
major and minor products for the reactions
where applicable.
 1-pentene with HCl
 2-methyl-2-butene with HBr
 2-methyl-2-butene with HCl
 Ethene with HCl
Answer:
Answer:
ADDITION REATIONS
IN
ALKYNES
Hydrogenation of Alkynes
 Alkynes react twice with hydrogen when a
metal catalyst is present. The alkene is
formed first, and then the alkane.
LINDLAR CATALYST
 There is a special deactivated catalyst, Lindlar, that
allows the hydrogenation of an alkyne to stop at the
alkene, after the addition of only one mole of
hydrogen.
 Lindlar is a palladium catalyst, where the palladium is
precipitated onto particles of barium sulfate from a
solution which has quinolone present.

Lindlar
With Lindlar catalyst, only one mole of hydrogen will add to an
alkyne. As with other catalysts, hydrogenations with Lindlar are syn
stereospecific additions.
Alkyne Addition
 Halogens add across triple bonds in the same
way as across double bonds.

Both additions proceed


through a bridged
intermediate and both
additions are
stereospecific anti.
YOU TRY THESE!

 Write halogenation reactions for:


 propyne with chlorine
 2-butyne with chlorine
 pentyne with with iodine
Answer:
Answer:
Alkyne Addition
 Hydrohalogen addition across triple bonds is
also similar to addition across double bonds.
Addition follows Markovnikov’s rule.

Br H Br H
H Br H Br
CH3 C CH CH3 C CH CH3 C CH
CCl4 CCl4
Br H
YOU TRY THESE!
 Write the hydrohalogenation equation for
each of the following molecules.
 propyne with HCl
 2-butyne with HCl
 pentyne with with HI
Answer:

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