ADDITION REACTION
Represented By:Group 6
Saira-028,Maham,Kinza,Hafifa,Nida,Arooj-
066
Represnted To: Ms. Uswa
Table of Content
Introduction
Types of Addition Reaction
Electrophilic Addition Reaction(Mechanism)
Nucleophilic Addition Reaction(Mechanism)
Markovnikov Rule
Ozonolysis of Alkenes(Mechanism)
Factors Associated with Alkenes
Reaction of Alkynes
INTRODUCTION
• Reactions which involve the combination of two reacting
molecules to give single molecule of product.
A+B C
(product)
• These are limited to chemical compounds with multiple
bonds.
• Alkenes mostly take part in addition reactions.
• The π-bond is broken and two new σ-bonds are formed.
• Alkenes are electron rich, with elctron density of π-bond
concentrated above and below.
• Addition reactions to alkenes and alkynes are sometimes
called saturation reactions.
• Addition reactions are the reverse of elimination reactions.
TYPES OF ADDITION REACTION
POLAR ADDITION REACTIONS
Electrophile Addition
• The process of adding an
electrophile to the pi bond
of an alkene.
• An electrophile forms a
sigma bond with a vinyl
carbon atom in double
bond.
Nucleophile Addition
• The process of adding a
nucleophile to either an
electron-deficient species
or pi bond in a molecule.
• A nucleophile forms a
sigma bond with a carbon
atom in the substrate.
Example of Electrophilic Example of Nucleophilic
NON POLAR ADDITION REACTION
Free Radical Addition
• The addition reaction which
involves free radical.
• The reaction occurs
between a radical and a
non-radical.
• It may involve two radicals.
• It is also known as radical
chain mechanism.
Cyclo Addition
• The reaction in which two
or more unsaturated
molecules combine.
• It forms a cyclic
adduct(cyclization).
• There is net reduction of
bond multiplicity.
• It permits carbon-carbon
without nucleophile or
electrophile.
Example of Free Radical Addition
Chlorination of
Methane
• A reaction between
methane and chlorine in
the prsence of UV light.
• A product of
chloromethane is
produced.
CH₄+Cl₂→CH₃Cl+HCl
Mechanism
1.Chain initiation:
Cl2 → 2Cl·
2.Chain propagation reactions :
CH4 + Cl·→CH·3+ HCl
CH·3 + Cl2→CH3Cl + Cl·
3.Chain termination reactions:
2Cl·→Cl2
CH·3 + Cl· → CH3C l
Example of
Cyclo
addition
Diels-Alder reaction
• A reaction between a conjugated
diene and a substituted
alkene(dienophile).
• A substituted cyclohexene
derivative is formed.
Electrophilic Addition
• The addition of an electrophile to a pi bond of an alkene.
• The carbon-carbon in an alkene is a region of high
electron density.
• This makes the C=C bond attractive to electrophiles.
• This is an electrophile addition reaction.
.
Mechanism
• It is a two step mechanism ,
Step 1:
• H-Br undergoes hetrolytic bond fission.
• The proton (H+) bonds with the caarbon atom of the C=C.
• A carbocation intermediate is formed.
Step 2:
• The anion uses a lone pair of electrons to form a bond
with the carbocation.
• The bromide ion forms a bond with the carbocation
producing bromoethane.
Nucleopilic Addition Reaction
• A nucleophile forms a single bond with an electron
defficient species.
• The conversion of carbonyl groups into variety of
functional groups.
Mechanism The electrophilic carbonyl
carbon forms a sigma bond
with the nucleophile.
The carbon-oxygen pi bond
is broken, forming an
alkoxide intermediate.
The subsequent protonation
of the alkoxide yields the
alcohol derivative.
Generally,
these
reactions are
broken down
into three
steps:
Addition of HCN
• Aldehydes and ketones undergo reaction with HCN to
produce cyanohydrins.
• The reaction progresses very slowly by using pure
hydrogen cyanide.
• The catalyst helps to speed up the reaction.
• As catalysis helps in the generation of cyanide ion (CN)
which acts as a stronger nucleophile.
MECHANISM
• The polar nature of the C=O bond makes the carbonyl
carbon electrophilic in nature.
• The CN¯ executes a nucleophilic attack on the carbonyl
carbon, resulting in the formation of an intermediate.
• This intermediate is now protonated to afford the
cyanohydrin product.
MARKOVNIKOV RULE
• Hydrogen is added to the carbon with the most hydrogens
and the halide is added to the carbon with least
hydrogens.
• the addition of hydrobromic acid (HBr) to propene;
• The majority of the products formed obey Markovnikov’s
rule, whereas the minority of the products do not.
Step 1:
• The alkene is protonated and it gives rise to the more
stable carbocation as
• Two types of carbocations that can be formed by
protonation,
Primary
Secondary(more stable and preferred)
Step 2:
• The halide ion nucleophile now attacks the carbocation.
• The reaction yields the alkyl halide.
• Rule was developed for its application in the addition
reaction of hydrogen halides to alkenes.
• The opposite to this is anti-Markovnikov rule.
Ozonolysis of Alkene
• Ozonolysis implies that ozone causes the alkene to break.
• a method of oxidatively cleaving alkenes using ozone
(O3), a reactive allotrope of oxygen.
• The process allows for carbon-carbon double or triple
bonds to be replaced by double bonds with oxygen.
Mechanism of Ozonolysis
• Step 1:
• The π electrons act as the
nucleophile, attacking the
ozone at the electrophilic
terminal O. A second C-O is
formed by the nucleophilic O
attacking the other end of
the C=C.
• Step 2:
The cyclic species called the
malozonide rearranges to the
ozonide.
• Step 3:
The ozonide decomposes
on work-up. Reductive work-
up with (usually Zn / acetic
acid) gives the two carbonyl
groups.
ADDITION REACTIONS OF ALKYNES
• The principal reaction of the alkynes is addition across
the triple bond to form alkanes.
• These addition reactions are analogous to those of the
alkenes.
HYDROGENTION
HALOGENATION
HYDROHALOGENATION
HYDRATION
Hydrogenation
• Alkynes undergo catalytic
hydrogenation with the some
catalyst(Pt, Pd, Lindlar’s
catalyst).
• In a stepwise manner an
alkenes is formed first and then
alkane.
Halogenation
• The addition of halogens to an
alkyne proceeds in the stepwise
manner.
• the formation of alkene, which
undergoes further reaction to a
tetrahaloalkane.
Hydrohalogenation
• Hydrogen halides react with
alkynes in the same manner as
they do with alkenes.
• Both steps in the above addition
follow the Markovnikov rule.
Hydration
• The addition of the elements of
water across the triple bond of
an alkyne leads to the formation
of aldehydes and ketones.
• terminal alkyne aldehyde
• non-terminal alkyne ketone
REFERENCES
1. Morrison, R. T.; Boyd, R. N. (1983). Organic
Chemistry(4th ed.). Boston: Allyn and Bacon.
2. March, Jerry; (1985). Advanced Organic Chemistry
reactions, mechanisms and structure (3rd ed.). New York:
John Wiley & Sons.
3. Fleming, Ian (2010). Molecular orbitals and organic chemical
reactions. New York: Wiley.
4. Myles W. Smith; Phil S. Baran (2015-08-28). "As simple as
[2+2]". Science 349 (6251): 925–926.
5. Hein, Sara M. (June 2006). "An Exploration of a
Photochemical Pericyclic Reaction Using NMR
Data". Journal of Chemical Education. 83 (6): 940–942.
THANK YOU

Addition Reaction.pptx

  • 1.
    ADDITION REACTION Represented By:Group6 Saira-028,Maham,Kinza,Hafifa,Nida,Arooj- 066 Represnted To: Ms. Uswa
  • 2.
    Table of Content Introduction Typesof Addition Reaction Electrophilic Addition Reaction(Mechanism) Nucleophilic Addition Reaction(Mechanism) Markovnikov Rule Ozonolysis of Alkenes(Mechanism) Factors Associated with Alkenes Reaction of Alkynes
  • 3.
    INTRODUCTION • Reactions whichinvolve the combination of two reacting molecules to give single molecule of product. A+B C (product) • These are limited to chemical compounds with multiple bonds.
  • 4.
    • Alkenes mostlytake part in addition reactions. • The π-bond is broken and two new σ-bonds are formed. • Alkenes are electron rich, with elctron density of π-bond concentrated above and below.
  • 5.
    • Addition reactionsto alkenes and alkynes are sometimes called saturation reactions. • Addition reactions are the reverse of elimination reactions.
  • 6.
  • 7.
    POLAR ADDITION REACTIONS ElectrophileAddition • The process of adding an electrophile to the pi bond of an alkene. • An electrophile forms a sigma bond with a vinyl carbon atom in double bond. Nucleophile Addition • The process of adding a nucleophile to either an electron-deficient species or pi bond in a molecule. • A nucleophile forms a sigma bond with a carbon atom in the substrate.
  • 8.
    Example of ElectrophilicExample of Nucleophilic
  • 9.
    NON POLAR ADDITIONREACTION Free Radical Addition • The addition reaction which involves free radical. • The reaction occurs between a radical and a non-radical. • It may involve two radicals. • It is also known as radical chain mechanism. Cyclo Addition • The reaction in which two or more unsaturated molecules combine. • It forms a cyclic adduct(cyclization). • There is net reduction of bond multiplicity. • It permits carbon-carbon without nucleophile or electrophile.
  • 10.
    Example of FreeRadical Addition Chlorination of Methane • A reaction between methane and chlorine in the prsence of UV light. • A product of chloromethane is produced. CH₄+Cl₂→CH₃Cl+HCl Mechanism 1.Chain initiation: Cl2 → 2Cl· 2.Chain propagation reactions : CH4 + Cl·→CH·3+ HCl CH·3 + Cl2→CH3Cl + Cl· 3.Chain termination reactions: 2Cl·→Cl2 CH·3 + Cl· → CH3C l
  • 11.
    Example of Cyclo addition Diels-Alder reaction •A reaction between a conjugated diene and a substituted alkene(dienophile). • A substituted cyclohexene derivative is formed.
  • 12.
    Electrophilic Addition • Theaddition of an electrophile to a pi bond of an alkene. • The carbon-carbon in an alkene is a region of high electron density. • This makes the C=C bond attractive to electrophiles. • This is an electrophile addition reaction. .
  • 13.
    Mechanism • It isa two step mechanism , Step 1: • H-Br undergoes hetrolytic bond fission. • The proton (H+) bonds with the caarbon atom of the C=C. • A carbocation intermediate is formed.
  • 14.
    Step 2: • Theanion uses a lone pair of electrons to form a bond with the carbocation. • The bromide ion forms a bond with the carbocation producing bromoethane.
  • 15.
    Nucleopilic Addition Reaction •A nucleophile forms a single bond with an electron defficient species. • The conversion of carbonyl groups into variety of functional groups.
  • 16.
    Mechanism The electrophiliccarbonyl carbon forms a sigma bond with the nucleophile. The carbon-oxygen pi bond is broken, forming an alkoxide intermediate. The subsequent protonation of the alkoxide yields the alcohol derivative. Generally, these reactions are broken down into three steps:
  • 17.
    Addition of HCN •Aldehydes and ketones undergo reaction with HCN to produce cyanohydrins. • The reaction progresses very slowly by using pure hydrogen cyanide. • The catalyst helps to speed up the reaction. • As catalysis helps in the generation of cyanide ion (CN) which acts as a stronger nucleophile.
  • 18.
    MECHANISM • The polarnature of the C=O bond makes the carbonyl carbon electrophilic in nature. • The CN¯ executes a nucleophilic attack on the carbonyl carbon, resulting in the formation of an intermediate. • This intermediate is now protonated to afford the cyanohydrin product.
  • 19.
    MARKOVNIKOV RULE • Hydrogenis added to the carbon with the most hydrogens and the halide is added to the carbon with least hydrogens. • the addition of hydrobromic acid (HBr) to propene; • The majority of the products formed obey Markovnikov’s rule, whereas the minority of the products do not.
  • 20.
    Step 1: • Thealkene is protonated and it gives rise to the more stable carbocation as • Two types of carbocations that can be formed by protonation, Primary Secondary(more stable and preferred)
  • 21.
    Step 2: • Thehalide ion nucleophile now attacks the carbocation. • The reaction yields the alkyl halide. • Rule was developed for its application in the addition reaction of hydrogen halides to alkenes. • The opposite to this is anti-Markovnikov rule.
  • 22.
    Ozonolysis of Alkene •Ozonolysis implies that ozone causes the alkene to break. • a method of oxidatively cleaving alkenes using ozone (O3), a reactive allotrope of oxygen. • The process allows for carbon-carbon double or triple bonds to be replaced by double bonds with oxygen.
  • 23.
    Mechanism of Ozonolysis •Step 1: • The π electrons act as the nucleophile, attacking the ozone at the electrophilic terminal O. A second C-O is formed by the nucleophilic O attacking the other end of the C=C.
  • 24.
    • Step 2: Thecyclic species called the malozonide rearranges to the ozonide. • Step 3: The ozonide decomposes on work-up. Reductive work- up with (usually Zn / acetic acid) gives the two carbonyl groups.
  • 25.
    ADDITION REACTIONS OFALKYNES • The principal reaction of the alkynes is addition across the triple bond to form alkanes. • These addition reactions are analogous to those of the alkenes. HYDROGENTION HALOGENATION HYDROHALOGENATION HYDRATION
  • 26.
    Hydrogenation • Alkynes undergocatalytic hydrogenation with the some catalyst(Pt, Pd, Lindlar’s catalyst). • In a stepwise manner an alkenes is formed first and then alkane. Halogenation • The addition of halogens to an alkyne proceeds in the stepwise manner. • the formation of alkene, which undergoes further reaction to a tetrahaloalkane.
  • 27.
    Hydrohalogenation • Hydrogen halidesreact with alkynes in the same manner as they do with alkenes. • Both steps in the above addition follow the Markovnikov rule. Hydration • The addition of the elements of water across the triple bond of an alkyne leads to the formation of aldehydes and ketones. • terminal alkyne aldehyde • non-terminal alkyne ketone
  • 28.
    REFERENCES 1. Morrison, R.T.; Boyd, R. N. (1983). Organic Chemistry(4th ed.). Boston: Allyn and Bacon. 2. March, Jerry; (1985). Advanced Organic Chemistry reactions, mechanisms and structure (3rd ed.). New York: John Wiley & Sons. 3. Fleming, Ian (2010). Molecular orbitals and organic chemical reactions. New York: Wiley. 4. Myles W. Smith; Phil S. Baran (2015-08-28). "As simple as [2+2]". Science 349 (6251): 925–926. 5. Hein, Sara M. (June 2006). "An Exploration of a Photochemical Pericyclic Reaction Using NMR Data". Journal of Chemical Education. 83 (6): 940–942.
  • 29.