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PRESENTATION

ON
ADDITION TO CARBON-CARBON
MULTIPLE BOND

GUIDED BY- PRESENTED BY-


DR. ASTHANA LALCHAND
MAM SAHU
M.Sc. -1st SEM.
GOVT. V. Y. T. P.G. AUTO. COLLEGE DURG (C.G.)
CONTENT
Introduction
Types of addition reaction
Electrophilic addition
Nucleophilic addition
Free radical addition
References
INTRODUCTION
 In organic reaction, an unsaturated molecule and another
reagent combine to give saturated compound is called
addition reaction.

 In addition reaction the sp²-hybrid or( sp- hybrid) carbon


atoms are rehybridised to sp³.
 An addition reaction is usually exothermic.
 Addition reaction is the characteristics of reaction of a pi-
bond.
TYPES OF ADDION REACTION
ELECTROPHILIC ADDITION
REACTION
 The addition reaction, in which an electrophile initiate the
process is called electrophilic addition reaction.

 Electrophile include positive electrophile such as proton,


neutral electrophile such as bromine and the Lewis acids ,
BFȝ and AlXȝ.
 The electrophile and pi- electron interact with each other
and form pi- complex.
MECHANISM
 Electrophilic addition reaction involves two steps:

Step 1.

Step 2.
Free energy diagram for Electrophilic
addition reaction
MARKOVNIKOV RULE
 This rule states that in an electrophilic addition reaction, the
positive part of the unsymmetric reagent becomes bonded to
the doubly bonded carbon atom which has more number of
hydrogen atoms.
 Example .

 Reaction that illustrate Markovnikov rule are said to be


Markovnikov additions.
ANTI-MARKOVNIKOV ADDITION
 Anti-Markovnikov addition is observed if the alkene bears
a powerful electron-withdrawing group attached directly
to the doubly bonded carbon.
SYN AND ANTI ADDITION
 syn addition- If Electrophile and Nucleophile enter from
the same side of the double bond, the addition will be syn .

 anti addition, if Electrophile and Nucleophile enter from


the opposite side of the double bond, the addition will be
anti (or trans).
EXAMPLE OF ELECTROPHILIC
ADDITION REACTION
 Addition of hydrogen halide.

 The reactivity of HX in this reaction is HI>HBr>HCl>HF.


 Rate = K [alkene][HX]
NUCLEOPHILIC ADDITION
REACTION
 The addition reaction, in which nucleophile initiates the
process, the reaction is termed as nucleophilic addition
reaction.

 Nucleophilic addition reaction is the reverse of E1cb


elimination.
 This reaction generally take place in polar solvents.
 The most important reaction of this category is the Micheal
addition reaction.
MICHAEL ADDITION
 Conjugate addition of enolate ion to α,β- unsaturated
carbonyl compounds in the presence of Base, is called
Michael addition.

 Step 1.

 Step 2.

 Step 3.
FREE RADICAL ADDITION
REACTION
 An addition reactions involving free radical is called Free
radical addition reaction.
 Radical, are electron-deficient species. Thus the radicals will
attack the pi-system of double bond of an alkene.

 Radical addition takes place in non-polar solvent.


 The mode of the addition reaction involves the general steps
for the radical reactions, i.e. initiation, chain propagation and
termination.
Hydrobromination

 The radical addition of HBr to a carbon-carbon double


bond occurs in the presence of UV light or a small
amount of initiators such aS dibenzoyl peroxide.
 HF, HCl and HI do not give this additon.
 when propene react with hydrogen bromide in the
presence of dibenzoyl peroxide , the product is 1-
bromopropane.
MECHANISM
 Initiation-

 Propagation-

 Termination-
REFERENCES
1. March Jerry(1985). “Advanced Organic Chemistry
reactions”, Addition to carbon-carbon multiple bond(3rd
ed.).New York : John Willey & Sons.

2. Singh Jagdamba and L.D.S.Yadav (2004),"Advanced


Organic Chemistry”, Addition to carbon-carbon multiple
bond(14th ed.).Educational publishers: Pragati Prakashan.

3. Source by Internet & wikipedia.