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Electrophilic addition

 

 
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Electrophilic addition
 
 
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In organic chemistry
Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
, an electrophilic addition reaction is an addition reaction
Addition reaction

An addition reaction, in organic chemistry, is in its simplest terms an organic reaction where two or more molecules combine to form a larger one....
 where, in a chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
, a pi bond
Pi bond

In chemistry, pi bonds are covalent bond chemical bonds where two lobes of one involved electron atomic orbital overlap two lobes of the other involved electron orbital....
 is removed by the creation of two new covalent bond
Covalent bond

A covalent bond is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms, or between atoms and other covalent bonds....
s. The substrate of an electrophilic addition reaction must have a double bond or triple bond .

The driving force for this reaction is the formation of an electrophile
Electrophile

In chemistry, an electrophile is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to Chemical bond to a nucleophile....
 X+ that forms a covalent bond
Covalent bond

A covalent bond is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms, or between atoms and other covalent bonds....
 with an electron-rich unsaturated
Saturation (chemistry)

In chemistry, saturation has five different meanings:#In physical chemistry, saturation is the point at which a solution of a substance can dissolve no more of that substance and additional amounts of it will appear as a Precipitation ....
 C=C bond.






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In organic chemistry
Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
, an electrophilic addition reaction is an addition reaction
Addition reaction

An addition reaction, in organic chemistry, is in its simplest terms an organic reaction where two or more molecules combine to form a larger one....
 where, in a chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
, a pi bond
Pi bond

In chemistry, pi bonds are covalent bond chemical bonds where two lobes of one involved electron atomic orbital overlap two lobes of the other involved electron orbital....
 is removed by the creation of two new covalent bond
Covalent bond

A covalent bond is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms, or between atoms and other covalent bonds....
s. The substrate of an electrophilic addition reaction must have a double bond or triple bond .

The driving force for this reaction is the formation of an electrophile
Electrophile

In chemistry, an electrophile is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to Chemical bond to a nucleophile....
 X+ that forms a covalent bond
Covalent bond

A covalent bond is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms, or between atoms and other covalent bonds....
 with an electron-rich unsaturated
Saturation (chemistry)

In chemistry, saturation has five different meanings:#In physical chemistry, saturation is the point at which a solution of a substance can dissolve no more of that substance and additional amounts of it will appear as a Precipitation ....
 C=C bond. The positive charge on X is transferred to the carbon-carbon bond.

In step 2 of an electrophilic addition, the positively charged intermediate combines with (Y) that is electron-rich and usually an anion to form the second covalent bond.


Step 2 is the same nucleophilic attack process found in an SN1 reaction
SN1 reaction

The SN1 reaction is a substitution reaction in organic chemistry. "SN" stands for nucleophilic substitution and the "1" represents the fact that the rate-determining step is molecule....
. The exact nature of the electrophile and the nature of the positively charged intermediate are not always clear and depend on reactants and reaction conditions.

In all asymmetric addition reactions to carbon, regioselectivity
Regioselectivity

In chemistry, regioselectivity is the preference of one direction of chemical bond making or breaking over all other possible directions . It can often apply to which of many possible positions a reagent will affect, such as which proton a strong Base will abstract from an organic molecule, or where on a substituted benzene ring a further s...
 is important and often determined by Markovnikov's rule
Markovnikov's rule

In organic chemistry, Markovnikov's rule or Markownikoff's rule is an observation based on Zaitsev's rule. It was formulated by the Russian chemist Vladimir Vasilevich Markovnikov in 1870 ....
. Organoborane
Organoborane

Organoborane or organoboron compounds are chemical compounds that are organic derivatives of BH3, for example trialkyl boranes....
 compounds give anti-Markovnikov additions. Electrophilic attack to an aromatic system results in electrophilic aromatic substitution
Electrophilic aromatic substitution

Electrophilic aromatic substitution or EAS is an organic reaction in which an atom, usually hydrogen, appended to an aromatic ring is replaced by an electrophile....
 rather than an addition reaction.

Typical electrophilic additions

Typical electrophilic additions to alkenes with reagents are:
  • dihalo addition reactions: X2
  • Hydrohalogenation
    Hydrohalogenation

    A hydrohalogenation reaction is the electrophilic addition of hydrohalic acids like hydrogen chloride or hydrogen bromide to alkenes to yield the corresponding haloalkanes ....
    s:HX
  • Hydration reaction
    Hydration reaction

    In organic chemistry, a hydration reaction is a chemical reaction in which a hydroxyl group and a hydrogen cation are added to the two carbon atoms covalent bonded together in the carbon-carbon double bond which makes up an alkene functional group....
    s: H2O
  • Hydrogenation
    Hydrogenation

    Hydrogenation is the chemical reaction that results from the addition of hydrogen . The process is usually employed to a redox or Saturation organic compounds....
    s H2
  • Oxymercuration reaction
    Oxymercuration reaction

    The oxymercuration reaction is an electrophilic addition organic reaction that transforms an alkene into a neutral alcohol. In oxymercuration, the alkene reacts with mercuric acetate in aqueous solution to yield the addition of an acetoxymercuri group and a hydroxy group across the double bond....
    s: mercuric acetate, water
  • Hydroboration-oxidation reaction
    Hydroboration-oxidation reaction

    In organic chemistry, the hydroboration-oxidation reaction is a two-step organic reaction that converts an alkene into a neutral alcohol by the net addition of water across the double bond....
    s : diborane
  • the Prins reaction
    Prins reaction

    The Prins reaction is an organic reaction consisting of an electrophilic addition of an aldehyde or ketone to an alkene or alkyne followed by capture of a nucleophile ....
     : formaldehyde, water