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ELECTROPHILIC ADDITION

Alkenes are susceptible to attack by

electrophiles (lone pair acceptors).

This is because the C=C double bond is very electron rich due to the electron cloud of the  bond.

In an addition reaction, the C=C double bond opens up and an atom or group of atoms joins onto each C of the C=C double bond.

During the mechanism, a carbocation is formed. Where more than one carbocation can be formed, the main product will be formed from the more stable carbocation. In general:

 tertiary >secondary >primary carbocationcarbocationcarbocation

most stableleast stable

ELECTROPHILIC ADDITION 1 – reaction with Br2

Reagent

Br2

Conditions

aqueous (i.e. bromine water)

What happens

C=C opens up; added onto the two C atoms of the C=C double bond:Br & Br

Overall equation

+ Br2

Mechanism

electrophilic addition

:Br-

Example 1

e.g. propene + Br2

+ Br2

electrophilic addition

+

Br2

ELECTROPHILIC ADDITION 2 – reaction with HBr

Reagent

HBr

Conditions

What happens

C=C opens up; added onto the two C atoms of the C=C double bond:H & Br

Overall equation

+ HBr

Mechanism

electrophilic addition

:

Br-

Example 3

e.g. propene + HBr

electrophilic addition

+ HBr

:Br-

Main product is formed from the 2 carbocation

that is more stable than alternative 1 carbocation that

produces

from

Example 4

e.g. methylpropene + H

Br

+ HBr

Main product is formed from the 3 carbocation that is more stable than alternative 1 carbocation that

electrophilic addition

:Br-

produces

from

ELECTROPHILIC ADDITION 3 – reaction with H2SO4

ReagentH2SO4

ConditionsConcentrated H2SO4

What happens

C=C opens up; added onto the two C atoms of the C=C double bond: H & O-SO2OH

Overall equation

+ H2SO4

Mechanism

electrophilic

addition

Example 5e.g. methylpropene + conc H2SO4

+ H2SO4

electrophilic

addition

Main product is formed from the 3 carbocation that is more stable than alternative 1 carbocation that

producesfrom

Example 6e.g. but-1-ene + conc H2SO4+ H SO

2 4

electrophilic

addition

Main product is formed from the 3 carbocation that is more stable than alternative 1 carbocation that

producesfrom



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