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A:B
+
A + B
Double-barbed arrow
is used to show movement
of an electron pair.
ions
A:B
A. + B .
radicals
Single-barbed arrow
is used to show movement
of a single electron.
Bond Heterolysis
Bond heterolysis typically is found with polar covalent bonds where
the intrinsic electronegativities promote polarization of the bonding
electrons.
Electrophile(cations)
A:B
+
A + B
Nucleophile(anions)
A:B
D+
+ A:B
A : B + D+
C:A + B
C donates an electron
pair in forming bond to A
as B departs as anion.
HomolysisCleavage
refertobreakingcovalentbondbetweensame/diffatomswith
smallelectronegativitydifference
formfreeradical, Cl,H,CH3
endothermicabsorbenergytobreakdownthecovalentbond
providedbysunlight(UVlight)/high
temperature
Example
OrganicReagents
Divideinto3group:
Electrophile
Nucleophile
Freeradical
Electrophile
means
Areagentwhichcanacceptanelectronpairinarxn
or
Amolecule/ionwhichiselectrondeficient(lowedensity)and
attacktheelectronrichspecies(highedensity)
arepositivechargedspecies
Nucleophile
means
Areagentwhichdonateanelectronpairinarxn
or
Amolecule/ionwhichiselectronrichandattacktheelectron
deficientcentre
arenegativelychargedoraneutralmoleculehavingan
atomwithalonepairofelectrons
Examples:
Nucleophile
Electrophile
a)H+andother+veions
b)Doubleandtriplebond
ofalkeneandalkynes
b)Halogenandhalogenacids
c)Compoundcontainingan
atomwithlonepair
c)H2SO4,HNO3,HNO2
d)R2O:,:NH3,R3N:,etc
d)NO2,AlCl3,BF2,etc
e)Lewisbase
e)Oxidisingagent(Cl2,Br2)
Molecules/atomswhichcontainunpairedelectronwhichare
neutralandreactive
FreeRadical
Example:H,CH3andCl
Resultofhomolyticcleavagein
acovalentbond
+ Na+ -OH
R-X
an alkyl halide
Ar-H
an aromatic
+ Br2
H2O
Fe
R-OH + Na+ X-
Ar-Br + HBr
Electrophilic
substitution
Additions
means
Areactioninwhichatomsorgroupsareaddedtothe
reactant.
H
C
+ Br2
H
Br Br
Bromine adds to the alkene (ethene).
Eliminations
means
Arxnthatinvolvestheremovalofatomsormoleculesfrom
thereactant
Br
H
C
H + KOH
H
+ K+ Br- + H2O
C
H
Rearrangements
H+
In the presence of acid, the alkene on the left rearranges to the alkene
on the right.
means
Areactioninwhichinvolvesthemigrationofanatomsor
groupsfromsitetoanotherwithinthesamemolecule
3)
4)
CH3CH3 + Cl2
uv
CH3 CH2 OH
Cl-
CH3CH2Cl + HCl
Cl
Cl 2
AlCl 3
CCl4
CH3CH(Br)CH2(Br)
H
5)
CH3 C = O + HCN
CH3 C - OH
CN
H
6)
CH3 CH2OH
7)
(CH3)2C = CH2 +
8)
CN- + CH3Br
9)
(CH3)2CHCl + NaOH
Br2
(CH3)2CBrCH2Br
CH3CN + Br-
(CH3)2CHOH + NaCl