ANDELECTROPHILE
IUCLEOPHILE REACTIONMECHANISMS
thatusuallyhasalotoflonepairsorhasanegative
NUCLEOPHILEspecies chargelove ELECTRONPUSHINGdepicttheflowormovementofelectronsduringreactions
clewisbase
the
nucleusseeks
p ositive
change ADDITIONS
EX H2OOHNits Definitioncarboncarbon bond
d ouble w here bonds broken
are a ndinitsplace.obondsfrmt.tw
bearpositivecharge
and outelectronsand
seek seeks charge
negative newatomsorgroupsofatm
I Iffy
É'dt'tFestCHIBusFears Alll NEEDtoknow
FACTIONSBETWEENNUCLEOPHILESANDELECTROPHILES
1 dex
EX
H CH H E CH Hydration
44 4,0 d
É JH
BITE F IE
1 gd
Br x
am
jpg p
acidicconditionsbehaves
electrophileUnder more
Hydrogenation
Y ft Hz dd
Hit
REACTIONCOORDINATEDIAGRAMS transition
stage 2
to H
gyp y jp
Nucleo Electro
ARBOCATION le É heatutreaction
withapositive
EFINITIONcarbon charge
as
my
Ijjjjjjj
CH
y
1
y stable
more than
reactionintermediates
TRANSITIONSTATESlifetimes
ELECTROPHILICADDITIONS
onlyontheorder
elimeslongerthanittateserthebondtubate
ofthelifetimeofabondvibration
Definitionoverallreactionofelectrophilicspeciesaddingto
CH
Tertiary
CH
Secondary
I H H methyl
KEYSTEPinvolves
bonds
Primary methyl electronsofthealkenereactingasanucleophileorBronsted
Lowry
TABILITY CHARACTERISTICFEATURESMAKING MOLECULE
A ORANIONELECTROPHILIC
1 Effect
Inductive
1 reflected
Regionoflowelectrondensity positive
byapartialorfll charge
of
2Hyperconjugation relatedtotheoverlap atomicorbitals Aidsinanelectonrichregionofanucleophile attraction
electrostatic
through
orbital
2 Lackofanoctetonanatom
Iffyptyp 3 Relativelyweakbondtoanatomthatcandepartasastableionormolecule
HClHB andHI
jiff
1A ye yep theoctet
andoxygenobeys
REGIOSELECTIVEREACTIONreactioninwhich
onedirectionofbondformingorbrea
ingoccursinpreferencetallotherdirectionsofbo
formingorbreaking
asMARKOVNIKOV'sRULEadditionofH X
Generalizationknown
worse
4 I 12 moststable
notstabilizeBycan
Anything
only 3 structures
n
n
drawcandrawsresonance wecanputthepositi
EFFECT
INDUCTIVE
of
number hydrogens
DEFINITIONelectron
deficiency ofthecationiccarboneventsexertsonelectronwithdrawing
thatpolarizeselectronsfromadjacentsigma towardit
bonds
IUCLEOPHILE REACTIONMECHANISMS
thatusuallyhasalotoflonepairsorhasanegative
NUCLEOPHILEspecies chargelove ELECTRONPUSHINGdepicttheflowormovementofelectronsduringreactions
clewisbase
the
nucleusseeks
p ositive
change ADDITIONS
EX H2OOHNits Definitioncarboncarbon bond
d ouble w here bonds broken
are a ndinitsplace.obondsfrmt.tw
bearpositivecharge
and outelectronsand
seek seeks charge
negative newatomsorgroupsofatm
I Iffy
É'dt'tFestCHIBusFears Alll NEEDtoknow
FACTIONSBETWEENNUCLEOPHILESANDELECTROPHILES
1 dex
EX
H CH H E CH Hydration
44 4,0 d
É JH
BITE F IE
1 gd
Br x
am
jpg p
acidicconditionsbehaves
electrophileUnder more
Hydrogenation
Y ft Hz dd
Hit
REACTIONCOORDINATEDIAGRAMS transition
stage 2
to H
gyp y jp
Nucleo Electro
ARBOCATION le É heatutreaction
withapositive
EFINITIONcarbon charge
as
my
Ijjjjjjj
CH
y
1
y stable
more than
reactionintermediates
TRANSITIONSTATESlifetimes
ELECTROPHILICADDITIONS
onlyontheorder
elimeslongerthanittateserthebondtubate
ofthelifetimeofabondvibration
Definitionoverallreactionofelectrophilicspeciesaddingto
CH
Tertiary
CH
Secondary
I H H methyl
KEYSTEPinvolves
bonds
Primary methyl electronsofthealkenereactingasanucleophileorBronsted
Lowry
TABILITY CHARACTERISTICFEATURESMAKING MOLECULE
A ORANIONELECTROPHILIC
1 Effect
Inductive
1 reflected
Regionoflowelectrondensity positive
byapartialorfll charge
of
2Hyperconjugation relatedtotheoverlap atomicorbitals Aidsinanelectonrichregionofanucleophile attraction
electrostatic
through
orbital
2 Lackofanoctetonanatom
Iffyptyp 3 Relativelyweakbondtoanatomthatcandepartasastableionormolecule
HClHB andHI
jiff
1A ye yep theoctet
andoxygenobeys
REGIOSELECTIVEREACTIONreactioninwhich
onedirectionofbondformingorbrea
ingoccursinpreferencetallotherdirectionsofbo
formingorbreaking
asMARKOVNIKOV'sRULEadditionofH X
Generalizationknown
worse
4 I 12 moststable
notstabilizeBycan
Anything
only 3 structures
n
n
drawcandrawsresonance wecanputthepositi
EFFECT
INDUCTIVE
of
number hydrogens
DEFINITIONelectron
deficiency ofthecationiccarboneventsexertsonelectronwithdrawing
thatpolarizeselectronsfromadjacentsigma towardit
bonds
