|#ORGANIC REAcTION MecHANLSMS
Nucleophilic Sulastttukon Reachion.
Comparing the SN1 and the SN2 reactions
Syt S.2
Rate Law Unimolecular Bimolecular
(substrate and nucleophile)
(substrate only)
"Big Barrier Carbocation Steric hindrance
stab lity
Alkyl halide
(electrophile) 3>2>1 (worst) 1>2>>3° (worst)
Nucleophile Weak (generally Strong (generally
neutral) bearing a negative
charge)
Mech Solvent Polar protic
(e.g. alcohols)
Polar aprotic
(o.g DMSO, acatono)
mech.
Stereochemistry Mix of retention
and invorsion
Inversion only
S a
Ukmale cadar Nucieophalic Sulephiuk
keachan deeedo only on con
Tie ak
qi eaden le aleyf halida Bimolecaday Nudeo phitle Sub sttkuban ku
s order 4 keocho order A , maleculay:
tmole culaviky keoch'am
Ths reachD 4akes ploe do6 siees be cause he kak 4 neachon degdo ubon he cauc
CMs 4 both neachauis ie alkeyl halide and Nucieophile
Nudegle
- t X
SuosHtuton by hutrexy groub
’ROH + X*
danit
Sce-E makon4 nlmediate aeecaho Nudeophile lenvig Gro.
C
Halide io
tMechani
SM Atad< of nucleopnile on C may otaur
eiher hom t side or hom bacdside
"n s mchanismm, ne conkyurakon of alkayl
Rekahow
Tnvesiow
hati da ges nvertd. fr o calle d nver sian
of conipsaho ualden Brversian
Cire
Ce
Acid
Catalysed
Kydahon en 2 Reohel
0f AIkenes.
N.R
Nucleophilic Sulastttukon Reachion.
Comparing the SN1 and the SN2 reactions
Syt S.2
Rate Law Unimolecular Bimolecular
(substrate and nucleophile)
(substrate only)
"Big Barrier Carbocation Steric hindrance
stab lity
Alkyl halide
(electrophile) 3>2>1 (worst) 1>2>>3° (worst)
Nucleophile Weak (generally Strong (generally
neutral) bearing a negative
charge)
Mech Solvent Polar protic
(e.g. alcohols)
Polar aprotic
(o.g DMSO, acatono)
mech.
Stereochemistry Mix of retention
and invorsion
Inversion only
S a
Ukmale cadar Nucieophalic Sulephiuk
keachan deeedo only on con
Tie ak
qi eaden le aleyf halida Bimolecaday Nudeo phitle Sub sttkuban ku
s order 4 keocho order A , maleculay:
tmole culaviky keoch'am
Ths reachD 4akes ploe do6 siees be cause he kak 4 neachon degdo ubon he cauc
CMs 4 both neachauis ie alkeyl halide and Nucieophile
Nudegle
- t X
SuosHtuton by hutrexy groub
’ROH + X*
danit
Sce-E makon4 nlmediate aeecaho Nudeophile lenvig Gro.
C
Halide io
tMechani
SM Atad< of nucleopnile on C may otaur
eiher hom t side or hom bacdside
"n s mchanismm, ne conkyurakon of alkayl
Rekahow
Tnvesiow
hati da ges nvertd. fr o calle d nver sian
of conipsaho ualden Brversian
Cire
Ce
Acid
Catalysed
Kydahon en 2 Reohel
0f AIkenes.
N.R
