CHM 2211 Lecture Notes - Lecture 3: Dimethyl Sulfoxide, Protic Solvent, Racemization

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Substitution Nucieophitic Bimolecular
^Br
+0.0 CN
Na
.CN
=
Af
7=~ +Br
-
acetone
inversion
Of
configuration
Rate .
tk[
aiinyi halide ][ nuc ]=K[£][NaCNT±
Substitution Nucleophilic uni molecular
TBR
)'t ¥4€ on
Hid :v-0 odHZG :
q
µ
#
o~+Br→1~
- ' o¥r
Ckeep eye ~
out for rearrangements )racemit
nuc +HZOQ
So%ent
(sowolusus )
SN '
Rate =k[ alkyl halide ]= in [¥]
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Nac Strong weak
(negative sone )is 01h
alkyl
CHZ >>20 30 >
halide slow
or resonance
Solvent Polar Aprotic polar Protic
(preferred )(Hbonding )
L.6I>Br >Cl I>Br >Cl
Stereo Inversion Racemization
larA#tC (cant do SNI )
DMSO acetone
DMF acetonitriie
o:O :
:O
:
''
11 11
/s -nany--CIN
posarprotic
:O
:
'+20 R-OH jy [Agnos ]
R
OH Parcipitate out
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nuc
+00
Nt #~~3 SNZ
DMSO
esectrophile solvent
.primary cant SNI
)-¥4 ,SN ]
Bnz
Aµ@
Br
yrearrange *
go.ca ,
#It's )E
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