Preparation of t-butyl chloride - University of Illinois...
Transcript of Preparation of t-butyl chloride - University of Illinois...
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Preparation of t-butyl chloride(2-chloro-2-methylpropane)
CCH3
CH3CH3
OHHCl
CCH3
CH3CH3
Cl + H2O
t-butyl alcohol t-butyl chloride
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(CH3)3COH + HCl
(CH3)3CCl + H2O
Reaction Mechanism?
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(CH3)3COH + H-Cl
(CH3)3COH2 + Cl + -
Leaving Group
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(CH3)3C-OH2 +
(CH3)3C + H2O
Cation
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(CH3)3C + + Cl-
(CH3)3CCl
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C CH3
CH3
CH3
tert-Butyl Cation
+sp2 flat
p
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2
Transition State
δ δ
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Substitution
Nucleophilic
1 bondat a time
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Increasing Stability
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Main Reaction
Side Reaction
CCH3
CH3CH3
OHHCl
CCH3
CH3CH3
Cl + H2O
t-butyl alcohol t-butyl chloride
CCH3
CH3CH3
OHHCl
+ H2O
t-butyl alcohol
CH2CCH3
CH3
isobutylene
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CH2CCH3
CH3
C
CH3
CH3CH3
CCH3
CH3CH3
Cl
E1 N
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ProcedureShake t-BuOH with concentrated HCl
Separate layers
Wash saturated aqueous NaCl
Wash saturated aqueous NaHCO3
Dry
Distill
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t-BuCl
Shake t-BuOH with HCl
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NaHCO3 + HCl
CO2 + H2O + NaCl
Wash to remove excess HCl
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Distill product
Cool receiver
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Clamp joints
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Yield Calculations
A + B CMW 100 100 200
Use: 10 g A 20 g B
Limiting Reagent
Theoretical Yield
Experimental Yield
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A + B CMW 100 100 200
Cpd Mass MW Moles
A 10 g 100 0.10
B 20 g 100 0.20
Theoretical yield:0.10 moles x 200 = 20 g
Experimental yield (%):100 x wt product / 20
LimitingReagent
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CH3CH2CH2CH2OH n-butyl alcohol
HBr
CH3CH2CH2CH2Brn-butyl bromide
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RCH2OH + H+ RCH2OH2+
C
R
HHOH2Br
δ− δ+
transition state
RCH2Br
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Substitution
Nucleophilic
2 bonds ata time