Preparation of t butyl chloride
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Preparation of t-butyl chloride. (2-chloro-2-methylpropane). (CH 3 ) 3 C OH + H Cl. Reaction Mechanism?. (CH 3 ) 3 C Cl + H 2 O. Leaving Group. (CH 3 ) 3 C OH + H - Cl. +. -. (CH 3 ) 3 C OH 2 + Cl. Cation. +. (CH 3 ) 3 C -OH 2. +. (CH 3 ) 3 C. H 2 O. Mechanism.

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Preparation of t butyl chloride
Preparation of t-butyl chloride

(2-chloro-2-methylpropane)


Reaction mechanism

(CH3)3COH + HCl

Reaction Mechanism?

(CH3)3CCl + H2O


Leaving group
Leaving Group

(CH3)3COH + H-Cl

+

-

(CH3)3COH2 + Cl


Cation
Cation

+

(CH3)3C-OH2

+

(CH3)3C

H2O


Mechanism
Mechanism

-

+

(CH3)3C

+ Cl

(CH3)3CCl


Tert butyl cation
tert-Butyl Cation

+

sp2 flat

p



Transition state
Transition State

+

+

....

OH2

R



S n 1
SN1

1 bond at a time

Substitution

Nucleophilic



Main reaction
Main Reaction

Side Reaction


E1 sn1
E1 SN1

SN1

E1


Procedure
Procedure

Shake t-BuOH with concentrated HCl

Separate layers

Wash saturated aqueous NaCl

Wash saturated aqueous NaHCO3

Dry

Distill



Wash to remove excess hcl
Wash to remove excess HCl

NaHCO3 + HCl

CO2 + H2O + NaCl


Distill product
Distill product

Cool receiver



Yield calculations
Yield Calculations

A + B

C

MW 100

100

200

Use: 10 g A 20 g B

Limiting Reagent

Theoretical Yield

Experimental Yield


A + B

C

MW 100

100

200

Cpd Mass MW Moles

Limiting

Reagent

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




Transition state1
TransitionState

Energy

Reaction Coordinate


S n 2
SN2

2 bonds at a time

Substitution

Nucleophilic


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