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

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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


Reaction coordinate

Reaction Coordinate


Transition state

Transition State

+

+

....

OH2

R


Animation

Animation


S n 1

SN1

1 bond at a time

Substitution

Nucleophilic


Increasing stability

Increasing Stability


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


Shake t buoh with hcl

Shake t-BuOH with HCl

t-BuCl


Wash to remove excess hcl

Wash to remove excess HCl

NaHCO3 + HCl

CO2 + H2O + NaCl


Distill product

Distill product

Cool receiver


Clamp joints

Clamp joints


Yield calculations

Yield Calculations

A + B

C

MW 100

100

200

Use: 10 g A 20 g B

Limiting Reagent

Theoretical Yield

Experimental Yield


Preparation of t butyl chloride

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


N buoh n bubr

n-BuOH n-BuBr


Animation1

Animation


Transition state1

TransitionState

Energy

Reaction Coordinate


S n 2

SN2

2 bonds at a time

Substitution

Nucleophilic


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