Preparation of t-butyl chloride

(2-chloro-2-methylpropane)

C

CH3

CH3

CH3

OHHCl

C

CH3

CH3

CH3

Cl + H2O

t-butyl alcohol t-butyl chloride

Preparation of t-butyl chloride

(CH3)3COH + HCl

(CH3)3CCl + H2O

Reaction Mechanism?

(CH3)3COH + H-Cl

(CH3)3COH2 + Cl + -

Leaving Group

(CH3)3C-OH2 +

(CH3)3C + H2O

Cation

(CH3)3C +

+ Cl-

(CH3)3CCl

Mechanism

+sp2 flat

p

tert-Butyl Cation

Reaction Coordinate

R .... OH2

+ +

Transition State

Animation

Substitution

Nucleophilic

1 bond at a time

SN1

Increasing Stability

Side Reaction

C

CH3

CH3

CH3

OHHCl

C

CH3

CH3

CH3

Cl + H2O

t-butyl alcohol t-butyl chloride

C

CH3

CH3

CH3

OHHCl

+ H2O

t-butyl alcohol

CH2C

CH3

CH3

isobutylene

Main Reaction

CH2C

CH3

CH3

C

CH3

CH3CH3

C

CH3

CH3

CH3

Cl

E1 SN1

E1 SN1

Shake t-BuOH with concentrated HCl

Separate layers

Wash saturated aqueous NaCl

Wash saturated aqueous NaHCO3

Dry

Distill

Procedure

t-BuCl

Shake t-BuOH with HCl

NaHCO3 + HCl

CO2 + H2O + NaCl

Wash to remove excess HCl

Cool receiver

Distill product

Clamp joints

A + B CMW 100 100 200

Use: 10 g A 20 g B

Limiting Reagent

Theoretical Yield

Experimental Yield

Yield Calculations

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

CH3CH2CH2CH2OH

n-butyl alcohol

HBr

CH3CH2CH2CH2Br

n-butyl bromide

n-BuOH n-BuBr

RCH2OH + H+ RCH2OH2

+

C

R

HH

OH2Br

transition state

RCH2Br

Animation

XCY

- -

CY X-XCY

-

Reaction Coordinate

Energy

TransitionState

Substitution

Nucleophilic

2 bonds at a time

SN2