(2-chloro-2-methylpropane) Preparation of t-butyl chloride

(CH 3 ) 3 COH + HCl (CH 3 ) 3 CCl + H 2 O Reaction Mechanism?

(CH 3 ) 3 COH + H-Cl (CH 3 ) 3 COH 2 + Cl + - Leaving Group

(CH 3 ) 3 C-OH 2 + (CH 3 ) 3 C + H2OH2O Cation

( CH 3 ) 3 C + + Cl - (CH 3 ) 3 CCl Cation Adds Chloride

+ sp 2 flat p tert-Butyl Cation

Reaction Coordinate

R.... OH Transition State

Animation

Substitution Nucleophilic 1 bond at a time SN1SN1

Increasing Stability

Side Reaction Main Reaction

SN1SN1 E1

Shake t-BuOH with concentrated HCl Separate layers Wash saturated aqueous NaCl Wash saturated aqueous NaHCO 3 Dry Distill Procedure

t-BuCl Shake t-BuOH with HCl

NaHCO 3 + HCl CO 2 + H 2 O + NaCl Wash to remove excess HCl

Cool receiver Distill product

Clamp joints

A + BC MW Use: 10 g A 20 g B Limiting Reagent Theoretical Yield Experimental Yield Yield Calculations

A + BC MW Cpd Mass MW Moles A 10 g B 20 g moles x 200 = 20 g Experimental yield (%): 100 x wt product / 20 Limiting Reagent Theoretical yield:

n-Butyl Alcohol + HBr

Transition State

Mechanism

Reaction Coordinate Energy Transition State

Substitution Nucleophilic 2 bonds at a time SN2SN2