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

(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

tert-Butyl Cation + sp2 flat p

Transition State + + .... OH2 R

SN1 1 bond at a time Substitution Nucleophilic

Increasing Stability

Main Reaction Side Reaction

SN1 E1

Procedure Shake t-BuOH with concentrated HCl Separate layers Wash saturated aqueous NaCl Wash saturated aqueous NaHCO3 Dry Distill

Shake t-BuOH with HCl t-BuCl

Wash to remove excess HCl NaHCO3 + HCl CO2 + H2O + NaCl

Distill product Cool receiver

Clamp joints

Yield Calculations A + B C Limiting Reagent Theoretical Yield MW 100 100 200 Use: 10 g A 20 g B Limiting Reagent Theoretical Yield Experimental Yield

A + B C Cpd Mass MW Moles A 10 g 100 0.10 B 20 g 100 0.20 200 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

SN2 2 bonds at a time Substitution Nucleophilic