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

2. (CH3)3COH + HCl
(CH3)3CCl + H2O
Reaction Mechanism?

3. (CH3)3COH + H-Cl + -
(CH3)3COH Cl
Leaving Group

4. +
(CH3)3C-OH2 +
(CH3)3C
H2O
Cation

5. - +
(CH3)3C
+ Cl
(CH3)3CCl

6. tert-Butyl Cation +
sp2 flat p

8. Transition State + +
....
OH2 R

10. SN1
1 bond at a time
Substitution
Nucleophilic

11. Increasing Stability

12. Main Reaction
Side Reaction

13. SN1 E1

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

15. Shake t-BuOH with HCl
t-BuCl

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

17. Distill product
Cool receiver

18. Clamp joints

19. 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

20. 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 g
B g
Theoretical yield:
0.10 moles x 200 = 20 g
Experimental yield (%):
100 x wt product / 20

24. SN2
2 bonds at a time
Substitution
Nucleophilic