Preparation of t-butyl chloride

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

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

3. Leaving Group (CH3)3COH + H-Cl + - (CH3)3COH2 + Cl

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

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

6. tert-Butyl Cation + sp2 flat p

7. Reaction Coordinate

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

9. Animation

10. SN1 1 bond at a time Substitution Nucleophilic

11. Increasing Stability

12. Main Reaction Side Reaction

13. E1 SN1 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 MW 100 100 200 Use: 10 g A 20 g B Limiting Reagent Theoretical Yield Experimental Yield

20. 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

21. n-BuOH n-BuBr

23. Animation

24. TransitionState Energy Reaction Coordinate

25. SN2 2 bonds at a time Substitution Nucleophilic