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

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

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

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

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

6. + sp 2 flat p tert-Butyl Cation

7. Reaction Coordinate

8. R.... OH 2 + + Transition State

9. Animation

10. Substitution Nucleophilic 1 bond at a time SN1SN1

11. Increasing Stability

12. Side Reaction Main Reaction

13. SN1SN1 E1

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

15. t-BuCl Shake t-BuOH with HCl

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

17. Cool receiver Distill product

18. Clamp joints

19. A + BC MW 100 100200 Use: 10 g A 20 g B Limiting Reagent Theoretical Yield Experimental Yield Yield Calculations

20. A + BC MW 100 100200 Cpd Mass MW Moles A 10 g 100 0.10 B 20 g 100 0.20 0.10 moles x 200 = 20 g Experimental yield (%): 100 x wt product / 20 Limiting Reagent Theoretical yield:

21. n-Butyl Alcohol + HBr

22. Transition State

23. Mechanism

24. Reaction Coordinate Energy Transition State

25. Substitution Nucleophilic 2 bonds at a time SN2SN2