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Preparation of t-butyl chloride

Preparation of t-butyl chloride. (2-chloro-2-methylpropane). (CH 3 ) 3 C OH + H Cl. Reaction Mechanism?. (CH 3 ) 3 C Cl + H 2 O. Leaving Group. (CH 3 ) 3 C OH + H - Cl. +. -. (CH 3 ) 3 C OH 2 + Cl. Cation. +. (CH 3 ) 3 C -OH 2. +. (CH 3 ) 3 C. H 2 O.

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Preparation of t-butyl chloride

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  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. Cation Adds Chloride - + (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

  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 Theoretical yield: MW 100 100 200 Cpd Mass MW Moles Limiting Reagent 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

  21. n-Butyl Alcohol + HBr

  22. Transition State

  23. Mechanism

  24. TransitionState Energy Reaction Coordinate

  25. SN2 2 bonds at a time Substitution Nucleophilic

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