1 / 25

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.

brant
Download Presentation

Preparation of t-butyl chloride

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  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

More Related