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Effects of Leaving Group

Solvolysis of tert-Butyl Chloride and tert-Butyl Bromide - Effects of Leaving Group

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1 MB, 18 seconds

File: MOVIES/TRAM10/0293027.MOV

Voiceover
Two test tubes contain acetone and a basic solution of bromcresol green indicator. tert-butyl chloride is added to the first tube and tert-butyl bromide to the second. Color change of the indicator shows that the tertiary alkyl bromide reacts more rapidly than the tertiary chloride.

Discussion
To the aqueous acetone solutions used in the previous section are added tert-butyl chloride and tert-butyl bromide. The bromide reacts much more rapidly than the chloride. The reaction is an SN1 reaction and proceeds through the initial slow ionization of the alkyl halide. The bromide ion is a better leaving group than the chloride ion.


Design, Text and Demonstrator:  
  Gary Trammell University of Illinois at Springfield, Springfield, IL 62794
Videographer/Editor:  
  Steve Dykema University of Illinois at Springfield, Springfield, IL 62794
Voice:  
  Margaret Biddle University of Wisconsin - Madison, Madison, WI 53706
Audio Production:  
  Greg Minix University of Wisconsin - Madison, College of Engineering, Madison, WI 53706
  Jerrold J. Jacobsen University of Wisconsin - Madison, Madison, WI 53706