JCE Software Chemistry Comes Alive!
Secondary versus Tertiary Halides

Solvolysis of Alkyl Bromides: Secondary versus Tertiary Halides

View slide thumbnails.
View Slide Thumbnails
  Next movie.
View Next Movie
 

1 MB, 17 seconds

File: MOVIES/TRAM10/0291115.MOV

Voiceover
Two test tubes contain acetone and a basic solution of bromcresol green indicator. Isopropyl bromide is added to the first tube and tert-butyl bromide to the second. Production of hydrogen bromide causes the indicator to change color (from green to pink).

Discussion
Two test tubes contain acetone and aqueous sodium hydroxide (2.3 : 1 ratio) and bromcresol green indicator. Isopropyl bromide (2-bromopropane) is added to the first tube and tert-butyl bromide (2-bromo-2-methylpropane) to the second. The tertiary halide 2-bromo-2-methylpropane rapidly undergoes a SN1 reaction releasing hydrogen bromide and causing the indicator to change color from green to pink. The secondary halide 2-bromopropane reacts more slowly. This order of reactivity (tertiary > secondary halide) is characteristic for SN1 reactions in which a carbocation is formed.


       

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