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Solvolysis of Bromobutane Isomers

Isomers of C4H9Br are added to an alkaline aqueous acetone solution containing bromcresol green indicator.

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2.6 MB, 54 seconds

File: MOVIES/TRAM10/0304918.MOV

Voiceover
Isomers of bromobutane are added to an alkaline aqueous acetone solution containing bromcresol green indicator. The solvolysis is revealed by the indicator changing from green to red as hydrogen bromide is liberated in the reaction. The tertiary halide 2-bromo-2-methylpropane reacts fastest. The secondary halide 2-bromobutane reacts next followed by the more hindered primary halide 1-bromo-2-methylpropane. The primary 1-bromobutane does not react under these conditions. The order of reactivity is characteristic of an SN1 reaction mechanism.

Discussion
Isomers of C4H9Br were added to an alkaline aqueous acetone solution containing bromcresol green indicator. The solvolysis is revealed by the indicator changing from green to red as hydrogen bromide is liberated in the reaction. The tertiary halide 2-bromo-2-methylpropane reacts fastest. The secondary halide 2-bromobutane reacts next followed by the more hindered primary halide 1-bromo-2-methylpropane. The primary 1-bromobutane does not react under these conditions. The order of reactivity of tertiary > secondary > primary halides indicates an SN1 mechanism in which a free carbocation is formed as described in section 10a.


       

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