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| Reaction of Sodium Iodide with Bromobutane Isomers |
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Voiceover
Four test tubes contain a solution of sodium iodide in acetone. The following isomeric alkyl halides are added to separate tubes: 1-bromobutane, 1-bromo-2-methylpropane, 2-bromobutane, and 2-bromo-2-methylpropane. The solution containing the primary halide, 1-bromobutane, quickly becomes cloudy as sodium bromide precipitates. The more hindered primary halide, 1-bromo-2-methylpropane, reacts after about 5 minutes. The secondary halide, 2-bromobutane, reacts after about 13 minutes.
Discussion
This order of reactivity (primary > secondary halide) is characteristic of an SN2 reaction.
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Citation:
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Shriner, R. L.; Fuson, R. C.; Curtin, D. Y.; Morrill, T. C.
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The Systematic Identification of Organic Compounds; 6th ed.; Wiley: New York, 1980; pp 204-206.
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Design, Text and Demonstrator:
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Gary Trammell
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University of Illinois at Springfield, Springfield, IL 62794
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Videographer/Editor:
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Steve Dykema
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University of Illinois at Springfield, Springfield, IL 62794
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Voice:
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Margaret Biddle
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University of Wisconsin - Madison, Madison, WI 53706
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Audio Production:
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Greg Minix
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University of Wisconsin - Madison, College of Engineering, Madison, WI 53706
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Jerrold J. Jacobsen
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University of Wisconsin - Madison, Madison, WI 53706
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