List the alkyl halides in order of decreasing reactivity towards the Sn1 reaction

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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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List the alkyl halides in order of decreasing reactivity towards the Sn1 reaction

SN1 Reaction Conditions:
Add 10 mL of a 50% 2-propanol/water solution to a 25 m L Erlenmeyer flask. Add 2 drops of
phenolphthalein indicator and exactly 80 μL of 0.5M NaOH to the flask. Mix well. Add exactly 20 μL of
the first alkyl halide to the flask and swirl. Measure and record the time required for the solution to
become colorless. Repeat the procedure for the other seven alkyl halides. If any solution does not
become colorless within 15 minutes, stop the reaction and record the time as >15 minutes.
Transcribed Image Text:SN1 Reaction Conditions: Add 10 mL of a 50% 2-propanol/water solution to a 25 m L Erlenmeyer flask. Add 2 drops of phenolphthalein indicator and exactly 80 μL of 0.5M NaOH to the flask. Mix well. Add exactly 20 μL of the first alkyl halide to the flask and swirl. Measure and record the time required for the solution to become colorless. Repeat the procedure for the other seven alkyl halides. If any solution does not become colorless within 15 minutes, stop the reaction and record the time as >15 minutes.
Alkyl halide
1-chlorobutane
1-bromobutane
bromocyclopentane
bromocyclohexane
2-chlorobutane
2-bromobutane
2-chloro-2-methylpropane
2-bromo-2-methylpropane
Reaction Time
2:09-2:24
715
2:32-247 715
12:34-2:49 >15
2:39-2:54 > 15
2:46 -3:01 715
2:41-2:56 >15
2:47 3:02 >15
12:43-2:46
Reactivity
unreactive
Slow/mod
Aast
Transcribed Image Text:Alkyl halide 1-chlorobutane 1-bromobutane bromocyclopentane bromocyclohexane 2-chlorobutane 2-bromobutane 2-chloro-2-methylpropane 2-bromo-2-methylpropane Reaction Time 2:09-2:24 715 2:32-247 715 12:34-2:49 >15 2:39-2:54 > 15 2:46 -3:01 715 2:41-2:56 >15 2:47 3:02 >15 12:43-2:46 Reactivity unreactive Slow/mod Aast
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