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 ofphenolphthalein indicator and exactly 80 μL of 0.5M NaOH to the flask. Mix well. Add exactly 20 μL ofthe first alkyl halide to the flask and swirl. Measure and record the time required for the solution tobecome colorless. Repeat the procedure for the other seven alkyl halides. If any solution does notbecome colorless within 15 minutes, stop the reaction and record the time as >15 minutes. Alkyl halide1-chlorobutane1-bromobutanebromocyclopentanebromocyclohexane2-chlorobutane2-bromobutane2-chloro-2-methylpropane2-bromo-2-methylpropaneReaction Time2:09-2:247152:32-247 71512:34-2:49 >152:39-2:54 > 152:46 -3:01 7152:41-2:56 >152:47 3:02 >1512:43-2:46ReactivityunreactiveSlow/modAast

SN1 reactions proceed via formation of carbocation in a first order reaction in which the reactivity…

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

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter16: Aldehydes And Ketones

Section: Chapter Questions

Problem 16.63P

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Question

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.

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

Definition Definition Organic compounds in which one or more hydrogen atom in an alkane is replaced by a halogen atom (fluorine, chlorine, bromine, or iodine). These are also known as haloalkanes.

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