Consider the reaction of a propanoate ester with hydroxide ion shown below. A series of four alcohol leaving groups were tested to determine which would be the best leaving group. Based on the pKa values of the alcohols, predict which alcohol would produce the fastest hydrolysis reaction. HO FOR A Alcohol I, pKa =16.0 B Alcohol II, pKa =10.0 C Alcohol III, pKa = 7.2 + ROH D Alcohol IV, pKa = 6.6

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
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section: Chapter Questions
Problem 20.27P
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Consider the reaction of a propanoate ester with hydroxide ion shown below. A
series of four alcohol leaving groups were tested to determine which would be the
best leaving group.
Based on the pKa values of the alcohols, predict which alcohol would produce the
fastest hydrolysis reaction.
HO
FOR
A
Alcohol I, pKa =16.0
B
Alcohol II, pKa =10.0
C
Alcohol III, pKa = 7.2
+ ROH
D
Alcohol IV, pKa = 6.6
Transcribed Image Text:Consider the reaction of a propanoate ester with hydroxide ion shown below. A series of four alcohol leaving groups were tested to determine which would be the best leaving group. Based on the pKa values of the alcohols, predict which alcohol would produce the fastest hydrolysis reaction. HO FOR A Alcohol I, pKa =16.0 B Alcohol II, pKa =10.0 C Alcohol III, pKa = 7.2 + ROH D Alcohol IV, pKa = 6.6
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