1. Acid-catalized rearrangement reactions of simple alcohols are quite common. Based on the mechanism shown in the background, can you predict the product and mechanisms for the reation of a strong acid and isopropyl alcohol? Answer: OH H* - H20 - H* CH3 CH CH CH3 CH CH CH3 CH, CH H2C C CH3 H. 2. Why is acetic acid a better acid catalyst than hydrogen chloride for this carbocation rearrangement?

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
Chapter10: Alcohols
Section: Chapter Questions
Problem 10.50P
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1. Acid-catalized rearrangement reactions of simple alcohols are quite common. Based
on the mechanism shown in the background, can you predict the product and
mechanisms for the reation of a strong acid and isopropyl alcohol?
Answer:
OH
OH2
H*
H20
H+
CH3
CH
CH
CH.
CH
CH3
CH3
CH3
CH3
CH3
H2C=C
H.
2. Why is acetic acid a better acid catalyst than hydrogen chloride for this carbocation
rearrangement?
Transcribed Image Text:ns 1. Acid-catalized rearrangement reactions of simple alcohols are quite common. Based on the mechanism shown in the background, can you predict the product and mechanisms for the reation of a strong acid and isopropyl alcohol? Answer: OH OH2 H* H20 H+ CH3 CH CH CH. CH CH3 CH3 CH3 CH3 CH3 H2C=C H. 2. Why is acetic acid a better acid catalyst than hydrogen chloride for this carbocation rearrangement?
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Acetic acid is a better acid catalyst than HCL because in HCL, Cl- ion behave as strong nucleophile and the nucleophile attack on the the substrate and nucleophilic substitution reaction take place as well as acid catalysed reaction 

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