2-Pentanol reacts with hydrochloric acid to undergo a substitution reaction. What is the mechanism for this, showing all the possible products. However, if 2- butanol reacts with p-toluene sulfonic acid (p-TSA) only the elimination product is formed. No substitution product is observed. Why? Identify the possible products for this reaction.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
Section19.SE: Something Extra
Problem 36MP: It is not uncommon for organic chemists to prepare acetals by an exchange-type process known as...
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2-Pentanol reacts with hydrochloric acid to undergo a substitution reaction. What
is the mechanism for this, showing all the possible products. However, if 2-
butanol reacts with p-toluene sulfonic acid (p-TSA) only the elimination product is
formed. No substitution product is observed. Why? Identify the possible products
for this reaction.
Transcribed Image Text:2-Pentanol reacts with hydrochloric acid to undergo a substitution reaction. What is the mechanism for this, showing all the possible products. However, if 2- butanol reacts with p-toluene sulfonic acid (p-TSA) only the elimination product is formed. No substitution product is observed. Why? Identify the possible products for this reaction.
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