Solution Found!
In the mechanism for the acid-catalyzed hydrolysis of an
Chapter 16, Problem 25P(choose chapter or problem)
Problem 25P
In the mechanism for the acid-catalyzed hydrolysis of an ester,
a. what species could be represented by HB+?
b. what species could be represented by :B?
c. what species is HB+ most likely to be in the hydrolysis reaction?
d. what species is HB+ most likely to be in the reverse reaction?
Questions & Answers
QUESTION:
Problem 25P
In the mechanism for the acid-catalyzed hydrolysis of an ester,
a. what species could be represented by HB+?
b. what species could be represented by :B?
c. what species is HB+ most likely to be in the hydrolysis reaction?
d. what species is HB+ most likely to be in the reverse reaction?
ANSWER:Solution 25P
The mechanism of acid catalyzed hydrolysis of an ester involves the following steps:
In the first step, the lone pair of oxygen atom of the carbonyl group abstracts a proton from the acid medium.
The lone pair of electrons of the water molecule attacks at the electrophilic center of the carbonyl carbon forming a protonated tetrahedral intermediate I.
Step 3 of 8
The tetrahedral intermediate undergoes resonance and forms a non-protonated tetrahedral intermediate II.
Step 4 of 8
The non-protonated tetrahedral intermediate II is protonated with and reforms tetrahedral intermediate I.
Protonation of forms protonated tetrahedral intermediate III.
