Draw the products of the following hydrolysis.
Draw the products of the following hydrolysis. 
Draw the products of the following hydrolysis.
General guidance
Concepts and reason
Hydrolysis:
It is the chemical reaction between a water molecule and another compound, in which the water molecule ionizes and splits the other compound forming two or more products.
Fundamentals
Hydro means water and lysis means unbind. The reaction involves the cleavage of chemical bonds using water. Hydrolysis of an ester gives both an acid and an alcohol as products.
The mechanism of the hydrolysis of an ester in the presence of an acid or proton source is as follows:
1.The double bonded oxygen of an ester abstracts a proton and forms a hydroxonium ion.
2.The attack of the water molecule on an electrophilic carbon.
3.A proton transfer followed by the cleaving of the alcohol group, forming a carbocation.
4.Deprotonation to yield the final product.
Step-by-step
Step 1 of 3
The double bonded oxygen of the ester abstracts the proton and forms a hydroxonium ion, making the adjacent carbon atom more electrophilic in nature. The oxygen from the water molecule attacks the electrophilic carbon and forms a hydronium ion.
The more electron-rich oxygen atom will abstract the proton. The more electron-rich oxygen atom is the oxygen atom which is double bonded with carbon, as it has two lone pairs of electrons as well as a double bond with the carbon atom. Hence, take care to correctly show the proton abstraction.
Correct scheme:
Incorrect scheme:
Perform a proton transfer followed by the cleaving of the alcohol group.
Step 2 of 3
The oxygen attached to the alkyl group abstracts the proton from the hydronium ion and bears a positive charge on it. The carbon-oxygen bond with a positive charge cleaves, forming an ethanol and a carbocation.
Deprotonate the hydrogen atom in order to yield the respective acids.
Step 3 of 3
The proton of the hydroxyl group from the molecule that has carbocation (carbon with positive charge) deprotonates to form a neutralized stable product called acetic acid.
Answer
Answer only
н н* R—С—О—R R—с. -о—R
н Н R—С—О—R R—с -о—R Н Н т
Proton transfer: H Н Proton transfer R C R C -R -R Н н Н Departure of alcohol: н н R —с -R R CO НО—R Alcohol Н Н : O I :O I . I
н -н* R C Ht C OH R Caroboxylic acid H
-н Н2 н* Н2 “CHз Нас “CНз Hас Н :O —н Н2 С. “CHз Hас H н O т O: O:
-н О: Н2 Ht На с. “CHз Hзс “CHз Hас :O: O
о о. Н2 с н* Н2 с. “CНз “CHз Нас Нас Н :O:
:O -н —Н О Н2 с. На с “CHз “CHз Нас Hас Н Н : O -н Н2 с. Со “CHз Нас н O -т O с
-н -н* С HзС H* Hас : ОН Н
(он)
Н2 Н2 Н* CH3 НО Hас н Hас Н “CHз ОН о—о
Н2 Н2 Н* CH3 НО Hас н Hас Н “CHз ОН о—о
