H₂C OH OH H+ CH3 Esters can be synthesized by an acid-catalyzed nucleophilic acyl substitution between an alcohol and a carboxylic acid; this process is called the Fischer esterification reaction. Because the alcohol oxygen is a poor nucleophile, the carbonyl carbon is made a better electrophile by protonation of the carbonyl oxygen. The steps of the synthesis are all reversible. The reaction is generally driven to completion by using an excess of the liquid alcohol as a solvent, or by distilling off the product as it forms. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions 22 +X 0-4 :0: H₂O CH3 CH3 Hvo

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter17: Alcohols And Phenols
Section17.SE: Something Extra
Problem 71AP: A problem often encountered in the oxidation of primary alcohols to acids is that esters are...
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H3C
OH
OH
H+
CH3
Esters can be synthesized by an acid-catalyzed nucleophilic acyl substitution between an alcohol and a carboxylic acid; this process is called the Fischer
esterification reaction. Because the alcohol oxygen is a poor nucleophile, the carbonyl carbon is made a better electrophile by protonation of the
carbonyl oxygen. The steps of the synthesis are all reversible. The reaction is generally driven to completion by using an excess of the liquid alcohol as a
solvent, or by distilling off the product as it forms.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
CIX
10-4
H₂O
CH3
H₂O
CH3
Transcribed Image Text:H3C OH OH H+ CH3 Esters can be synthesized by an acid-catalyzed nucleophilic acyl substitution between an alcohol and a carboxylic acid; this process is called the Fischer esterification reaction. Because the alcohol oxygen is a poor nucleophile, the carbonyl carbon is made a better electrophile by protonation of the carbonyl oxygen. The steps of the synthesis are all reversible. The reaction is generally driven to completion by using an excess of the liquid alcohol as a solvent, or by distilling off the product as it forms. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CIX 10-4 H₂O CH3 H₂O CH3
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