Chapter 21 - Esters

Fischer Esterification

Carboxylic acid +

R-OH/H+

Nucleophilic Acyl Substitution Synthesis of Esters

Acid chloride +

alcohol

Ester synthesis:

Anhydride +

alcohol

Transesterification:

Ester +

alcohol

Diazomethane Synthesis of Ester:

Acid +

CH2N2

Sn2 Mechanism:
Acid +

1) NaOH

2) R-X

Nonenclature:

“-e” —>

“-oate”

Cyclic ester nomenclature

add “lactone” to acid name

Ester hydrolysis

Ester + ____ —> Alcohol

H2O, H+ or H3O+

Ester hydrolysis

Ester —>

Alcohol

Ester Reduction to Alcohol

Ester + ?

1) LiAlH4

2) H2O

Saponification

Ester + _____ —> alcohol

1) OH-

2) H3O+

Saponification

Ester —> ?

Alcohol

Aminolysis

Ester + ? —> amide

NHRn

Aminolysis

Ester —> ?

Amide

Reduction of Ester to Aldehyde

Ester + ? —> aldehyde

1) DIABH

2) H2O

Reaction of Esters with Grignards

Ester + ? —> alcohol

1) MgBr

2) H2O

Requirements for Ammonolysis

1. Nucleophile must be NH3 or primary amine

2. prolonged heating