Preparation of Esters
Chapter 21. Carboxylic Acid Derivatives: Esters and
AmidesDisusun oleh :
Khoirul Haniin125090207111010Fitriana Dewi
Kurniawati125090207111011Mila Fatuzzahroh125090207111023Ryzki
Martha Anjani105090201111010
Based on McMurrys Organic Chemistry, 7th editionPreparation of
Esters[1]Esters are usually prepared from carboxylic acids2
Ester from carboxylic acid with alkyl halide [2]3
Acid catalysist esterification : carboxylic acid with alcohol
[3]
4Conversion of An Acyl Chloride Into An Ester [2]
Asam asetatAsetil Klorida5
Conversion of An Acyl Chloride Into An Ester [2]Metil
AsetatAsetil Klorida6Reactions of Esters [1]Less reactive toward
nucleophiles than are acid chlorides or anhydrides
Cyclic esters are called lactones and react similarly to acyclic
esters 78Hydrolysis: Conversion of Esters into Carboxylic Acids
[1]An ester is hydrolyzed by aqueous base or aqueous acid to yield
a carboxylic acid plus an alcohol
8Mechanism of Ester Hydrolysis [1]Hydroxide catalysis via an
addition intermediate
9
Conversion of metyl acetate into acetic acid [3]Metil AsetatAsam
asetat1011Aminolysis of Esters [1]Ammonia reacts with esters to
form amides
11Mechanism of Ester Aminolysis [2]
12
Mechanism of Reaction 1314Reduction: Conversion of Esters into
Alcohols [1]Reaction with LiAlH4 yields primary alcohols
14Mechanism of Reaction 115
Mechanism of Reaction 2
16Mechanism of Reduction of Esters [1]Hydride ion adds to the
carbonyl group, followed by elimination of alkoxide ion to yield an
aldehydeReduction of the aldehyde gives the primary alcohol
17
Conversion of methyl propionate into propanol [3]1819Reaction of
Esters with Grignard Reagents [1]React with 2 equivalents of a
Grignard reagent to yield a tertiary alcohol
19Mechanism of Reaction
20Conversion of an ester into a tertiary alcohol [3]
2121.7 Chemistry of Amides [1]Amides are abundant in all living
organismsproteins, nucleic acids, and other pharmaceuticals have
amid functional groups
22Preparation of Amides [1]Prepared by reaction of an acid
chloride with ammonia, monosubstituted amines, or disubstituted
amines
23Mechanism Reaction 1[2]
24Mechanism Reaction 2[2]
25Mechanism Reaction 3[2]
26Reactions of Amides [1]Heating in either aqueous acid or
aqueous base produces a carboxylic acid and amineAcidic hydrolysis
by nucleophilic addition of water to the protonated amide, followed
by loss of ammonia
2728Basic Hydrolysis of Amides [1]Addition of hydroxide and loss
of amide ion
28Mechanism for acid-catalyzed hydrolysis of an amide [3]29
Reduction: Conversion of Amides into Amines [1]Reduced by LiAlH4
to an amine rather than an alcoholConverts C=O CH2
30 Mechanism of Reduction [1]Addition of hydride to carbonyl
groupLoss of the oxygen as an aluminate anion to give an iminium
ion intermediate which is reduced to the amine
31
Conversion of amide into amine [3]32Mechanism for the reaction
of an N-subtituted amide with hydride ion [3]33
34Conversion of amide into amine [3]Reference[1] McMurry, J.,
2008, Organic Chemistry, Seventh Edition, Thomson Learning, Inc.,
USA[2] Hart, H., Leslie E.C., David J.H., 2003,Kimia Organik :
Suatu Kuliah Singkat, Edisi Kesebelas, diterjemahkan oleh : Suminar
S.A., Penerbit Erlangga, Jakarta[3]Bruice, P.Y., 2004, Organic
Chemistry, Fourth Edition, Pearson Prentice Hall, New Jersey35