Turunan Asam Karboksilat

Klorida asam
Asam anhidrida
Ester
Amida
Nitril

Substitusi Nukleofilik
Sifat Fisik Senyawa Turunan
Asam Karboksilat
Reaktivitas Turunan Asam
Karboksilat
Reaksi Konversi Gugus Fungsu Turunan Asam Karboksilat
Substitusi Nukleofilik
Tatanama IUPAC
(menggunakan template asam karboksilat)
O O O

Cl O
drop "ic acid" add "yl chloride" drop "acid" add "anhydride"
pentanoyl chloride pentanoic anhydride
O O

OCH3 NH2
"alkyl" _ drop "ic acid" add "ate" drop "oic acid" add "amide"
methyl pentanoate pentanamide
CN
drop "ic acid" add "e_nitrile"
pentanenitrile
 Klorida Asam
OCH3 O
CCl Cl

o-methoxybenzoyl chloride (E) 2-octenoyl chloride

O
CH3O CH2CCl

(p-methoxyphenyl)acetyl chloride
Asam Anhidrida
O O
O O C C
O CH3
O
butanoic anhydride acetic benzoic anhydride
butyric anhydride

O
OH O O O
HO
O
succinnic acid succinnic anhydride
Ester
O
COCH2CH2CH3 O

O
propyl benzoate (Z) cyclopentyl 2-butenoate
O O
COCH2CH(CH3)2 CH2COCH2CH3

isobutyl cyclohexanecarboxylate ethyl phenylacetate

Amida
O
CNH2

CH3 H2N O
meta methylbenzamide 2-ethyl-3-methylpentanamide
-ethyl--methylvaleramide
O
CN(CH3)2 O

HCN
H
N-benzylformamide
N,N-dimethylcyclopentanecarboxamide
Lacton (ester siklik) O
O
O
HO OH + H2O

-hydroxyvaleric acid -valerolactone

O
O
O
OH + H2O

OH
-hydroxyenanthic acid -enantholactone
 Asam γ-Hidroksibutirat

HO CO 2H HO CO2 Na

-hydroxybutyric acid sodium 4-hydroxybutanoate

or sodium -hydroxybutyrate
H 3O
+ (GHB)

CNS depressant
O as of 2000, Schedule I
controlled substance
O + H2O
If mixed with ROH, the depressant
effects are enhanced
-butyrolactone
Semua turunan asam karboksilat
dapat dihidrolisis menghasilkan asam
karboksilat O O

(CH3)2CHO OCH(CH3)2
diisopropyl pimelate
Hydrolysis
+
H3O or
in base
O O

HO OH
+ 2 (CH3)2CHOH
 Tuliskan tiga produk dari hidrolisis
senyawa berikut?
O
C N(CH2CH3)2
+
O H3O

O products are carboxylic acid(s)

+ conjugate acid of the LGs
Two hydrolyzable groups
Produk Hidrolisis
O
C N(CH2CH3)2 CO2H
+ OH
O H3O

+ HN(CH2CH3)2
O
HO
+
O
Hidrolisis of klorida asam
Pembuatan klorida asam
O O
COH CCl
SOCl2
+ SO2
in N
+ HCl
 O O

SOCl2, pyridine CCl

OH
+ HCl
+ SO2
O
S
Cl Cl O
O S
O Cl
C OH
C O
Cl

O O
O
S S
S Cl O Cl
O Cl
O Cl
C OH C
C OH pyr: O
Cl
 Substitusi Nukleofilik
O O
O
+ Nu LG + LG
LG Nu
Nu
O
LG = Cl , OCCH3 , OCH3 , NH2
best worst
Pembuatan asam anhidrida menggunakan klorida
asam dilakukan tanpa menggunakan katalis
 O
HO
Cl
O
addition
O O H

O
Cl
elimination Cl
O O H

deprotonation O O + HCl

O
Sintesis ester dari klorida
asam
Sintesis amida dari klorida
asam
Amida dari anhidrida