ASAM KARBOKSILAT, ESTER,

Daily Utilization
AMINA DAN AMIDA

Tatanama
Sifat
Sintesisnya (reaksi
pembentukannya))
pembentukannya
Reaksi2 yg terlibat
Spectroscopy

Gugus Karboksil Tatanama

Asam karboksilat mengandung gugus
karboksil pada C no 1.
As. Karboksilat
O IUPAC
|| Common
CH3 COH = CH3COOH
Turunan as. karboksilat
gugus karboksil IUPAC
Common
3

Tentukan rantai terpanjang yg mengandung gugus Formula IUPAC Common

karboksil asam-alkan -oat asam-prefix at
(IUPAC) nomer untuk karbon karboksil 1
(Common) memberikan , , pada atom karbon HCOOH as metanoat as format
yang terdekat dengan karbon karboksil
CH3 CH3COOH ethanoic acid acetic acid
| CH3CH2COOH propanoic acid propionic acid
CH3 CHCH2 COOH CH3CH2CH2COOH butanoic acid butyric acid
IUPAC asam-3-metilbutanoat
Common asam- -metilbutirat

5 6
Give IUPAC and common names:
Carboxylic acids asam lemah
A. CH3COOH
CH3COOH + H2O CH3COO + H3O+
CH3 Neutralized by a base
| CH3COOH + NaOH CH3COO Na+ + H2O
B. CH3CHCOOH

7 8

Sintesis As. Karboksilat Sintesis karboksilat melalui oksidasi

Oksidasi alkohol primer Dari alkohol primer

Oksidasi aldehida Dari aldehida
Oksidasi senyawa aromatik tersubstitusi Dari seny aromatik
Karbonasi reagen Grignard KMnO 4
RCH 2OH RCOOH
or
Hidrolisis turunan asam dan nitril K 2Cr 2 O 7
Reaksi haloform
KMnO 4
Periodic acid Cleavage of Vicinal Dials/Diketones
Dials/Diketones R C H RCOOH
or
Oxidative Cleavage of Alkenes/Alkynes O K 2Cr 2 O 7

KMnO 4
R COOH
or
K 2 Cr 2O 7

Karbonasi reagen
Grignard Hidrolisis turunan asam dan nitril

H+
R C G R C OH + HG
H 2O
O O

O -
OH
R C G R C O - + G-
R C + O O H 2O
O
H+ O
Mg O R C OMgX R C OH
H 2O where G = -X,- OR, - NH 2 , - NHR, -NR 2 , &- O C R
X O
H + or OH - -
RC N R C NH 2 R C OH ( R C O )
H 2O
O O O
 Periodic Acid Cleavage of Vicinal
Reaksi Haloform Dials/Diketones
Dials/ Diketones

Cleavage of methyl carbinols

Cleavage of methyl carbonyls H C C H 2HCOOH + HIO 3
HIO 4
H O O
X2
CH 3 C R - RCOO - + HCX 3 R C C H RCOOH +HCOOH +HIO 3
OH /H 2 O HIO 4
OH O O

X2 R C C R' RCOOH +R'COOH +HIO 3

HIO 4
CH 3 C R - RCOO - + HCX 3 O O
OH /H 2 O
O

Oxidative Cleavage Reactions

Reaksi2 yg terjadi pd as Karboksilat
Alkene Cleavage
Hot Potassium Permanganate
Alkyne Cleavage
Reaksi pembentukan garam karboksilat
Hot Potassium Permanganate
Ozonolysis Rx pembentukan halida asam
Rx pembentukan Ester
Rx pembentukan amida
R CH CH R'
KMnO 4
RCOOH +R'COOH
Rx pembentukan anhidrida asam

Reduksi membentuk alkohol
ozonolysis Dekarboksilasi
R C C R' RCOOH +R'COOH
or
KMnO 4

Pembentukan halida asam

Pembentukan garam karboksilat
Reaction with Active Metals Reaction with Thionyl Chloride
Reaction with Strong Base Reaction with Phosphorus Trichloride
Reaction with Weak Base Reaction with Phosphorus Pentachloride
RCOOH R C Cl + SO 2 + HCl
SOCl 2
O
RCOOH o RCOO - Na + + 1
2
H2
Na
3 RCOOH 3R C Cl + H 3 PO 3
PCl 3
RCOOH RCOO - Na + + H 2O O
Na OH

RCOOH RCOO - Na + + H 2O + CO 2 RCOOH R C Cl + POCl 3 + HCl

Na HCO 3
PCl 5
O
 Pembentukan Ester ((Esterifikasi
Esterifikasi))
From Carboxylic Acids
with ROH via mineral acid catalysis
via the use of diazomethane In ester, the H in the carboxyl group is replaced with
From Acid Chlorides an alkyl group
From Acid Anhydrides
O
R C OH
R'OH
R C OR' + H 2 O ||
+
H
O O CH3 CO CH3 = CH3COO CH3
R C OH R C O CH 2 H +N2
CH 2 N 2
O O
ester group
R'OH
R C Cl R C OR' + HCl
O O
R'OH
R C O C R R C OR' + R C OH
O O O O 20

Name the alkyl from the alcohol O-

Esters give flowers and fruits their pleasant Name the acid with the C=O with ate
fragances and flavors. acid alcohol
O
|| methyl
CH3 CO CH3
Ethanoate methyl ethanoate (IUPAC)
(acetate) methyl acetate (common)

21 22

Flavor/Odor
Give the IUPAC and common names of the
Raspberries following compound, which is responsible for
HCOOCH2CH3 ethyl methanoate (IUPAC) the flavor and odor of pears.
ethyl formate (common)
O
Pineapples ||
CH3CH2CH2 COOCH2CH3 CH3 CO CH2CH2CH3
ethyl butanoate (IUPAC)
ethyl butyrate (common)

23 24
 O
Draw the structure of the following compounds:
||
propyl
CH3 CO CH2CH2CH3 A. 3-bromobutanoic acid

propyl ethanoate (IUPAC) B. Ethyl propionoate

propyl acetate (common)

25 26

A. 3-bromobutanoic acid Reaction of a carboxylic acid and alcohol

Br Acid catalyst
| O
CH3CHCH2COOH || H+
CH3 COH + HOCH2CH3
B. Ethyl propionoate
O O
|| ||
CH3 CH2 COCH2CH3 CH3CH2COOCH2CH3 CH3 COCH2CH3 + H2O

27 28

Esters react with water and acid catalyst Esters react with a bases
Split into carboxylic acid and alcohol Produce the salt of the carboxylic acid and
O alcohol
|| H+ O
H COCH2CH3 + H2O ||
CH3COCH2CH3 + NaOH
O
|| O
||
H COH + HOCH2CH3
CH3CO Na+ + HOCH2CH3
salt of carboxylic acid

29 30
Write the equation for the reaction of propionic O
acid and methyl alcohol in the presence of an || H+
acid catalyst. CH3CH2COH + HOCH3

O
||
CH3CH2COCH3 + H2O

31 32

What are the organic products when A.

methylacetate reacts with O
||
CH3COH + HOCH3
A. Water and an acid catalyst?
B. KOH? O
||
B. CH3CO K+ + HOCH3

33 34

Reaksi Pembentukan Amida Pembentukan anhidrida asam

Direct Conversion of Acids to Amides
Via Dehydration of Carboxylic Acids
From Acid Chlorides
From Acid Anhydrides
Via Reaction of RCOCl with RCOOH
From Esters Via Reaction of RCOCl with RCOONa
NH H O)
RCOOH 3
RCOO - NH 4 + ( 2 R C NH 2 ( H 2O )
2R C OH R C O C R
O
R C Cl + 2 NH R C NH + NH 4 Cl O O O
3 2
O O R C Cl + HO C R' R C O C R ' + HCl
+ O O O
R C O C R + 2NH 3 R C NH 2 + NH 4 O C R O
O O O O
R C Cl + O C R' R C O C R ' + Cl
R C OR' + NH R C NH + R'OH
3 2 O O O O
O O
Formation of Cyclic Anhydrides
Reduksi karboksilat membentuk alkohol
Formation of 5-membered cyclic anhydrides:

O
C
O Lithium Aluminum Hydride reduction
C OH
O + H 2O Diborane reduction
C OH strong heat
C
O
O +
LiAlH 4 H
RCOOH RCH 2 OH
ether H 2O
Formation of 6-membered cyclic anhydrides:

O
(selective reduction of
O
B 2H 6 carboxyl group in
C C RCOOH RCH 2OH preference to carbonyl
OH diglyme
C O + H 2O of aldehydes/ketones)
OH strong heat
C C
O
O

Dekarboksilasi as karboksilat

Thermolysis of beta-diacids
Thermolysis of beta-keto acids
COOH H
C C + CO 2

COOH COOH

COOH H
C C + CO 2

C C
O O