KARBONSAVSZRMAZKOK

Levezets
O
R

OH

Kmiai rokonsg
O
R

H2O

-HX

2H2O

C
OH

-NH3

A karbonsavszrmazkok tpusai
O

O
R

R
O

Cl
R

karbonsavklorid

C
OR

karbonsavszter

O
karbonsavanhidrid
O
R

NH2
karbonsavamid

R C N
karbonsavnitril

Pldk

karbonsavkloridok
CH3COCl

Cl-CO-CO-Cl

acetil-klorid

oxalil-klorid

COCl
benzoil-klorid

karbonsavanhidridek
CH3-CO-O-CO-CH3
ecetsav-anhidrid

CH3-CO-O-CO-C2H5
ecetsav-propionsav-anhidrid

gyrs anhidridek
O

C
O

C
O
ftlsavanhidrid

O
borostynksav-anhidrid

karbonsavszterek

HCOOC2H5

CH3COOCH3

etil-formit

metil-acett

COOC2H5

CH3COO

etil-benzot

fenil-acett

laktonok (gyrs szterek)

O
HO

C
-H2O

C
OH

O
O

O
O

-butirolakton

-valerolakton

karbonsavamidok
CH3
HCONH2
formamid

CH3CO

CONH2

CH3
N,N-dimetilacetamid

benzamid

laktmok (gyrs amidok)

C

O
H 2N

-H2O

C
OH

NH

O
NH
-kaprolaktm
karbonsavnitrilek
CH3CN

CN

acetonitril
benzonitril

A KARBONSAVSZRMAZKOK REAKTIVITSA
Szubsztitci a karbonil-sznatomon
Mechanizmus
O-

O
R

Nu

addci

C
+

NuH
-H+

O-

O
R

-Xeliminci

Nu

Nu

Reaktivits
X- tvoz csoport

savi erssg

Cl- > Q-COO- > QO- > NH2-

HCl > Q-COOH > QOH > NH3

Reaktivitsi sorrend
O

O
R

Cl > R

O
O

O
Q

> R

O
OQ > R

NH2

Reakcitpusok
O
H 2O

"hidrolzis"

OH

karbonsav

O
Q-OH

"alkoholzis"

O
R

C OQ
szter

X +
O
NH3

"ammonolzis"

C NH2
amid

O
QCOOH

"acidolzis"

C O C
anhidrid

A karbonsavszrmazkok hidrolzise
O
CH3

O
Cl +

H2O

CH3

(gyors)

OH +

HCl

O
CH3-CO-O-CO-CH3 + H2O

2 CH3

(melegts)

OH

Az szterek savas hidrolzise

+

O
A)

OH
H2O

OMe

C
+

OMe

OMe

OH2
-H+

O
R

-H+

OH

OH
R

OH

C+

-MeOH

OMe

OH

OH
R

OH H

OH

OtBu

OMe

OH

C
OH

O
B)

H+

Bu

- Bu

rnykolt karbonilcsoportot tartalmaz szterek hidrolzise

O
R

1. cc. H2SO4

OQ

2. H2O

OH

(R: nagy trigny csoport)

Mechanizmus
O

OQ

OQ

O
-Q-OH

R C+
aclium kation

H2O

O
R

OH

-H

OH2

Plda
CH3

CH3
CH3

COOCH3
CH3

"hidr."

CH3

COOH
CH3

Az szterek lgos hidrolzise (elszappanosts)

O-

O
CH3

OCH3 +

OH-

CH3

OCH3

OH

O
CH3

CH3

+ CH3OH

O-

OCH3

OH

Laktonok hidrolzise
O
O

NaOH/H2O
HX

HO-CH2CH2CH2CH2-COONa

Gliceridek hidrolzise
CH2 O

CO

R1

CH

CO

R2

CH2 O

CO

R3

CH2 OH
H2O/NaOH

glicerid

CH

OH

CH2 OH
glicerin

C13H27COOH

mirisztinsav

C15H31COOH

palmitinsav

C17H35COOH

sztearinsav

C8H17-CH=CH-C7H14COOH

olajsav

R1

COONa

R2

COONa

R3

COONa

szappan

Az amidok savas hidrolzise

+

O
R

+
H

OH

NH2

H2O

C
+

NH2

O
R

HOH

OH

-H

NH2

C+

OH

OH

-NH3 (NH4 )

OH

NH3+

C
OH

A nitrilek savas hidrolzise

R

+
H

NH

H2O

NH

HOH
+

-H+

C
O

OH

C
O
amid

NH2

C
OH

NH

A karbonsavszrmazkok alkoholzise
O
CH3

O
Cl + EtOH

CH3

(gyors)

OEt

O
CH3-CO-O-CO-CH3 + EtOH (melegts) CH3

HCl

OEt + CH3

OH

O
+

CH3

OH + EtOH

H
(savkatalzis)

CH3

OEt

+ H 2O

rnykolt karbonilcsoportot tartalmaz karbonsavak alkoholzise

O
R

1. cc. H2SO4

OH

2. QOH

OQ

(R: nagy trigny csoport)

Mechanizmus
O

OH

OH

O
-H2O

R C+
aclium kation

QOH

O
R

OQ

-H

OQH

A karbonsavszrmazkok ammonolzise
O
NH3

O
R

NH2

HX

NHQ +

HX

NQ2 +

HX

QNH2

C
O

Q2NH

O
CH3

O
Cl + 2 NH3

CH3

NH2 + NH4Cl

O
CH3

CH3-CO-O-CO-CH3 + 2 NH3

O
CH3

O
NH2 + CH3

ONH4

O
OEt + NH3

CH3

NH2 + EtOH

Laktmok
NH2
COOH

NH
-H2O

Gyrs anhidridek reakcija ammnival

O

O
CO-NH2
O

2 NH3

hev.

NH

COONH4
O

O
ftlsavanhidrid

ftlimid

Savanhidridek ellltsa
Savkloridok reakcija karbonsavakkal (acidolzis)
O
CH3

O
Cl + CH3

CH3-CO-O-CO-CH3 + HCl

OH

Dikarbonsavak talaktsa gyrs anhidridekk

O
COOH
hevts

COOH

-H2O

O
COOH
COOH

hevts
-H2O

O
O

A karbonsavszrmazkok redukcija
Katalitikus hidrognezs
R

CO

H2/kat.

Cl

H2/kat.

CH2OH

CH2NH2

Redukci LiAlH4-del
R

CO

Cl

CO

CO

CO

OQ

CO

OH

CO

NH2

1. LiAlH4
2. H+

1. LiAlH4
2. H+

CH2OH

CH2NH2

Az szterek savassga
R

CH

COOEt

-H+

CH

pKa > 20

COOEt

H
O

-H

pKa = 9-11

O
C

EtOOC

CH2 COOEt

EtO-

O-

EtOOC

CH

O
C

COOEt

malonszter

H3C

OC

CH2 COOEt

acetecetszter

EtO-

H3C

OC

CH

COOEt

Claisen kondenzci
O
CH3

OEt

Na
-EtOH

CH2 COOEt

CH3

CH2-COOEt

Mechanizmus
O
CH3

OEt

EtO-

O
CH3

CH2

OEt

CH2

EtOH

OEt

CH3

OEt

CH2COOEt

OEt

O
EtOO
CH3

O
CH

OEt

EtOH

+ CH3

CH2COOEt

Acetecetszter szintzisek

CH3

CH2 C

O
CH3

OEt

NaOEt

CH3

O
CH

O
CH

OEt + R

"SN"

CH3

OEt
O

CH

OEt

R
O
CH3

CH

O
hidrol.

OEt

CH3

CH

OH

O
CH3

O
CH

-CO2

OH

CH3

CH2 R

R
Dekarboxilezs
O

O -CO
2
C
C
CH
CH3
O
R

OH
CH3

O
CH

CH3

CH2 R

R1

R1

R2

CH2

CH3

O
CH

R2

CH3

Malonszter szintzisek

EtO

CH2 C

O
EtO

O
OEt

NaOEt

EtO

CH

O
CH

OEt + R

"SN"

EtO

OEt

CH

OEt

R
O
EtO

O
CH

OEt

hidrol.

HO

CH

OH

O
OH

O
CH

OH

-CO2

OH

CH2 R

R
O
R

R1

R1

R2

CH2

OH

O
CH

R2

OH

Sznsavszrmazkok
Levezets
O

HO

OH

H2O

H2O

O
Cl

C Cl +
foszgn

R-NH2

HO

CO

OH

Cl

CO

OEt EtOH

EtOH

NH3

EtO CO OEt
dietil-karbont

H2N CO NH2
karbamid
R

NH

CO

Cl

hev.

R N C O
alkil-izociant