COMPUSI CARBOXILICI

Clasificare i nomenclatur
Dup numrul grupelor caboxil din molecul:
acizi monocarboxilici
acizi dicarboxilici i policarboxilici
Dup natura radicalului organic:
acizi carboxilici satra!i "i aromatici#
acizi carboxilici n$satra!i%
Nomenclatura acizilor carboxilici
I.U.P.A.C.
s&ixl oic
Ml!i acizi or'anici a d$nmiri $mpiric$ intrat$ (n z) comn$) car$ cor$spnd ori'inii "mai al$s *$'$tal$# sa
propri$t+!ilor lor%
Acid formic Acid acetic Acid oxalic Acid valerianic
(furnici) (acetum=oet) (mcris) (valeriana)
Acid butiric Acid benzoic Acid succinic
(grsime) (rina de benzoe) (chihlimbar)
,p+ o alt+ nom$nclatr+ s$ consid$r+ acizii or'anici ca prodi d$ sbstit!i$ &ormal+ a ni -idro'$n din
-idrocarbri c o 'rpar$ caboxil%
Acid metan- Acid benzen- Acid etencarboxilic
carboxilic carboxilic
Radicalii R-CO pro*$ni!i din acizi s$ nm$sc radicali .acil/ i snt tiliza!i la citir$a altor compi or'anici%
Ionii pro*$ni!i din acizi "la ionizar$# i din s+rri sc-imb+ s&ixl .oic/ c .oat/ i ast&$l) carboxill d$*in$
carboxilat, 0COO1%
ACIZII MONOCARBOXILICI SATURAI (I AROMATICI)
Metode de o!i"e#e
a. Metode o$idati%e. O$ida#ea "-alca"ilo# c C221C34 prin barbotar$a a$rli (n para&in+) la 5661536oC)
tiliz7nd dr$pt catalizatori st$arat d$ zinc sa d$ man'an) na&t$nat d$ cobalt sa p$rman'anat d$ potasi%
C8
3
"C8
2
#
2
COO8 C
4
8
9
COO8 8OOC"C8
2
#
2
COO8
8COO8
C8
3
COO8
8OOC COO8 C8
3
"C8
2
#
3
COO8
Acid 4-metil-pentanoic
Acid roenoic
Acid etanoic
C8
2
: C8 COO8 C8
C8
3
C8
2
C8
2
COO8 C8
3
C8
3
COO8
C

R
+

2
C

+

3

+
R
COO8 C8 C8 COO8 8 C COO8 C8
2 9 4 3
=
COO8 n # C8 " C8
COO8 # C8 " C8 C8 # C8 " C8 C8 m # C8 " C8
2 3
m 2 3
cat ; O 2 ; 9
3 n 2 2 2 2 3
2
+
+
!xidarea catenei benzilice c oxi'$n mol$clar) rmat+ d$ tratar$ c <aOBr sa c =MnO>:
!xidarea hidrocarburilor aromatice c cat$na lat$ral+ c =MnO>:
!xidarea alchenelor "*$zi alc-$n$#
!xidarea alcoolilor "*$zi alcooli#
!xidarea aldehidelor i cetonelor "*$zi compi carbonilici# %
b" #etode de hidroliz% Prin -idroliza d$ri*a!ilor &nc!ionali ai acizilor caboxilici "dintr$ car$ ml!i snt prodi
natarali#) r$zlt+ acizi or'anici% R$ac!ia (n m$di alcalin poart+ nm$l$ d$ saonificare% <itrilii din s$ria
ali&atic+ r$zlt+ or din compi -alo'$na!i i cianri alcalin$ "prin m$canism S<2# i pot &i tiliza!i (n ac$st
scop%

Clorra d$ b$nzil B$nzonitril Acid &$nilac$tic
!binerea acizilor aromatici prin int$rm$dil r$ac!i$i Sandm$?$r ar$ loc con&orm r$ac!iilor:
$idroliza esterilor naturali i sintetici condc$ la acizi i alcooli % In pr$z$n!+ d$ alcalii r$zlt+ s+pnri "*$zi
$st$ri#%
c"!binerea acizilor carboxilici rin sintez Acizii carboxilici r$zlt+ din compi or'anom$talici i dioxid d$
carbon ca s+rri) din car$ s$ pn (n lib$rtat$ prin tratar$ c ap+ acidlat+% Ca $x$mpl) ob!in$r$a acidli
pi*alic:
Alc-$n$l$ adi!ion$az+ oxid d$ carbon (n pr$z$n!a <i"CO#> la 2961366oC i 5661266 at%) &orm7nd
int$rm$diari ciclici) din car$ prin d$scompn$r$ c ap+ r$zlt+ acizi caboxilici satra!i"&i"te'a Re((e#% La
r$ac!i$ pot participa i alcooli%
:
Acizii cicloalcancarboxilici s$ ob!in p$ baza #eac!iei Pe#)i" *#. &olosind n d$ri*at di-alo'$nat "c -alo'$ni c
r$acti*itat$ di&$rit+# i $st$r malonic monosodat% In r$ac!i$ poat$ &i tilizat i n d$ri*at mono-alo'$nat i $st$r
malonic sodat c &ormar$a acizilor carboxilici c cat$n+ mai ln'+
R C8 : C8
2
+ CO R C8 C8
2
C
O
8
2
O
R C8
2
C8
2
COO8
R COOR@
8
2
O
R COO8 R@O8
A
COOH H C R CO H C R CH H C
NaOBr O
9 4 9 4 2 9 4
2

O 8 2 CO COO8 8 C 8 C 8 C
2 2 9 4
B O C
9 2 9 4
+ +
COO8 C8 8 C C< 8 C Cl C8 8 C
2 9 4
<8
O 8 2
9 4
=Cl
=C<
2 9 4
3
2


ArCOO8 ArC< X < Ar Ar<8
3
2
o
2
<8
O 8 2
CX
CC<
2
C 9 O
8X ; 8<O
2

+
BrM'O8 COO8 C # C8 "
CCOOM'Br # C8 " 'Br C # C8 " CBr # C8 "
3 3
8 ; 8O8
3 3
CO
3 3
an-idr $t$r
M'
3 3
2
+
+ +
+
BrM'O8 COO8 C # C8 "
CCOOM'Br # C8 " 'Br C # C8 " CBr # C8 "
3 3
8 ; 8O8
3 3
CO
3 3
an-idr $t$r
M'
3 3
2
+
+ +
+
COO8 C8 R # COOR " C8 R # COOR " 8 C : a < RCl
2
CO
RO8 2
O 8 2
2
<aCl
2
2
2
+

+
%inteza anodic $st$ tilizat+ la ob!in$r$a acizilor sp$riori% ,ac+ s$ spn$ sint$z$i ac$tatl d$ poatsi i sar$a
d$ potasi a $st$rli adipic r$zlt+ acid capronic
St#+ct+#,. U"ele (#o(#iet,!i ale ca#o$il+l+i.
Drpa &nc!ional+ caboxil 1COO8) &ormal poat$ &i consid$rat+ ca &iind &ormat+ prin combinar$a
'rp$lor cabonil "> C:O# i -idroxil "1O8#) l$'at$ la ac$lai atom d$ carbon% Sa s$ poat$ consid$ra c+ r$zlt+
dintr1n ortoacid) instabil) prin $liminar$ d$ ap+% R$zlt+ o &nc!i$ tri*al$nt+ r$pr$z$ntat+ prin &orml$l$ I1III%
Ca rmar$ 'rpa EC:O (n carboxil n $st$ ind$p$nd$nt+ "acizii da p!in$ r$ac!ii d$ adi!i$ &a!+ d$ ald$-id$ i
c$ton$# i nici 'rpa O8) p$ntr c+ acizii caboxilici a t$ndin!a d$ a ioniza spr$ d$os$bir$ d$ alcooli%
Aciditatea i constanta de aciditate%
Constante de aciditate entru unii acizi monocarboxilici
+ H
3
O
+ + H
2
O
C
O
O R H C
O
O R
~
9 3
56
B COO8 R C
B O 8 BC COO R C
=a

+
=

=
(R)H C
O
O H
........
.......
O
C
O H
H(R)
Anionul formiat
Acid formic
O
O
1,27A
o
o
1,27A
H C
o
111
o
1,24 A
o
124,9
o
0,95A
o
1,34A
o
124
o
1,08A
H C
O
O H
-
R C
O
O H
R C
O
O H
+
sau R C
O H
O
I II III
A
C8
3
1"C8
2
#
>
1COO8
1RO8
8
2
O
1COOR "C8
2
#
3
C8
2
C8
3
dim$rizar$
1COOR
C8
2
C8
3
2
"C8
2
#
3

Acid capronic
A
12CO
1COOR
12$
1
Anod
1COOR
12=
A
Catod
A
C8
2
COO
1
"C8
2
#
3
C8
2
COO
"C8
2
#
3
"C8
2
#
3
1COOR
C8
2
COO=
C8
3
COO C8
3
COO
1
C8
3
COO=
"dat$ din lit$ratr+#
Acid+l ca#o$ilic -a../-
0
Acidl &ormic
Acidl ac$tic
Acidl btiric
Acidl caprilic
Acidl &$nilac$tic
Acidl b$nzoic
5F)F2
5)F9
5)96
5)GF
>)H6
4)36
Moti%e &t#+ct+#ale ca#e dete#1i", aciditatea ca#o$il+l+i.
In anionl carboxilat r$zltat prin d$protonar$) conI'ar$a p1 $st$ izo*al$nt+%
M+sr+toril$ distan!$lor int$ratomic$ (n anionl carboxilat con&irm+ $'alitat$a l$'+trilor carbon1oxi'$n%
Efectul radicalului asupra aciditii carboxilului%
2#+(ele #e&(i"3,toa#e de elect#o"i "R# micor$az+ aciditat$a prin m+rir$a sarcinii n$'ati*$ p$ carboxilat i
d$stabilizar$a anionli "I#%
2#+(ele at#,3,toa#e de elect#o"i "RJ # m+r$sc aciditat$a prin micorar$a sarcinii n$'ati*$ p$ carboxilat
"$&$ct 0 I# i stabilizar$a anionli "II#% Ac$lai $&$ct s$ mani&$st+ i (n acidl n$disociat
Aciditatea aci'ilo# a#o1atici "acid b$nzoic i acid b$nzoic sbstitit#% Acidl b$nzoic $st$ n acid mai tar$
d$c7t acizii ali&atici c $xc$p!ia acidli &ormic%
Sbstit$n!ii r$spin'+tori d$ $l$ctroni "alc-il# micor$az+ aciditat$a) iar c$i c $&$ct atr+'+tor d$
$l$ctroni m+r$sc aciditat$a "*$zi $&$ct$#% Aa s$ $xplic+ d$ c$ acidl p1nitrob$nzoic $st$ n acid tar$ "$&$ct 0I i
$&$ct d$ conI'ar$ 0K# iar acidl p1-idroxib$nzoic "$&$ct$ 0I i AK# $st$ n acid mai slab (n compara!i$ c
acidl b$nzoic% In acidl b$nzoic orto1sbstitit int$r*in$ efectul steric% Acizii b$nzoici orto1sbstiti!i snt
acizi mai tari d$c7t acidl b$nzoic%
C
O
O
H
C
O
O H H O
O
C
+ +
- -
R C
O
O
R
C
O
O
'
I II
1/2
1/2
-
-
sau

R C
O
O
R C
O
O
R C
O
O
-
-
O
O
C R
R C
O
O H
R C
O
H
O
-
+
R C
O
O
-
+ H
+
&rorieti fizice L$rm$nii in&$riori "C51C55# ai s$ri$i omoloa'$ a acizilor monocarboxilici satra!i snt
sbstan!$ lic-id$ la t$mp$ratra obinit+) iar t$rm$nii sp$riori "(nc$p7nd c C52# snt sbstan!$ solid$%
L$mp$ratril$ d$ topir$ i d$ &i$rb$r$ cr$sc c cr$t$r$a mas$lor mol$clar$ pr$z$nt7nd o alt$rnan!+M r$sp$cti*
acizii c nm+r par d$ atomi d$ carbon s$ top$sc mai ss d$c7t acizii c nm+r impar) (n*$cina!i% In ac$$ai
s$ri$ omoloa'+ t$mp$ratra d$ &i$rb$r$ ar$ o cr$t$r$ r$'lat+% L$rm$nii sp$riori n pot &i distila!i (n *id p$ntr
c+ s$ d$scompn sb pnctl d$ &i$rb$r$% L$rm$nii in&$riori "C51C># snt solbili (n ap+M solbilitat$a scad$ c
cr$t$r$a mas$i mol$clar$% Acizii sp$riori a solbilitat$ limitat+ (n ap+ i snt solbili (n sol*$n!i or'anici%
pnct$l$ d$ &i$rb$r$ al$ acizilor n$sol*ata!i snt sp$rioar$ c$lor al$ alcoolilor i ald$-id$lor) c$$a c$ s$ $xplic+
prin $xist$n!a asocia!iilor mol$clar$ prin pn!i d$ -idro'$n "I#%
a)"&unctele de toire 'n seria omoloag a b)"(emeraturile de fierbere ale acizilor,
acizilor monocarboxilici saturai liniari alcoolilor i aldehidelor cu acelai numr
(acizi grai) C)*C+," de atomi de carbon 'n molecul,saturai,
monofuncionali
%
N#
at. C
.- 4 0 5 6 7 8 ./ .. .9 .: .4 .0
.5 .6 .7
Solbilita1t$ (n
ap+
';566 ml
la 26oC
6)H4G 6)64G 6)659 6)6699 6)6626 6)666F2 6)6662H >)HF
6)2>> 6)624 6)66H3 6)6633 6)6659
Punctele de topire d$pind (n mar$ m+sr+ i d$ a$zar$a mol$cl$lor (n cristal% Mol$cl$l$ acizilor c cat$n$
mai ln'i adopt+ o con&i'ra!i$ plan+ c a$zar$a atomilor (n zi'1za'%
R C
O
O H
.......
H
O
H
H
.......
H
O
.....
..... O
C
O H
R
I
O
O
t
o
0
1 2 3 4 5 6 7 8
40
80
120
160
200
240
C
Alcooli
Aldehide
Acizi
10
t
o
C
100
o
50
o
0
o
50
o
-
1 20
n
In cristal) cat$n$l$ s$ dispn paral$l pr$z$nt7nd (mpac-$t+ri cristalin$ c n'-iri caract$ristic$ i planri d$
cli*aI "datorit+ &aptli c+ radicalii R s$ atra' nmai prin &or!$ Nan d$r Oaals#%
Densitatea acizilor carboxilici saturai $st$ c at7t mai mar$ c c7t masa mol$clar+ $st$ mai mar$% Acizii
ciclici a d$nsitat$ mai mar$ d$c7t c$i aciclici satra!i%
Ca#acte#i&tici &(ect#ale% In U;) acizii carboxilici a*7nd cromo&orl >C:O pr$zint+ b$nzi caract$ristic$ ca i
compii carbonilici%
<" IR, datorit+ conI'+rii) s$ prodc modi&ic+ri &ndam$ntal$ (n natra l$'+trilor C:O i C1O8 din 'rpa
COO8 i ca rmar$ apar propri$t+!i noi) caract$ristic$ 'rp$i carboxil% Ast&$l &r$c*$n!a C:O apar$ la 5FF61
5FH6 cm15 (n acizii n$asocia!i i la 5F5615F>6 cm15 la dim$riM (n ionl carboxilat C:O : 599615466 cm15%
carbonilic$%
C aItorl sp$ctr$lor IR pot &i di&$r$n!ia!i acizii c cat$n+ normal+ "C83COO8 5F25 cm15# i c$i t$r!iari
"C83#31COO8 5F6> cm15#%
In sp$ctr$l$ RMN) protonl carboxilic) d$z$cranat) la mol$cl$ asociat$ d$t$rmin+ absorb!ii la c7mpri
ma'n$tic$ mai mici) la car$ cor$spnd *alori al$ li > 56 ppm " 5615> ppm#% Protonii din pozi!iil$ )
d$z$crana!i d$ *$cin+tat$a c7mpli) apar la 213 ppm) &nc!i$ d$ strctr+% In acidl b$nzoic 'rpa COO8
in&l$n!$az+ (n mod di&$rit protonii din ncl$) ac$tia pr$z$nt7nd d$plas+ri c-imic$ caract$ristic$%
P#o(#iet,!i c=i1ice
R$acti*itat$a 'rp$i carboxil poat$ &i r$pr$z$ntat+ prin sc-$ma
>o#1a#ea &,#+#ilo#% Acizii or'anici r$ac!ion$az+ c -idroxizi) oxizi bazici) carbona!i i amin$ i &orm$az+
s+rri% La acidlar$ c acizi min$rali) s+rril$ ionizat$ pn (n lib$rtat$ acizii carboxilici cor$spnz+tori% S+rril$
acizilor carboxilici sp$riori a o solbilitat$ limitat+ (n ap+ "*$zi a'$n!i t$nsioacti*i i s+pnri#% S+rril$ c
amin$l$) (n &nc!i$ d$ bazicitat$) disociaz+ r$*$rsibil%Acizii carboxilici snt r$zist$n!i &a!+ d$ acizii min$rali%
R CH
2
C
O
O H
sus-
t!tu-
t!"
A#
H a$!% -
CH
3
COOH CH
3
CH
2
COOH (CH
3
)
2
CH COOH
2,08
1,16
2,36
1,21 2,56 &&'
(

Impachetri cristaline
variaz ntre 53
o
si 90
o
&)an %" $)!*a+
,n a$!%u) st"a-!$ 63
o

O
O
O
O O
O
O
O
O
O
O
O O
O
O
O

O
R COOH
Ast&$l c+ acidl ac$tic $st$ dizol*ant (n r$ac!iil$ car$ a loc (n pr$z$n!a acidli cromic%Acizii carboxilici snt
r$zist$n!i i stabili la (nc+lzir$ p7n+ la circa 266oCM $i pot &i distila!i &+r+ d$scompn$r$% La t$mp$ratri mai
ridicat$) acizii i s+rril$ lor pot s&$ri &$nom$nl d$ d$scompn$r$) prin d$carboxilar$%
-eacia de decarboxilare $st$ o sbstit!i$ $l$ctro&il+ "SK5# &a*orizat+ d$ pr$z$n!a (n pozi!ia a nor 'rp$ c
$&$ct$ 0I sa M car$ stabiliz$az+ carbanionl int$rm$diar:
sa
.ecarboxilarea oxidativ "C!"rob 0 5H9G#) ar$ loc (n pr$z$n!a t$traac$tatli d$ plmb c &ormar$a
alc-$n$lor) dp+ rm+torl m$canism:
S+rril$ d$ ar'int s$ d$carboxil$az+ (n pr$z$n!a bromli) r$ac!i$ tilizat+ p$ntr marcar$a c carbon izotopic%
,$carboxilar$a poat$ &i i n proc$s anodic%
?eca#o"ila#ea% R$ac!ia d$ d$carbonilar$ a acizilor or'anici ar$ loc (n pr$z$n!a acidli sl&ric conc$ntrat%
R$ac!ia st+ la baza m$tod$i d$ ob!in$r$ a CO (n laborator%
Red+ce#ea acizilor carboxilici s$ r$aliz$az+ c LiAl8>) la 366oC i 329 at% Mai or s$ r$dc $st$rii "*$zi
$st$ri#%
R COOH
RCHO
RCH
2
OH

(a)$oo)! su&"-!o-!)
(a)%".!%")
C
H
H
R C H
H
-CO
2
H //(OA$)
3
-A$OH
-/(OA$)
2 C
H
H
R C
H
%!'"-!0a-"
R C H
C H H
Alchena
R C H
H
C
H
H
COOH
/(OA$)
4
C
H
H
COO/(OA$)
3
R C H
H
C
H
H
COO
R C H
H
%"s$o'&un"-"
'
-
A$OH
+
C
-
+
+ #aOH
C
O
O#a
Cu/C.!no)!na
CO
2
-
H
2
O
#a
2 4 4
t
9 4
2
t
CO 8 C COO8 8 C
CO R8 COO8 R
o
o
+
+
3 2 >
<aO8
3
2 >
CaO ; <aO8
3
CO <a C8 <a COO C8
CO C8 COO8 C8
+
+
+

<aO8 C8 <a C8 <a COO C8

>
O 8
3
CO
<aO8
3
2
2
+
+

+
2 2
CO A'Br RBr Br RCOOA' + + +
CO O8 C # 8 C " COO8 C # 8 C "
3 9 4
P H4 > SO 8
3 9 4
2
+
Reac!ii @" (o'i!ia . Radicalii -idrocarbona!i din acizii carboxilici satra!i da r$ac!ii d$ sbstit!i$ d$clanat+
&otoc-imic) c radia!ii UN) sa catalitic% Ast&$l) acidl ac$tic condc$ la n am$st$c d$ -alo'$nacizi car$ s$
s$par+ prin distilar$% R$ac!ia ar$ aplica!ii indstrial$%
Aci'ii 1o"oca#o$ilici &at+#a!i i1(o#ta"!i
Acidul formic, ACOOA) a &ost d$scop$rit (n &rnicil$ roii (n s$c% XNII i (n rzici% S$ mai '+s$t$ i in
ac$ d$ brad i d$ pin% Kst$ n lic-id incolor) c miros (n!$p+tor) n iritant p$ntr pi$l$ i mcoas$% Kst$ n acid
tar$ (n compara!i$ c omolo'ii sp$riori% Acidl &ormic s$ ob!in$ prin m$toda M%B$rt-$lot) 5G99) a*7nd la baz+
r$ac!ia dintr$ oxidl d$ carbon i -idroxidl d$ sodi) la 266o C i 59 at) rmat+ d$ tratar$a c acid sl&ric) la
>6oC%
In loc d$ <aO8 s$ poat$ &olosi lapt$ d$ *ar car$ asi'r+ r$'$n$rar$a <aO8%
Acidl &ormic ob!int prin ac$st proc$d$ s$ pri&ic+ prin distilar$% In acidl &ormic 'rpa carbonil
n$&iind l$'at+ d$ n radical or'anic ci d$ -idro'$n poat$ &nc!iona ca o ald$-id+ c propri$t+!i r$dc+toar$) c$$a
c$ s$ obs$r*+ (n r$ac!ia c o sol!i$ amoniacal+ d$ azotat d$ ar'int sa c o sol!i$ alcalin+ d$ p$rman'anat d$
potasi% Acidl &ormic $st$ d$scomps d$ m$tal$l$ din 'rpa platin$i% ,$ as$m$n$a) $st$ d$scomps d$ acidl
sl&ric i d$ radia!iil$ UN%
S+rril$ acidli &ormic s$ d$scompn con&orm r$ac!iilor:
Ultima r$ac!i$ $st$ tilizat+ la -idro'$nar$a l$irilor *$'$tal$ p$ntr ob!in$r$a mar'arin$i% Acidl &ormic ar$
ac!in$ antis$ptic+ &iind acti* &a!+ d$ mc$'airi i $nzim$M $st$ cons$r*ant "6)59P i 512P# p$ntr l$'m$
mrat$ i &rct$% Kst$ tilizat (n t+b+c+ri$ p$ntr d$calci&i$r$a pi$ilor i (n indstria t$xtil+ ca mordant axiliar%
Acidul acetic sa acidl $tanoic) C83COO8) $st$ lic-id "L%&% 55G)9oC#) c miros (n!$p+tor% Acidl ac$tic $st$ o
sbstan!+ polar+ " : 5)F3 ,#% Acidl ac$tic r$zlt+ (n conc$ntra!i$ d$ 3159P prin &$rm$ntar$a oxidati*+ a
sol!iilor $tanolic$ c aItorl bact$riilor) microderma aceti) din a$r% M$toda n$c$sit+ (n m$di d$ &$rm$nta!i$
compi c &os&or i azot ca -ran+ p$ntr bact$rii% Indstrial) acidl ac$tic r$zlt+ p$ cal$ d$ sint$z+) prin
oxidar$a ac$tald$-id$i) &olosind ac$tatl d$ man'an dr$pt catalizator) la 46oC% R$zlt+ acid ac$tic d$
conc$ntra!i$ H91HFP% C al!i catalizatori s$ ob!in$ n am$st$c d$ compon$nt$ car$ s$ poat$ s$para prin distilar$%
R$zlt+ la distilar$a scat+ a l$mnli% Acidl ac$tic an-idr) ob!int prin r$cti&icar$) s$ nm$t$ acid acetic
3lacial "s$ solidi&ic+ la r$c$) la A54)4oC# i $st$ castic% In cantit+!i mici acidl ac$tic $st$ condim$nt i
cons$r*ant "o!$t#% Acetat+l de calci+ s$r*$t$ la cons$r*ar$a p7inii i br7nz$i "6)>15P#% Acidl ac$tic $st$ n
bn sol*$nt% Poat$ &nc!iona ca mordant axiliar (n indstria t$xtil+ "ac$tat d$ almini#% Un$l$ s+rri snt
oxidan!i "Pb"OAc#>#% Acidl ac$tic poat$ &i mat$ri$ prim+ p$ntr ob!in$r$a ac$ton$i% Acidl ac$tic poat$
participa la n$l$ trans&orm+ri c importan!+ bioc-imic+%
HCOO
-
#a
+
2
400
- H
2
COO#a
COO#a
H
2
1O
4
#a
2
1O
4
COOH
COOH
H
2
1O
4
#a
2
1O
4
-
HCOOH
Acid oxalic
C
o
2 3 2
=O8
8 CO = = 8COO +
+
2 2
C 266
2
8 <i CO 2 <i # 8COO "
o
+ +
2 2
Pt
8 CO 8COO8 +
HCOOH
H
2
1O
4
23
CO
CO
2
+ H
2
O
+ H
2
CCOO8 Cl C8COO8 Cl COO8 ClC8 COO8 C8
3
8Cl
Cl
2
8Cl
Cl
2
8Cl
Cl ; UN
3
2 2 2


8COO8 2 <a 8COO 2 <aO8 2 CO 2
> 2
> 2
SO <a
SO 8

+
+
<aO8 2 CaSO SO <a # O8 " Ca
> > 2 2
+ +
Acidul roionic sau roanoic) C83C82COO8) $st$ n lic-id incolor) solbil (n ap+) n$toxic% Ar$ ac!in$
&n'icid+ ca acid i ca sar$ d$ sodi% Propiona!ii d$ natri i d$ calci snt i bni antis$ptici "p7n+ la 6)2P (n
p7in$#% Propionatl d$ calci $st$ n -$mostatic% Acidl propionic s$ tiliz$az+ la ob!in$r$a nor $st$ri ai
c$lloz$i%
Acidul butiric sa n1btanoic C831C821C821COO8) s$ '+s$t$ (n ntl alim$ntar% Sint$tic s$ ob!in$ prin
m$toda .oxo/ sa prin oxidar$a btanalli% S$ poat$ ob!in$ i prin &$rm$nta!ia oxidati*+ "c bact$rii# a
'lcoz$i% Acidl btiric $st$ n lic-id c n miros r$spin'+tor% Kst$ compon$nt al 'r+similor animal$% Kst$
tilizat la ob!in$r$a nor $st$ri ai c$lloz$i) (n &armaci$ i mas$ plastic$% Acidul izobutiric) "C83#2C8COO8)
s$ '+s$t$ (n r+d+cina d$ arnic+ i (n l$iri $t$ric$) ca $st$ri% Acidul izovalerianic "C83#2C81C821COO8 i
al!i izom$ri s$ '+s$sc (n r+d+cina d$ *al$riana officinalis "odol$an# i !ngelica arc#angelica$ ca d$ri*a!i
odoran!i% Acidl ca atar$ "i ca s+rri# ar$ ac!in$ s$dati*+) calmant+%
Acizii monocarboxilici cu catena normal c nm+r par d$ atomi d$ carbon) C>1C22) s$ nm$sc acizi 'rai i
s$ '+s$sc (n natr+ ca $st$ri) "'r+simi) l$iri $t$ric$#% Mai r+sp7ndi!i snt: acidl btiric "C># (n ntl d$ *ac+)
acidl capronic "C4#) acidl caprilic "CG#) acidl caprinic "C56# (n nt d$ *ac+) d$ capr+ i (n n$l$ 'r+simi
*$'$tal$ "nt d$ cocos#) acidl laric "C52# (n ntl d$ cocos i (n &rct d$ da&in "Lars nobilis#) acidl miristic
"C5>#) acidl palmitic "C54#) acidl st$aric "C5G# (n 'r+sim$ $tc% Strctra ac$stor acizi a &ost do*$dit+ prin
sint$z+ i d$'radar$%
,intr$ acizii c nm+r impar d$ atomi d$ carbon) c cat$na normal+) pr$z$n!i (n l$iri $t$ric$ ca $st$ri) poat$ &i
amintit acid+l (ela#3o"ic C83"C82#F 0 COO8) izolat din l$i d$ mcat+ "Pelargonium roseum#%
Ca acizi ciclici s$ m$n!ion$az+ acid+l lactoacilic) C5H) izolat din Lactobacills arabinoss i L% cas$i) c
strctra:
Acidul benzoic) C4891COO8) s$ '+s$t$ (n r+ini *$'$tal$ i balsam) (n tinctra d$ Loll i d$ P$r% Acidl
b$nzoic $st$ o sbstan!+ cristalizat+ (n &oi!$ alb$) str+lcitoar$) car$ sblim$az+ (naint$ d$ topir$% S$ poat$
s$para i prin antr$nar$ c *apori d$ ap+ "L%t% 525)FoC i L%&% 2>H)2oC#% S$ ob!in$ prin oxidar$a tol$nli sa
prin -idroliza &$niltriclorm$tanli "prods s$cndar la clorrar$a tol$nli#% Acidl b$nzoic i sar$a sa d$
sodi s$ pot tiliza ca d$zin&$ctan!i "6)5P#) cons$r*an!i p$ntr alim$nt$ i m$dicam$nt$%
Acidul fenilacetic) C4891C821COO8) $st$ o sbstan!+ cristalin+) incolor+%
Aci'ii di" (et#ol "acizi na&t$nici#) a &ost pi (n $*id$n!+ (n p$troll rom7n$sc d$ c+tr$ C%,%<$ni!$sc i
,%Is+c$sc "5H3G#) (n cantit+!i mici "sb 5P#% Ki snt acizi alc-ilcicloalcancarboxilici "c ciclri d$ 9 i 4
atomi#% S+rril$ lor d$ cobalt i man'an snt catalizatori importan!i) iar s+rril$ d$ sodi s$ tiliz$az+ ca
s+pnri% Unii na&t$na!i "d$ cpr) d$ $x$mpl#) a propri$t+!i &n'icid$%
<m$l$ acizilor dicarboxilici s$ &orm$az+ prin ad+'ar$a s&ixli %&dioic/ la nm$l$ -idrocarbrii c ac$lai
nm+r d$ atomi d$ carbon) c pr$cizar$a pozi!iilor 'rp$lor carboxil% La acizii c mai mlt$ 'rp$ carboxil s$
pn$ s&ixl cor$spnz+tor%
S$ &olos$sc i denumiri empirice) intrat$ (n z ca d$ $x$mpl: acid oxalic) acid di&$nic) acid sccinic)
acid &talic) acid trim$sic
Metode de o!i"e#e
a. #etode oxidative
Ciclo-$xanl s$ oxid$az+ catalitic condc7nd la acid adipic%
CH
2
COOH
CH
3
(CH
2
)
5
CH CH
CH
2
(CH
2
)
9
COOH
o1) m1) p1Xil$nii s$ oxid$az+ c a$r) (n condi!ii catalitic$) c &ormar$ d$ acizi dicarboxilici aromatici "acizii
&talici#% Acidl o1&talic s$ ob!in$ i prin oxidar$a na&tal$nli%
In ltimii ani s1a ps la pnct o m$tod+ $conomic+ p$ntr ob!in$r$a acidli o1&talic pl$c7nd d$ la
b$nzoat d$ sodi i mono$tilcarbonat d$ sodi) la 266oC%
Acid &talic
2licolii (#i1a#i s$ oxid$az+ la acizi or'anici dicarboxilici% ,$ $x$mpl $til$n'licoll s$ oxid$az+ la acid
oxalic%
Ciclo=e$a"ol+l se oxideaz c p$rman'anat d$ poatsi sa c acid azotic &orm7nd acid adipic) c randam$nt
bn%
Co1(+Bii ca#o"ilici ciclici &a+ dica#o"ilici s$ pot oxida la acizi dicarboxilici% Oxidar$a 'lioxalli ca i a
altor diald$-id$ condc$ la acizi dicarboxilici
Acid oxalic
b" #etode de hidroliz% ,$ri*a!ii di&nc!ionali) (n sp$cial dinitrilii ali&atici) -idroliz$az+ or la acizi
dicarboxilici satra!i% M$toda s$ aplic+ i p$ntr ob!in$r$a acizilor policarboxilici) ca d$ $x$mpl acidl
tricarbalilic "5)2)3 0 propantricarboxilic#%
Acid
tricarbalilic
c" %inteze de acizi dicarboxilici cu a/utorul esterului malonic%
Cond$nsar$a $st$rli malonic c m$tanal "C82O#) -idroliza prodsli int$rm$diar rmat+ d$
d$carboxilar$) $st$ o m$tod+ d$ sint$z+ p$ntr acidl 'ltaric%
St#+ct+#a. P#o(#iet,!i ca#acte#i&tice
Drpa carboxil ar$ strctra $l$ctronic+ id$ntic+ c c$a d$scris+ la acizii monocarboxilici%
Pr$z$n!a c$lor do+ 'rp$ carboxil in&l$n!$az+ aciditat$aM
Acizii dicarboxilici satra!i snt mai tari d$c7t acizii monocarboxilici%
(ROOC)
2
CH
2
+H
2
C(COOR)
2
-
H
2
O
(ROOC)
2
CH CH
2
CH(COOR)
2
(HOOC)
2
CH CH
2
CH(COOH)
2
HOOC CH
2
CH
2
CH
2
COOH
-2 CO
2
H
2
O
- 4 ROH
CH
2
O
+
a$!% 4)uta-!$
CH
2
CH CH
2
C) C) C)
3
-3
#aC#
#aC)
CH
2
CH CH
2
C# C# C#
H
2
O
#H
3
6
-3
CH
2
CH CH
2
COOH COOH COOH
CHO
CHO
5O6
COOH
COOH
OH
H
5O6 O 5O6
COOH
COOH
OH
COO
-
#a
+
#aOCOOC
2
H
5
/
50 7
200
o
COOH
COOH
C
C
COOH
COOH
400
o
O
2
/3
2
O
5
/
C8
3
C8
3
a$!% a%!&!$
$!$)o."8an
O
2
95
o
s9-u-! %" Co COOH
COOH
acid &talic
Ki disociaz+ (n do+ tr$pt$%
K&$ctl indcti* "1I# al 'rp$lor carboxil s$ mani&$st+ prin cr$t$r$a constant$i (n prima tr$apt+ d$ ionizar$% In a
doa tr$apt+ d$ ionizar$) (n '$n$ral) =2 $st$ mai mic+%
In '$n$ral =2 $st$ mai mic+ d$c7t =5 c c$l p!in n ordin d$ m+rim$ datorit+ r$plsi$i $l$ctrostatic$%
Qac$ $xc$p!i$ acidl oxalic) car$ ar$ o aciditat$ m+rit+ "p=5 : 5)2F i p=2 : >)2F# datorit+ mani&$st+rii
$&$ctli 0I al prim$i 'rp$ carboxil &a!+ d$ a doa d$ car$ $st$ l$'at+ dir$ct "5)2#%
Constantele de aciditate i solubilitatea unor acizi dicarboxilici
"dat$ din lit$ratr+#
Acidul -.../-0 -9../-5 Sol+ilitate @"
a(,
La 9/o C @" C
Acidl oxalic 9H66 4> G)4
Acidl malonic 5>H)6 2)6 F3)9
Acidl sccinic 4)> 3)3 9)G
Acidl 'ltaric >)9 3)G 43)H
Acidl adipic 3)G 3)H 5)9
Acidl pim$lic 3)3 3)G 9)6
Acidl sb$ric 3)6 >)6 6)54
Acidl ac$laic 2)G >)6 6)2>
Acidl s$bacic 2)F 2)9 6)56
Acidl &talic 525 1 6)56
Acidl oxalic an-idr cristaliz$az+ di&$rit) sa ) (n &nc!i$ d$ modl d$ &ormar$ a l$'+trilor d$ -idro'$n%
!cizii dicarboxilici sp$riori) d$ la patr atomi (n ss) c nm+r par d$ atomi d$ carbon) a mol$cl$l$ plan$ i
c$ntrosim$tric$) (n timp c$ la acizii c numr impar mol$cl$l$ snt n$plan$) r+scit$ c o ax+ d$ sim$tri$
binar+M 'rp$l$ carboxil snt (nclinat$ c n n'-i d$ 46o% Mol$cl$l$ acizilor c nm+r impar d$ atomi d$
carbon snt mai bo'at$ (n $n$r'i$ d$c7t acizii din s$ria par+ i ast&$l s$ pot $xplica di&$r$n!$l$ pnct$lor d$
topir$ sa solbilitat$a%
C C
O
OH
O
O
H O
H O
C C
O
HO
HO
C
O
C
O
O H O
C
O
H O
C C
O
O
HO
H O
C
O H
C
O
OH
C
HO
O
acid oxalic
acid oxalic
HOOC (CH
2
)
n
COOH
+
H
2
O
:
1
+
HOOC (CH
2
)
n
COO
-
H
3
O
+
P#o(#iet,!i Di'ice Acizii dicarboxilici snt solizi) ca rmar$ a nm+rli mar$ d$ l$'+tri d$ -idro'$n
int$rmol$clar$%
Te1(e#at+#ile de to(i#e &cad c cr$t$r$a mas$i mol$clar$ i pr$zint+ alt$rnan!+: acizii c nm+r par d$
atomi d$ carbon a pnct$ d$ topir$ mai mari d$c7t acizii din s$ria impar+% Pnct$l$ lor d$ topir$ r+m7n
sp$rioar$ c$lor al$ acizilor monocarboxilici%
P#o(#iet,!i c=i1ice
P#o(#ietatea (#i"ci(al,) car$ !in$ d$ pozi!ia r$ciproc+ a c$lor do+ 'rp+ri carboxil $st$ comportarea
la 'nclzire sau descompunerea termic%
+
H
2
O
C CH
2
O
O
O
CH
2
C CH
2
COOH CH
2
CH
2
COOH
CH
2
+
H
2
O
COOH CH
2
CH
2
CH
2
C
C
O
O
O
CH
2
COOH
+
CO
2
CH
3
COOH 5CH
2
C
OH
OH6
CO
2
-
-
160 140
C
O
O
H
C O
O
CH
2
H
o o
C
H
2
O
+
+ CO CO
2
CO
2
+
HCOOH
H
2
1O
4
4)!$"-!na
200
o
150
o sau
COOH
COOH
C
t
o
C
20 1
100
o
120
o
140
o
160
o
180
o
126
120
114
109
a
o
o
o o
Aci'i dica#o$ilici i1(o#ta"!i
Acidul oxalic $st$ r+sp7ndit (n natr+ ca sar$ d$ m+cri) oxalat acid d$ potasi sa ca sar$ d$ calci% Lib$r s$
'+s$t$ (n Asp$r'ills ni'$r% Oxalatl d$ calci s$ d$pn$ sb &orm+ d$ calcli (n litiaz$% Acidl oxalic $st$
toxic% S$ poat$ ob!in$ prin oxidar$a nor compi or'anici) $til$n'licol) 'lcoza $tc% ,in pnct d$ *$d$r$
c-imic) acidl oxalic $st$ n r$dc+tor%P$ ac$ast+ propri$tat$ s$ baz$az+ tilizar$a acidli oxalic ca d$colorant
(n indstria t$xtil+ i (n c-imia analitic+% Sar$a d$ m+cri "=8C2O>%82C2O>%282O# $st$ &olosit+ la scoat$r$a
p$t$lor d$ r'in+%
Acid+l 1alo"ic) acid 5)31dicarboxilic) s$ '+s$t$ ca sar$ d$ calci (n s&$cla d$ za-+r%
S$ ob!in$ prin trans&ormar$a monoclorac$tatli d$ sodi (n nitril) rmat+ d$ -idroliz+% Atomii d$
-idro'$n din 'rpa C82 din mol$cla acidli malonic "plasat+ (ntr$ 'rp$l$ carboxil# snt acti*i) particip+ la
mlt$ r$ac!ii (n &olosl sint$z$i or'anic$% Acidl malonic s$ d$carboxid$az+ or) d$ ac$$a propri$t+!il$ snt
stdiat$ p$ di$st$r%
Reac!iile e&te#+l+i 1alo"ic !binerea esterului malonic sodat" Prin tratar$a $st$rli malonic c di&$ri!i
a'$n!i bazici (n m$di an-idr ar$ loc &ormar$a malonatli% ,$ $x$mpl) sb ac!in$a $tilatli d$ sodi) a
sodili m$talic sa a amidrii d$ sodi r$zlt+ $st$r malonic sodat%
Anionl $st$rli s$ r$pr$zint+ prin &orml$ limit+ sa strctr+ m$zom$r+: I)II sa III% In c$l$ mai mlt$ r$ac!ii
$st$rl sodat s$ comport+ ca i cm ar a*$a &ormla I) d$i &ormla r$al+ $st$ III) (n car$ $xist+ n sist$m
conI'at c r$partizar$a ni&orm+ a $l$ctronilor p$ cinci atomi%
(ulte sinteze a ca sbstan!+ d$ pl$car$ $st$rl malonic sodat sa $st$rl ca atar$%
C CH C O
OR OR
O
-
1
,,
2 ,, ,
-
O C CH C
OR OR
O
-
-
O C CH C O
OR OR
sau
,,,
+
-
-

O C
CH
C O
OR
OR
#a
+
-
ROOC CH COOR
+
-
C
2
H
5
O #a
ROOC CH
2
COOR
+
H
2
O
CO
2
2
5O6
COOH
COOH
C
140-150
o
(CH
2
)
5
COO
-
COO
-
Ca
++
CaCO
3
O +
t
o
+ + H
2
O CO
2
H
2
C
CH
2
H
2
C
CH
2
CO
H
2
C CH
2
COOH
H
2
C CH
2
COOH
H
2
O +
C
C
O
O
O
COOH
COOH
Kst$rl malonic sodat particip+ la ob!in$r$a acizilor monocarboxilici satra!i liniari) ciclici) a acizilor
dicarboxilici satra!i sa a acizilor n$satra!i% Ob!in$r$a acizilor monocarboxilici satra!i liniari:
(diacid instabil) Acid roanoic
Acid+l &+cci"ic $st$ n acid 5)>1dicarboxilic% S$ '+s$t$ (n cantit+!i mici (n or'anism$l$ *ii i (n cantit+!i mari
(n c-i-limbar "sccinm#% S$ ob!in$ prin -idro'$nar$a acidli mal$ic%
Sb &orm+ d$ an-idrid+ int$r*in$ ca acidlant (n prods$l$ alim$ntar$% Kst$rii s+i) ca mono'lic$rid$)
(mbn+t+!$sc calit+!il$ prods$lor d$ pani&ica!i$% Acidl sccinic i nii d$ri*a!i alc+ti$sc mat$ria prim+ (n
sint$za or'anic+%
Acid+l adi(ic) 5)41dicarboxilic) s$ ob!in$ indstrial prin oxidar$a ciclo-$xanon$i sa ciclo-$xanolli c acid
azotic sa p$rman'anat d$ potasi% Prin policond$nsar$ c diamin$ ali&atic$ &orm$az+ poliamid$ din car$ s$
ob!in &ir$ i &ibr$ sint$tic$ "*$zi poliamid$#% Unii $st$ri ai acidli adipic snt bni plasti&ian!i%
Acid+l &eacic) 5)561dicarboxilic) r$zlt+ prin d$scompn$r$a l$ili d$ ricin) (n m$di alcalin M ricinol$atl
d$ la -idroliz+ tr$c$ (n 21octanol i sar$a monosodic+ a acidli s$bacic% Unii $st$ri ai acidli s$bacic snt bni
plasti&ian!i p$ntr mas$ plastic$%
Aci'ii ciclici dica#o$ilici% Acidl 5)21ciclopropan1dicarboxilic pr$zint+ izom$ri$ cis1trans "R1K#% Acidl cis
"R# $st$ inacti* prin analo'i$ strctral+ c acidl m$zotartric) iar acidl trans "K# s$ pr$zint+ ca rac$mic
"ac$$ai con&i'ra!i$ ca acizii A i 0 tartrici#%
Aci'i a#o1atici dica#o$ilici
Acidul o-ftalic s$ ob!in$ prin oxidar$a o1xil$nli sa na&tal$nli% Acidl &talic $st$ o sbstan!+
cristalizat+) alb+) c L%t%26Go "t$mp$ratra n $st$ n$t+ din caza &orm+rii an-idrid$i#% Kst$ mat$ri$ prim+ p$ntr
indstria coloran!ilor i mas$lor plastic$%
Acid+l te#eDtalic $st$ 'r$ solbil (n sol*$n!i or'anici% Sblim$az+ la 366oC% Kst$ mat$ri$ prim+ p$ntr &ibra
sint$tic+ t$ril$n%
Acizi tricarboxilici i olicarboxilici
Acid+l t#ica#alilic "5)2)31propan1tricarboxilic# a &ost id$nti&icat (n n$l$ *$'$tal$%
O cal$ d$ sint$z+ $st$ saponi&icar$a trinitrilli cor$spnz+tor) ob!int din 5)2)31tribrompropan%
- 3
6
#H
3
H
2
O CH
2
CH CH
2
COOH
COOH
COOH
CH
2
CH CH
2
C# C# C#
HOOC
COOH
H H H
COOH H
HOOC
cis
trans
CH
3
(CH
2
)
5
CH(OH) CH
2
CH CH (CH
2
)
7 COO<a CH
3
(CH
2
)
5
CH
3
CH(OH)
H
2
O
(CH
2
)
8
COO#a HOOC +
2-Octanol Sarea monosodic a
acidului sebacic
HC COOH
COOH HC
H
2
/ #!
H
2
C COOH
COOH
H
2
C
2 -
CH
3
CH
2
COOH
CO
2
CH
3
CH(COOH)
2
-
-
2
ROH
H
2
O
CH
3
CH(COOR)
2
#aC)
CH
3
C)
+
-
+
#a CH(COOR)
2
Acid+l t#i1e&ic) 5)3)91b$nz$ntricarboxilic) ca i c$ilal!i izom$ri) s$ pr$par+ prin oxidar$a trim$tilb$nz$nilor
cor$spnz+tori:
#ezitilen Acid trimesic $emimeliten Acid hemimelitic acid melitic
Acid+l 1elitic) b$nz$n1-$xacarboxilic) s$ &orm$az+ prin oxidar$a 'ra&itli) a c+rbnilor &osili sa
c+rbn$li acti* c acid azotic% R$ac!ia con&irm+ pr$z$n!a in$l$lor b$nz$nic$ (n 'ra&it% La distilar$ c calc$
sodat+ s$ d$carboxil$az+ condc7nd la b$nz$n% Acidl m$litic $st$ sbstan!+ solid+) stabil+) or solbil+ (n ap+%
Acid roenoic Acid cis-0-octadecenoic
Acid acrilic Acid oleic
Metode de o!i"e#e a aci'ilo# "e&at+#a!i 1o"oca#o$ilici
a. #etode de eliminare"
1liminarea aei din 1-idroxiacizi (n m$di acid d$cr'$ or) as$m+n+tor d$s-idrat+rii alcoolilor) con&orm
sc-$m$i:
?e=id#o=alo3e"a#ea acizilor 1-alo'$na!i (n m$di d$ =O8 alcoolic
b% Metode o$idati%e @" ca#e o$ida"t+l "+ le'ea', d+la le3,t+#,
Oxidar$a bl7nd+ a n$i ald$-id$ n$satrat$ c oxid m$d d$ ar'int sa c oxidaz$ condc$ la acid n$satrat%
c" #etode de condensare
P$ntr a ob!in$ acizi )1n$satra!i sa c l$'+tri dbl$ conI'at$ s$ aplic+ cond$nsar$a ald$-id$lor
cor$spnz+toar$ c acid malonic (n pr$z$n!+ d$ piridin+ sa pip$ridin+%
Acid ,-nesaturat
2n acelai mod ot s rezulte i unii acizi cu mai multe duble legturi3 de exemlu acid sorbic
R CHO+ H
2
C(COOH)
2
/;
H
2
O
-
R CH C(COOH)
2
CO
2
R CH CH COOH
-
R CH CH CHO
A4
2
O
R CH CH COOH
R CH CH
2
COOH
H
C)
R CH CH
2
COOH
C)
-
OH
H
2
O
-
C)
-
R CH CH COOH
-
-
HO H
2
C CH
2
COOH
H
+
H
2
O
-
CH
2
CH COOH
CH
3
(CH
2
)
7
C C
H
H
(CH
2
)
7
COOH
H
2
C CH COOH
CH
3
H
3
C
CH
3
5O6
HOOC
COOH
COOH
sau
CH
3
CH
3
CH
3
COOH
COOH
COOH
5O6
COO8
COO8
COO8
8OOC
8OOC
COO8
Ald$-ida b$nzoic+) (n condi!iil$ reaciei &er4in) s$ cond$ns$az+ ca an-idrid+ ac$tic+ (n pr$z$n!a ac$tatli d$
sodi "baza# c &ormar$a acidli cinamic% ,p+ ac$st m$canism) s$ pot ob!in$ i al!i acizi%
St#+ct+#a. P#o(#iet,!i Di'ice. Ca#acte#i&tici &(ect#ale
R) $st$ n$satrat: *inil1alil1) $tinil1 $tc%
Radicalii or'anici n$satra!i snt 'rp$ atr+'+toar$ d$ $l$ctroni) c $&$ct 0I ca i -alo'$nii) car$ m+r$sc
stabilitat$a anionli carboxilat i d$ci) m+r$sc aciditat$a acidli r$sp$cti*% P$st$ $&$ctl indcti* s$ sprapn$
$&$ctl d$ conI'ar$) car$ ac!ion$az+ anta'onist c $&$ctl 0I) tinz7nd s+ micor$z$ par!ial aciditat$a%
Constante de aciditate
?e"+1i#ea >o#1+la -a../-0
Acid acrilic 82C:C81COO8 9)4
Acid *inilac$tic 82C:C81C821COO8 >)42
Acid crotonic C831C8:C81COO8"R# 2)6>
Acid cinamic C4891C8:C81COO8 2)49
Acid t$trolic C831CSC1COO8 222)G
Acizii n$satra!i snt acizi mai tari d$c7t acizii satra!i)
,atorit+ dbl$i l$'+tri) nii acizi n$satra!i apar) d$ c$l$ mai mlt$ ori) sb &orma izom$rilor '$om$trici cis1
trans%
Izom$rii trans s$ '+s$sc (n natr+ (n cantit+!i mai miciM (n cantit+!i mai mari s$ &orm$az+ la -idroliza 'r+similor
sa prin sint$z+) prin r$ac!ii d$ $liminar$M n snt asimila!i d$ or'anism% Acizii cis snt mai r+sp7ndi!i) mai
stabili i int$r*in (n proc$s$l$ bioc-imic$% Unii acizi n$satra!i apar (n natr+ ca sbstan!$ l$ioas$) al!ii (n star$
solid+%
I" U;) 'rpa carboxil ar$ $&$ct batocrom in&l$n!7nd tranzi!iil$ 1T din sist$ml n$satrat%
In sp$ctr$l$ IR acizii ) 1n$satra!i pr$zint+ o &r$c*$n!+ caract$ristic+ C:C car$ apar$ la 543615446 cm15 M
c$l$lalt$ &r$c*$n!$ C:O i O18 apar) c mici d$plas+ri) (n dom$niil$ caract$ristic$ acizilor satra!i%
In sp$ctr$l$ RMN protonii *inilici snt pt$rnic d$z$crana!i "acizi )1n$satra!i# a*7nd d$plas+ri c-imic$
caract$ristic$%Protonl carboxilic apar$ la 5315> ppm%
CH
3
CH CH COOH CH CH COOH
C
6
H
5
&&'

7,10 5,83 13,18

7,83 6,46 13,21
+
-
R CH CH C OH
O
R CH CH C OH
O
R C O
O
H
acid cinamic
COOCOCH
3
H
2
O
C
6
H
5
CH CH
-
H
2
O
C
6
H
5
CH COOH CH + CH
3
COOH
CH
3
COOCOCH
3
+
< =
-
C
6
H
5
C
O
H
+
3,01 A
3,77 A
st-u$tu-a $!s
st-u$tu-a t-ans
1,33A
1,33A
P#o(#iet,!i c=i1ice
Acizii or'anici n$satra!i particip+ la r$ac!ii prin 'rpa carboxil c &ormar$ d$ s+rri i d$ri*a!i &nc!ionali%
Qiind acizi carboxilici n$satra!i da (ns+ i r$ac!ii "c$l$ mai mlt$# caract$ristic$ sist$mli n$satrat%
!diia d$ -idro'$n mol$clar (n pr$z$n!a d$ catalizatori "<i) Pd) Pt# sa d$ -idro'$n (n star$ n+sc7nd+)
c$l mai or r$ac!ia ar$ loc la dbla l$'+tr+%
Reacia este util te#nologiei de #idrogenare a uleiurilor )egetale pentru obinerea margarinei
Adi!ia -alo'$nli $st$ na din r$ac!iil$ caract$ristic$% Adi!ia I2 s$r*$t$ la caract$rizar$a 'radli d$
n$satrar$ prin ci&ra d$ iod "indic$ d$ iod#% La acizii c dbl$ l$'+tri conI'at$) s$ &orm$az+ prodsl d$ adi!i$
la cap$t$l$ sist$mli) c o dbl+ l$'+tr+ $cranat+ "d$ -alo'$n i d$ 'rpa COO8#) car$ n s$ mai poat$
-alo'$na "$&$ct cc+#%
Cu ozonul) acizii n$satra!i &orm$az+ ozonid$ "ca i alc-$n$l$#) car$ prin d$scompn$r$ da compi c cat$n$
mai scrt$) c strctra cnosct+) r$ac!ia s$r*ind la d$t$rmin+ri strctral$% C oxi'$nl mol$clar) acizii
n$satra!i) (n sp$cial c$i sp$riori) s$ atooxid$az+ (n pozi!i$ alilic+ '$n$r7nd $poxizi) -idroxiacizi sa s$
p$roxid$az+ i s$ d$'rad$az+ %
Degradarea grsimilor ar$ loc (n proc$sl d$ pr$lcrar$ i (n timpl p+str+rii) sb ac!in$a lminii) a *aporilor
d$ ap+ "miditat$#) a c+ldrii) (n contact c a$rl "oxi'$nl# sa (n pr$z$n!a nor microor'anism$) c apari!ia
mirosli d$ alt$rar$) 'stli sp$ci&ic n$pl+ct i c cr$t$r$a acidit+!ii%Q$nom$nl d$ d$'radar$ "r7nc$zir$#
poat$ &i o r*ncezire #idrolitic sb in&l$n!a m$z$lii sa a lipaz$lor c &ormar$a acizilor 'rai lib$ri i dr$pt
rmar$ cr$t$ aciditat$a "indic$ d$ aciditat$# 'r+simii% R*ncezirea cetonic const+ (n oxidar$a acizilor
'rai sb in&l$n!a $nzim$lor sa a oxi'$nli c &ormar$a acizilor 1c$tonici car$ imprim+ 'st n$pl+ct) it$%
Prin d$carboxilar$) acizii tr$c (n c$ton$ car$ con!in n radical m$til) *olatil$ i toxic$% Ac$ast+ r7nc$zir$
c$tonic+ condc$ la modi&ic+ri d$ 'st i la miros n$pl+ct% ,$'radar$a $st$ acc$ntat+ la 'r+simil$ car$ con!in
acizi 'rai c 4152 atomi d$ carbon%
R$ac!iil$ s$ p$tr$c dp+ sc-$ma:
Adi!ia co1(+Bilo# "e&i1et#ici ar$ loc contrar r$'lii li MarUo*niUo* d$oar$c$ ori$ntar$a adi!i$i $st$
d$t$rminat+ d$ $&$ctl atr+'+tor d$ $l$ctroni al 'rp$i COO8 aspra l$'+trii 08C:C81
R CH
2
CH
2
COOH
o8!%a-"
R C CH
2
COOH
O
COO8 R C8
3
COO8
8
2
O CO
2
-
+ R C C8
3
O
oxoacid
R CH CH CH CH COOH +
,
2
R CH
CH CH
CH
I
I
COOH
I
2
-
-
-
-
-
-
R COOH CH
2
CH
2
H
2
/ $at
R CH CH COOH
I'o1e#i'a#ea% La (nc+lzir$a acizilor n$satra!i c dbl+ l$'+tr+ (n pozi!ii d$p+rtat$ d$ carboxil ")M ) i )
#) (n pr$z$n!a baz$lor pt$rnic$) s$ prodc d$plas+ri al$ dbl$i l$'+tri (n )%
Elaidi'a#ea - poat$ &i consid$rat+ o r$ac!i$ d$ izom$rizar$% Acidl ol$ic "cis# (n pr$z$n!a rm$lor d$ acid azotos
"<O2T# sa a raz$lor UN) tr$c$ (n acid $laidic "trans#%
Lacto"i'a#ea
,ac+ acizii n$satra!i con!in dbla l$'+tr+ (n pozi!ia )1 sa (n )1) 'n mediu acid$ ar$ loc o int$rac!i$ dbla
l$'+tr+ 0 'rpa carboxil) c &ormar$a ni $st$r ciclic d$nmit lactona%
Analo' s$ &orm$az+ 1 lactona :
*a)"-o)a$tona
CH
3
CH CH
CH
2
COOH
H
+
H
3
C CH CH
2
O H CH
2
C
O
H
3
C CH CH
2
O
CH
2
C
O
H
+
+ -
CH
3
(CH
2
)
7
CH
HC
(CH
2
)
7
COOH
#O
2
>/ (23)
CH
3
(CH
2
)
7
CH
HOOC CH (CH
2
)
7
acid ol$ic1cis acid $laidic1trans
sbstanta lic-ida natrala
sbstanta solida d$ sint$za
CH
3
CH CH CH
2
COOH
OH / t
o
C
H
2
O
CH
3
CH CH CH COOH
-
-
-
+ R CH CH COOH
H<- R CH CH
2
COOH
<-
R CH CH
2
COOH
OH
R CH CH
2
COOH
C#
HC#
H
2
O
-
CH
3
CH CH CH COOH
sau
CH CH CH
3
CH COOH
-
H
2
O
HO
-
CH
3
CH
2
CH CH COOH
R CH CH CH
2
CH CH COOH
HO / t
o
-
R CH
2
CH CH CH CH COOH
In condi!ii sp$cial$) prin &i$rb$r$ (n alcalii) acizii n$satra!i pi$rd dioxidl d$ carbon c &ormar$a alc-$n$lor
cor$spnz+toar$%
Aci'i "e&at+#a!i 1o"oca#o$ilici 1ai i1(o#ta"!i
Acidul metilacrilic $st$ n lic-id car$ polim$riz$az+ or% Kst$rl s+ m$tilic $st$ monom$rl
sticl$i pl$xi) .sticla or'anic+/ car$ ar$ o transpar$n!+ &oart$ bn+ i o mas+ mol$clar+ mar$%
R$ac!ia ar$ la baz+ ac$tona i acidl cian-idric% In sol!i$ d$ 82SO> conc$ntrat ar$ loc -idroliza i (n
ac$lai timp d$s-idratar$a%
In sol!i$ d$ 82SO> conc$ntrat i alcool m$tilic) p$ l7n'+ saponi&icar$ i $liminar$ d$ ap+) ar$ loc $st$ri&icar$a%
M$tacrilatl d$ m$til s$ polim$riz$az+ dp+ m$canisml radicalic) (n bloc) la 529oC) c &ormar$a
polim$tacrilatli d$ m$til%
Acid+l at#o(ic r$zlt+ la d$'radar$a prods$lor *$'$tal$ nd$ s$ '+s$t$ sb &orma cond$nsat+%
Acidul crotonic) 1m$tilacrilic) s$ pr$zint+ ca izom$ri cis1trans "R1K#% S$ ob!in$ prin sint$z+ "*$zi m$tod$
'$n$ral$ d$ pr$parar$#% Acidl crotonic 0trans $st$ o sbstan!+ solid+ stabil+ "izom$rl cis $st$ lic-id)
L%&%:54HoC#% Prin oxidar$) acidl crotonic tr$c$ (n acid oxalic i acid ac$tic "con&irm+ strctra#) iar prin
-idro'$nar$ dc$ la acid btiric%
"L%t:F2
o
C#
"L%t:59
o
C#
acid crotonic1trans acid izocrotonic1cis
CH
3
C H
C HOOC H
CH
3
C H
C COOOH H
23
130
C
o
acid atropic "1 &$nilacrilic#
H
2
C C COOH
C
6
H
5
#H
4
H1O
4
+ H
2
C C
CH
3
COOCH
3
H
2
1O
4
CH
3
OH +
CO#H
2
+
-
H
2
O
H
2
O
CH
2
C
CH
3
CH
3
C
CH
3
OH
C#
H
2
1O
4
CH
2
C
CH
3
C#
CH
3
C
CH
3
OH
C#
CH
3
C
CH
3
OH
H
2
1O
4
COOH
H
2
O/H
+
-
CH
2
C
CH
3
COOH
CH
3
C O
CH
3
CH
3
C
CH
3
OH
C#
+HC#
:
2
CO
3
H (
- 8,5 :$a)
1<8
3 8
2
O
CH CH
2
?!"-"-"/ a)$a)!!
CH CH COOH C
6
H
5 C
6
H
5
Stiren
R CH CH COOH
?!"-"-"/ a)$a)!!
R CH CH
2
Alchena
H
+
CH
3
CH CH
CH
2
CH
2
COOH H
3
C CH
CH
2
H
3
C CH
CH
2
CH
2
CH
2
O
C
O
+ -
CH
2
CH
2 O
C
O
H
H
+
)a$tona, !n a&a
-"?a$" a$!%u) satu-at
Acidl *inilac$tic) C82:C81C821COO8) $st$ instabil i (n m$di acid sa bazic s$ izom$riz$az+ (n acid
crotonic
Acidul cinamic) C4891C8:C81COO8) s$ '+s$t$ (n natr+ ca $st$r (n n$l$ r+ini i balsamri% Un l$i d$
scor!ioar+ s$ '+s$t$ lib$r ca izom$r trans "K#% Izom$rl cis "R# $st$ nmit acid alocinamic i s$ '+s$t$ (n
natr+ nmai ca $st$r% Acidl cinamic s$ ob!in$ prin sint$za din ald$-ida b$nzoic+ i an-idrida ac$tic+) (n
cataliza bazic+ "*$zi cond$nsar$a P$rUin#% Acidl alocinamic s$ &orm$az+ din acid cinamic prin ilminar$ UN%
Prin -idro'$nar$ acizii cinamic i alocinamic condc la ac$lai acid 1&$nilpropionic sa -idrocinamic%
Prin cicloadi!i$ sb ac!in$a lminii) acidl cinamic tr$c$ (n acizii trxilic i trxinic car$ a &ost izola!i i din
&rnz$l$ d$ coca% ,in acid cinamic s$ poat$ ob!in$ acidl &$nilpropiolic%
Acid+l c#i'a"te1ic a &ost id$nti&icat (n &loril$ d$ pir$tr% Kl a &ost ob!int i prin sint$z+ "*$zi sint$z$ d$ acizi
n$satra!i#% Acidl i $st$rii pr$zint+ propri$t+!i ins$cticid$%
Acizii nesaturai sueriori) pr$zint+ n int$r$s d$os$bitM $i intr+ (n constit!ia 'r+similor%
Acidul almitoleic) cis1H1-$xad$c$noic "C541H) nd$ r$pr$zint+ pozi!ia dbl$i sa dbl$lor l$'atri#)
$st$ pr$z$nt (n l$iri *$'$tal$ i (n c$rri% P7n+ la 26P s$ '+s$t$ (n l$i d$ p$t$
Acidul oleic) cis1H%1octad$c$noic) $st$ c$l mai r+sp7ndit acid (n r$'nl *$'$tal%
Kst$ principala compon$nt+ a l$ili d$ m+slin$) d$ &loar$a soar$li i a altor 'r+simi nd$ s$ '+s$t$ ca $st$r
al 'lic$rin$i% Strctra acidli ol$ic a &ost stabilit+ prin -idro'$nar$ (n acid st$aric) apoi prin ozonoliz+ i
d$scompn$r$a ozonid$i (n ald$-id$%"ald$-id$l$ s$ trans&orm+ prin oxidar$ (n acizii cor$spnz+tori sa prin
sint$z$#% Acidl ol$ic "C5G) H sa cis1H1octad$c$noic# $st$ lic-id incolor) inodor% Acidl $laidic $st$ solid i n
s$ '+s$t$ (n natr+% Acidl ol$ic $st$ sol*$nt p$ntr n$l$ *itamin$ i m$dicam$nt$%
Acidul etroselic "C5G) 4M cis141Octad$c$noic# a &ost ps (n $*id$n!+ (n l$i d$ p+trnI$l $tc%
8
2
C "C8
2
#
F
COO8
8
2
C "C8
2
#
F
C8
3
8
2
; cat%
C "C8
2
#
F
COO8
C "C8
2
#
F
C8
3 O
3
Ozonida
COO8 "C8
2
#
F
8
8 C "C8
2
#
F
C8
3
O O
O
C
O8C "C8
2
#
F
COO8
Monoald$-ida ac$laicV
Ald$-ida p$lar'onicV
C8
3
"C8
2
#
F
C8O
8
2
O
acid ol$ic"cis1H1octad$c$noic#
acid st$aric
8 COO8
8 C
C8
3
C8
3
C
8
C8
3
C8
3
)
9
- "C
54
C8
3
"C8
2
#
9
C C
8
8
"C8
2
#
F
COO8
acid crizant$mic
acid palmitol$ic
Acid truxilic
Acid truxinic
C
6
H
5
CH CH COOH 2
C
6
H
5
CH CH COOH
COOH CH CH C
6
H
5
HOOC
C
6
H
5
CH CH COOH
CH CH C
6
H
5
133 T.t.
T.t.
C
o
(acid hidrocinamic)
fenilroionic
cinamic Acid
Acid
C
6
H
5
CH
2
CH
2
COOH
H
2
/$at
C
6
H
5
CH
HC COOH
o
C
57
Acid alocinamic
C
6
H
5
CH
CH
HOOC
+COOH
COOH
CH
3
COOH
6 5
O
HC COOH
CH CH
3
H
2
/ $at
CH
3
CH
2
CH
2
COOH
Acidul vaccenic "C5G) 55M trans1551Octad$c$noic# $st$ sin'rl acid sp$rior car$ s$ '+s$t$ ca izom$r trans
(n 'r+simi animal$%Acidul sterculic "C5H) H ciclic# a &ost izolat din 'r+sim$a plant$i +terculia foetida Con!in$
5H atomi d$ carbon i n cicl d$ tr$i atomi%
Acid+l c=a+l1oo3#ic Bi acid+l =Fd"oca#(ic a &ost izola!i din &rct$l$ nor arbori tropicali% Kst$rii lor a &ost
tiliza!i mlt timp la combat$r$a l$pr$i%
Acidul gadoleic "C26) H#) cis1H1$icosa$noic $st$ r+sp7ndit (n 'r+simil$ animal$lor d$ mar$%
Acidul erucic "C22) 53#) cis1531docosa$noic s$ '+s$t$ ca izom$r cis (n l$il d$ rapi!+ i mtar% Izom$trl
trans) acidl brasidic n s$ '+s$t$ (n natr+% Ki &orm$az+ o p$r$c-$ d$ izom$ri '$om$trici%
Acidul micolienic) C2F) 2 0 rami&icat) a &ost izolat din bacilii tb$rcloz$i nd$ s$ '+s$t$ sb &orm+ d$
$st$ri ai za-arrilor%
In n$l$ l$iri) acizii n$satra!i snt (nso!i!i d$ -idroxiacizi n$satra!i%
Acidul ricinoleic $st$ $xtras din l$i d$ ricin% La t$mp$ratr+) $l s$ d$scompn$ (n acidl nd$cil$nic
important (n par&m$ri$ i &armaci$ i -$ptanal%
Aci'i (oli"e&at+#a!i 1o"oca#o$ilici
Acizii polin$satra!i monocarboxilici snt compi natrali sa d$ sint$z+ i pr$zint+ n sist$m d$ dbl$
l$'+tri conI'at$ sa l$'+tri dbl$ izolat$
Acid+l &o#ic) 2)>)1-$xadi$n1carboxilic) a &ost izolat din &rct$l$ scorli d$ mnt$ i din alt$ plant$
s7mbroas$ "Sorbs#% Sint$tic s$ pr$par+ prin cond$nsar$a ald$-id$i crotonic$ c acid malonic (n pr$z$n!a
piridin$i) sa &olosind $st$r malonic% Acidl sorbic $st$ solid i ar$ L%t% 53>oC% Kst$ n$toxic% Ar$ ac!in$
s$l$cti*+ aspra droIdiilor i mc$'airilor% In conc$ntra!ii 6)516)2P ar$ propri$t+!i cons$r*ant$ i stabilizant$
p$ntr n$l$ prods$ "*in) br7nz+) sta&id$#%
$etanal
Acid undecilenic
Acid ricinoleic
C8
2
C8 "C8
2
#
G
COO8 + C8
3
"C8
2
#
9
C8O
o
t
C8
3
"C8
2
#
9
C8"O8# C8
2
C8 C8 "C8
2
#
F
COO8
8C
8C
"C8
2
#
F
"C8
2
#
55
C8
3
COO8
C8
3
"C8
2
#
F
C8
8C "C8
2
#
55
COO8
"R%Robinson#
C8
3
"C8
2
#
5F
C8 C8
2
C8 C8 C COO8
C8
3
C8
3
C8
3
acid $rcic1cis acid brasidic1trans "L%t%:3>
o
C# "L%t%:46
o
C#
acid micolip$nic
8C C8
8
2
C C8
2
C
8
"C8
2
#
52
COO8
8C
C8
2
C8
2
C8
C
8
"C8
2
#
56
COO8
C8
3
"C8
2
#
H
C
COO8 "C8
2
#
F
C
8
8
acid c-almoo'ric
acid -?dnocarpic
acid 'adol$ic
acid st$rclic
acid *acc$nic
acid p$tros$lic
COO8 "C8
2
#
F
C8
2
C C "C8
2
#
9
C8
3
C8
3
"C8
2
#
9
C
COO8 "C8
2
#
H
C
8
8
C8
3
"C8
2
#
56
C
COO8 "C8
2
#
>
C
8
8
Qolosind m$toda d$ sint$z+ dat+ mai ss) a &ost ob!in!i acizi poli$nici d$ &orma:
C831"C8:C8#n1COO8) (n car$ n : 31G% C7nd n >3) acizii poli$nici snt colora!i% Pornind d$ la acizii poli$nici
s1a r$alizat sint$z$ d$ acizi 'rai sp$riori%
I" 3#,&i1i) a &ost id$nti&ica!i i izola!i acizi sp$riori c mai mlt$ dbl$ l$'+tri din car$ nii a &ost
sint$tiza!i%
Acid+l li"olic) "C5G H)52#) cis) cis 0 H)52 0 octad$cadi$noic) s$ '+s$t$ (n 'r+simi% Pr$zint+ izom$ri
'$om$trici% Strctra a &ost d$monstrat+ prin d$'radar$ oxidati*+ i prin sint$z+% Acid+l li"ole"ic) "C5G)
H)52)59#) cis) cis) cis1H)52)591octod$catri$noic) $st$ pr$z$nt (n l$iri sicati*$) d$ in sa rapi!+% Strctra a &ost
stabilit+ prin ozonoliz+ i prin sint$z+ c7nd s1a pr$cizat i con&i'ra!ia cis1cis1cis%A*7nd mai mlt$ l$'+tri
dbl$ s$ oxid$az+ i s$ polim$riz$az+%
Acid+l elaeo&tea#ic) "C5G H)55)53#) sa 1H)55) 531octad$catri$noic) apar$ (n l$i d$ tn' "C-ina# i alt$
'r+simi *$'$tal$% Pr$zint+ o &orm+ labil+ trans1trans1cis c L%t% >GoC "(n l$i d$ tn'#) car$ sb in&l$n!a
lminii sa a c+ldrii i a catalizatorilor tr$c$ (n &orma 1stabil+ trans1trans1trans c L%t% F5oC%
Acid+l a#a=ido"ic) "C26) 9)G)55)5>#) acid 9)G)55)5>1$icosat$tra$noic) $st$ pr$crsor al prosta'landin$lor% S$
'+s$t$ (n cr$i$r i s7n'$ (n cantitat$ mic+%
Acid+l cl+(a"odo"ic) "C22) >)G)52)59)5H#) acid >)G)52)59)5H1docosap$nta$no$ic) s$ '+s$t$ (n l$i d$ p$t$ i
animal$ marin$% Kst$ n acid instabil "s$ izom$riz$az+ r$p$d$#% Strctra dbl$lor l$'+tri izolat$ s$ d$t$rmin+
prin d$'radar$ oxidati*+%
Acid+l doco&a=e$ae"oic) "C22) 9)G)55)5>)5F)26#) a &ost d$ as$m$n$a ps (n $*id$n!+ (n n$l$ 'r+simi% In
n$l$ 'r+simi a &ost id$nti&icat i n cetoacid (oli"e&at+#at(acid+l lica"ic) acid H)55)531>1c$to1
octad$catri$noic#%
Aci'i "e&at+#a!i dica#o$ilici Bi t#ica#o$ilici
Acid+l 1aleic $st$ n comps ob!int indstrial prin oxidar$a b$nz$nli) (n &aza 'azoas+) c a$r (n
pr$z$n!+ d$ *anadi c7nd s$ izol$az+ sb &orm+ d$ an-idrid+: C>82O3%
Kst$ solbil (n ap+% Qnc!ion$az+ ca acid tar$% < s$ '+s$t$ (n natr+% Ar$ tiliz+ri (n ob!in$r$a r+inilor
sint$tic$ i a altor prodi) &iind o mat$ri$ prim+ i$&tin+%
Acid+l D+1a#ic s$ '+s$t$ (n natr+) dar poat$ &i ob!int i prin sint$z+% In c$ll$l$ *ii) acidl &maric
$st$ int$rm$diar (n m$tabolisml -idra!ilor d$ carbon% A &ost id$nti&icat (n Qmaria o&&icinalis) (n lic-$ni i
cip$rci% Prin sint$z+ s$ ob!in$ din acidl 1-idroxisccinic "acid malic# prin (nc+lzir$ la 5>61596oC) sa din
acidl bromsccinic prin $liminar$a acidli brom-idric Acidl &maric $st$ 'r$ solbil (n ap+% Kst$ acid mai
slab "=i: H)9%561># d$c7t acidl mal$ic "=a: 5>2%561>#% P$st$ 266oC sblim$az+%
,a #idrogenare) at7t acidl mal$ic 0cis c7t i acidl &maric 0trans tr$c (n acid sccinic% R$zlt+ c+ snt
izom$tri '$om$trici%
acidl $la$ost$aric "L%t%:>G
o
C#
(CH
2
)
7
COOH CH
3
(CH
2
)
3
CH CH CH CH CH CH
acidl licanic
COOH
CH
3
G
20
14 11
5
1
acid ara-idonic
(CH
2
)
4
C
O
CH
2
CH
2
COOH (CH
2
)
3
CH
3
(CH CH)
3
"C8
2
#
F
COO8
C8
3
"C8
2
#
>
CH CH CH
2
CH CH "C8
2
#
F
COO8
C8
2
C8
3
CH CH CH
2
CH CH C8
2
CH CH
cis cis cis
acidl linolic "L%t%:19
o
C#
acidl linol$nic "L%t%:155
o
C#
-
-
C8
3
C8 C8 C8 C8 COO8
CO
2
8
2
O
P?
+ 8
2
C"COO8#
2
C8
3
C8 C8 C8O
Acid+l 1+co"ic s$ &orm$az+ prin oxidar$a b$nz$nli) &$nolli sa pirocat$-in$i c p$racizi% In natr+ s$
'+s$t$ $st$ri&icat% Acidl mconic pr$zint+ izom$ri$ cis1trans% S$ cnosc tr$i izom$ri: cis1cis1 L%t% 5GFoC) cis1
trans1 L%t% 5G>oC) trans1trans1L%t% 366oC%
Acid+l aco"itic r$zlt+ din trans&orm+ril$ acidli citric% Acidl aconitic $st$ n antioxidant i n stabilizant al
arom$lor *olatil$ "*% pr+Iir$a ca&$l$i#%
Aci'i "e&at+#a!i c+ t#i(le le3,t+#i
Acizii din ac$ast+ 'rp+ snt (n '$n$ral compi d$ sint$z+ i mai rar pr$z$n!i (n natr+%
Acid+l (#o(iolic ar$ strctra: 8CC1COO8% S$ ob!in$ prin sint$z+ din ac$til$n+ prin m$toda
carboxil+rii sa prin d$carboxilar$a par!ial+ a acidli ac$til$ncarboxilic%
Acidl propiolic $st$ n comps incolor) L%t% 5GoC i L%& 5>>oC% Ar$ miros acc$ntat d$ acid ac$tic%
Polim$riz$az+ or tr$c7nd (n acid trim$sic%
Acid+l De"il(#o(iolic s$ ob!in$ din acidl cinamic prin adi!i$ d$ brom rmat+ d$ $liminar$a -idracidli:
In natr+ s$ '+s$t$ n acid sp$rior monocarboxilic c o tripl+ l$'+tr+ (n mol$cl+) acidul tariric%
Acid+l ta#i#ic) "C5G) 4#) a &ost izolat din l$il $xtras din s$min!$l$ d$ Picramnia tariri "SWrr$ns$n#%
C
6
H
5
CH<- CH<- COOH
H<-
-
2
C
6
H
5
C C COOH
C
6
H
5
CH CH COOH <-
2
+ C
6
H
5
CH<- CH<- COOH
o
HC C= #a
+
+ CO
2
HC C COO#a
H
+
HC C COOH
sau
HOOC C C COO:
t
HC C COO: CO
2
+
C
CH
COOH CH
2
COOH C
COOH
- H
2
O
175
CH
2
COOH
CH
2
COOH
C
COOH
OH
o
COOH
COOH RCO
3
H
OH
OH
,
,
OH
acid mconic
8
2
;cat%
acid sccinic
CH
2
HOOC
CH
2
HOOC
acid mal$ic
H C COOH
C COOH H
C
A$!% ?u'a-!$
- H<-
<- CH
HOOC
CH
2
HOOC
HOOC C H
C COOH H
OH
CH
HOOC
CH
2
HOOC
140 150
o
L%t%2G4
o
C "capilar inc-is#
Acid+l de 1at#ica#ia a &ost izolat sb &orm+ d$ $st$r m$tilic din l$i d$ &lori d$ m$!$l% Kl con!in$ p$ l7n'+
tripla l$'+tr+ i do+ l$'+tri cis) cis) dbl$
Acid+l acetile"-dica#o$ilic s$ ob!in$ din acidl &maric prin bromrar$ rmat+ d$ d$-idro-alo'$nar$:
Kst$rii acidli ac$til$n dicarboxilic particip+ la r$ac!ii d$ cicloadi!i$
HOOC CH CH COOH
<-
2
HOOC CH<- CH<- COOH
H<- 2 -
HOOC C C COOH
CH
3
CH CH C C CH CH COOCH
3
2
CH
3
(CH
2
)
10
C C (CH
2
)
4
COOH