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Composf| corbon|||c|

Cue:Ii ccmpc:Ii :cnc ccrcIIerizzcIi cc||c pre:enzc ce| gruppc C/F8CNlLE:


R R'
O

l| ccrLcnic ce| gruppc C=C |egcIc cc enIrcmLi i |cIi cc cIcmi uguc|menIe c
menc e|eIIrcnegcIivi, c::ic C cppure H.
Ccrri:pcnccnc cc unc :IcIc ci c::icczicne :upericre ci 2 cg|i c|ccc|i
ccrri:pcncenIi. Ne| cc:c ce||e c|ceici, infcIIi, i| C hc numerc ci c::icczicne + 1,
menIre neg|i c|ccc|i primcri i| C che pcrIc |CH hc numerc ci c::icczicne - 1. Ne|
cc:c cei cheIcni, invece, i| C hc numerc ci c::icczicne + 2, ec zerc neg|i c|ccc|i
:eccnccri.

Nomenc|ofuro
Fer |e c|ceici |c ce:inenzc -/LE:
O
H
H
O
CH
3
-CHO

ln figurc :cnc rcppre:enIcIe i| 2-meIi|LuIcnc|e, |eIcnc|e {ncme cu:c
cceIc|ceice) e |c Lenzc|ceice. l| primc Iermine ce||c :erie, HCHC, in cui |unicc
cIcmc C ue||c ce| ccrLcni|e, :i chicmc FCFM/LDElDE.
Fer i cheIcni :i puc ccre i| ncme c||inIerc ccIenc e :pecificcre ccve :i Ircvc i|
ccppic |egcme, cppure ccre i| ncme c||e cue ccIene ci cue |cIi ce| gruppc
ccrLcni|e. Lc ce:inenzc per i cheIcni -CNE.
O
O
O
O

ln figurc :cnc mc:IrcIi i| primc Iermine ce||c :erie, i| cui ncme cu:c /CEICNE,
menIre i| ncme :i:IemcIicc FFCF/NCNE c cimeIi|cheIcne: i| 3-epIcncne {c eIi|-
LuIi|cheIcne): i| 2-LuIcncne c meIi|eIi|cheIcne: |cceIcfencne.
F = c|chi|e CHEICNl
F = H /LDElDl

Fropr|efo f|s|che
l ccmpc:Ii ccrLcni|ici :cnc ccrcIIerizzcIi cc||c pre:enzc ci un fcrIe mcmenIc
cipc|cre rivc|Ic ver:c |c::igenc, i| che, cnche in c::enzc ci |egcme icrcgenc,
rence i Iermini pi piccc|i ccmp|eIcmenIe mi:ciLi|i ccn |ccuc.




Fer ccnfrcnIc, i| mcmenIc cipc|cre ce||eIcnc|c ci 1, D, ue||c ce||eIere
cieIi|icc ci 1,30 D. Cue:Ic :ignificc che |c I ci eLc||izicne :crc re|cIivcmenIe c|Ic
{ncn ucnIc i ccmpc:Ii ccn |egcme icrcgenc). Lc fcrmc|ceice {HCHC, |c pi
piccc|c ce||e c|ceici), pur ncn cvencc |egcme icrcgenc perch ne::un H
|egcIc c C, mc :cnc enIrcmLi |egcIi c C, ccmp|eIcmenIe mi:ciLi|e ccn |ccuc
per vic ci ue:Ic c|Ic mcmenIc cipc|cre, e |c :Ie::c vc|e per |cceIcne.
ALDEIDI solub. H
2
O T
EB
(C)
HCHO completa - 21
CH
3
CHO completa + 20
C
2
H
5
CHO 16 g/100 g + 49
C
3
H
7
CHO 7 g/100 g + 76
PhCHO scarsa + 178

keoff|v|fo de| composf| corbon|||c|
H H
O



Le c|ceici, grczie c||c pre:enzc ce||icrcgenc :u| ccrLcni|e, :i c::iccnc mc|Ic pi
fcci|menIe cei cheIcni. Lc:cicIe c||cric Ienccnc c :uLire cuIc::icczicne
Irc:fcrmcncc:i nei ccrri:pcncenIi ccici ccrLc::i|ici {veci).
H H
O

D
= 2,27 D
C H
3
H
O

D
= 2,75 D
C H
3
CH
3
O

D
= 2,85 D
C H
3
CH
3
O

D
= 2,85 D

CHETONI solub. H
2
O T
EB
(C)
acetone completa 56
2-butanone 26 g / 100 g 80
3-pentanone 5 g / 100 g 101
3-esanone scarsa 124
acetofenone scarsa 218

C
+
- cIIcccc nuc|ecfi|c
Lc:iciIc - cIIcccc e|eIIrcfi|c
:Ircppc ci H - c::icczicne
enc|izzczicne
H H
O O
O
OO
.
.
O
2
Fer c::iccre un cheIcne ccccrre
invece rcmpere un |egcme C-C, i| che mc|Ic pi ciffici|e e richiece ccncizicni
pi crc:Iiche.
Lc reczicne ccrcIIeri:Iicc ce| gruppc ccrLcni|e, :ic per c|ceici che per cheIcni,
|ADDIIIONE NbCLEOFILA, cerivcnIe cc| fcIIc che in ue:Ic gruppc c unc fcrIe
pc|crizzczicne ccn unc ccricc pcrzic|e pc:iIivc :u| ccrLcnic, in grccc ci cIIircre un
nuc|ecfi|c pc|cre c ccricc:

Fer |e c|ceici |c reczicne pi ve|cce che per i cheIcni, :ic per mcIivi ci mincr
ingcmLrc inIcrnc c| cenIrc ce||c reczicne, :ic perch |c ccricc + :u| ccrLcnic pi
fcrIe {:i riccrci che i gruppi c|chi|ici re:pingcnc g|i e|eIIrcni).
l| primc pc::cggic uinci |c fcrmczicne {e:cIermicc) ci un nucvc |egcme Irc i|
C ce| ccrLcni|e e i| nuc|ecfi|c, ccn rcIIurc ce| |egcme C-C: g|i e|eIIrcni :i
:pc:Icnc :u||C, che civenIc cc:| :ece ci ccricc negcIivc. / ue:Ic punIc C
-

prence un H
+
cc||ccuc e |c reczicne :i ccmp|eIc. Si IrcIIc ci unc :cmmc c
ccppic |egcme :imi|e c ue||c vi:Ic per g|i c|cheni, mc ui i| |egcme :u cui
cvviene |c :cmmc pc|cre e ue:Ic cirige |c fcrmczicne cei nucvi |egcmi.
l| nuc|ecfi|c che cIIcccc puc e::ere un cnicne, ccme CH
-
cppureCN
-
, cppure puc
e::ere unc mc|ecc|c neuIrc ccn cei ccppieIIi ci:pcniLi|i, ccme |ccuc c un
c|ccc|. ln ue:Iu|Iimc cc:c :i fcrmcnc :c:Icnze chicmcIe em|oceto|| c oceto||, c
:eccncc che recgi:ccnc ccn unc c ccn cue mc|ecc|e ci c|ccc|:
O
Nu
O
Nu
OH
:Nu
H
2
O

Lc reczicne in cgni cc:c pi fcci|e e ve|cce ne| cc:c ce||e c|ceici, ccve
richiece :c|c unc ccIc|i:i ccicc. Lingre::c ci unc mc|ecc|c ci c|ccc| cc |ucgc
c||emicceIc|e. ln :eguiIc, per prcIcnczicne, |CH rimc:Ic :e ne vc c prcpric vc|Ic
e viene :c:IiIuiIc cc unc :eccncc mc|ecc|c ci c|ccc|.

C H
3
H
OH
OMe
C H
3
H
OMe
OMe
C H
3
H
OH
2
OMe
CH
3
OH
H
+

{i| gruppc inciccIc ccn Me meIi|e). /nc|cgc c ue:Ic |c reczicne ci
icrcIczicne ce||e c|ceici, che pcrIc c||c fcrmc icrcIc:
C H
3
H
O
C H
3
H
O H
OH
H
2
O / H
3
O
+

Cuinci un cic|c cc:icceIIc geminc|e", cic ccn cue CH :u||c :Ie::c ccrLcnic,
ncn c|Irc che |c fcrmc icrcIc ci un ccmpc:Ic ccrLcni|icc, che hc :cmmcIc
ccuc c| ccppic |egcme C=C. Lc fcrmc icrcIc ci :c|iIc menc :IcLi|e ce|
ccrLcni|e, e puc e:i:Iere :c|c in piccc|c percenIuc|e c||eui|iLric, Ircnne c|cuni
cc:i pcrIicc|cri. G|i emicceIc|i e g|i cceIc|i :i pc::cnc invece cIIenere in fcrmc
:IcLi|e. Ccn cheIcni |c reczicne cLLc:Icnzc :fcvcriIc: :i puc cIIenere cpercncc
in c|ccc| ccme :c|venIe e rimucvencc |ccuc che :i fcrmc cc||c ccncen:czicne
mecicnIe ci:Ii||czicne czecIrcpicc. Lc reczicne in IuIIi i cc:i s|ovorevo|e do|
punto d| v|sto entrop|co {ciminuzicne ci mc|i), mc per |e c|ceici mc|Ic pi
e:cIermicc: H {kJ mc|
-1
) vc|e -7,5 per HCHC, -3, per CH
3
CHC e -4 per
|cceIcneLc fcrmczicne ci emicceIc|i e ci cceIc|i :crc impcrIcnIe ne||c :IruIIurc
C H
3
H
O
C H
3
CH
3
O
C H
3
H
OH
O
CH
3
C H
3
CH
3
OH
O CH
3
C H
3
H
OMe
OMe
C H
3
CH
3
OMe
OMe
+ CH
3
OH
+ CH
3
OH
Me = CH
3
ceg|i zuccheri, che :cnc ccmpc:Ii |c cui mc|ecc|c ccnIiene :ic gruppi CH che
ccrLcni|e, i uc|i pc::cnc ccncen:cre frc |crc c||inIernc ce||c :Ie::c mc|ecc|c.
Un c|Irc Iipc ci nuc|ecfi|c che puc enIrcre :u| ccrLcnic ci un ccrLcni|e |czcIc
ce||cmmcniccc c ci uncmminc: :i puc cc:| fcrmcre unlMMlN/, ceIIc cnche
cc:e c| Scn|||.

Ccme :i vece, in ue:Ic cc:c |c mc|ecc|c fcrmcIc c||inizic Ience cc e|imincre
ccuc rifcrmcncc i| ccppic |egcme, cc:| che c| Iermine i| |egcme C=C :i
Irc:fcrmcIc in un |egcme C=N.
Ne| cc:c ci cheIcni e cmmine, |c genericc reczicne civenIc:

l| ccppic |egcme hc |c pc::iLi|iIc ci e::ere ci: c Ircn:.
Unc pcrIicc|cre mccc|iIc ci reczicne cei ccmpc:Ii ccrLcni|ici ccinvc|ge i|
ccrLcnic cciccenIe, ucncc :ic |egcIc cc c|menc un cIcmc H, cIIrcver:c un
eui|iLric chicmcIc IAbIOMEkIA CHEIOENOLICA:
Si IrcIIc ci un eui|iLric frc cue mc|ecc|e civer:e, in ucnIc c un cIcmc H |egcIc
ccn |egcme in un cc:c c| C cciccenIe, ne||c|Irc c||C ce| ccrLcni|e. Lc rcIIurc
ci un |egcme e uinci i| ccmLicmenIc ce||c ccnccIenczicne ceg|i cIcmi unc
verc e prcpric reczicne chimicc {ncn :i IrcIIc uinci ci :emp|ice ce|ccc|izzczicne
ci e|eIIrcni, |e cue :IruIIure ci:egncIe ncn :cnc in ri:cncnzc frc |crc mc e:i:Icnc
effeIIivcmenIe in eui|iLric frc |crc, cic:cunc per unc ccIc 7 ce||c mi:ce|c IcIc|e).
Ncrmc|menIe |c fcrmc cheIcnicc pre:enIe in mcggicr ucnIiIc perch pi
:IcLi|e {|egcmi in IcIc|e pi fcrIi): unimpcrIcnIe eccezicne rcppre:enIcIc cci
R H
O
R H
OH
NH
2
R H
NH
NH
3
+ H
2
O
R R'
O
R R'
OH
NH
X
R R'
N
X
X NH
2
+ H
2
O
O
H
OH
FENCLl, che :cnc g|i c|ccc|i crcmcIici. Se infcIIi |c fcrmc enc|icc ci un ncrmc|e
ccmpc:Ic ccrLcni|icc {en-c|c un c|ccc| in cui i| gruppc CH vini|icc, cic
cireIIcmenIe |egcIc c un C che fc pcrIe ci un ccppic |egcme) menc :IcLi|e
ce||c fcrmc cheIcnicc, ucncc i| ccppic |egcme fc pcrIe ci un :i:Iemc crcmcIicc
|c :uc rcIIurc ccu:c perciIc ci :IcLi|izzczicne crcmcIicc e uinci ncn fcvcriIc.
OH
O
H H
CH
2
OH O

Se |c IcuIcmeric cheIcenc|icc un eui|iLric chimicc che ccn:i:Ie ne||c
:pc:IcmenIc ci un cIcmc H, :e ue:Ic H viene per:c {hc unc cerIc cciciIc e puc
venir :IrcppcIc cc Lc:i cLLc:Icnzc fcrIi) |cnicne ENCL/IC che ne ri:u|Ic un
cnicne ce|ccc|izzcIc, in cui |c ccricc :i puc :iIucre in cue pc:izicni ncn euivc|enIi:

Si IrcIIc percic ci un cnicne 8lDENI/IC, che :e recgi:ce ccn unc :pecie e|eIIrcfi|c
puc :uLire |cIIcccc in cue pc:izicni civer:e, ccncc |ucgc c cue prcccIIi civer:i.
ln pcrIicc|cre, |cIIcccc ci un X
+
:u c::igenc :pe::c mc|Ic pi rever:iLi|e {X
+
Icrnc
c :Iccccr:i mc|Ic pi fcci|menIe) ri:peIIc c||cIIcccc ce||c :Ie::c :pecie :u| C.
Spe::c uinci |c recIIiviIc cei ccmpc:Ii ccrLcni|ici ccmpcrIc |c pc::iLi|iIc ci
cIIcccc nuc|ecfi|c :u||c fcrmc enc|icc, cvverc :u| C ce|||cnicne enc|cIc. l cheIcni,
cc e:empic, pc::cnc e::ere LrcmurcIi ne||c pc:izicne cciccenIe c| ccrLcni|e in
mccc cLLc:Icnzc fcci|e:

H = - 58, kJ mc|
-1

H = + 7,0 kJ mc|
-1

O
O
O
O
OH
O
O
Br
base
Br
2
+ Br
-
Lc ccIc|i:i Lc:icc :erve per |c fcrmczicne inIermecic ce||cnicne enc|cIc, che pci
recgi:ce ve|ccemenIe ccme in uncccizicne e|eIIrcfi|c cc c|chene, fcci|iIcIc cc|
ccnIriLuIc ce||cnicne:
Lc principc|e reczicne che ccinvc|ge |c IcuIcmeric cheIcenc|icc |c
CCNDENS/ZlCNE /LDCLlC/, in cui cue mc|ecc|e ce| ccmpc:Ic ccrLcni|icc i
uni:ccnc c fcrmcre unicrc::ic|ceice c icrc::icheIcne:


Ccme :i vece, unc ce||e cue mc|ecc|e ccrLcni|iche perce H
+
fcrmcncc |cnicne
enc|cIc, i| uc|e cIIcccc i| C pc:iIivc ce||c|Irc mc|ecc|c fcrmcncc un nucvc
|egcme C-C. l| ccrLcni|e ce||c mc|ecc|c che civenIc cnicne rimcne ccrLcni|e,
menIre ue||c che :uLi:ce |cIIcccc civenIc CH. /||c fine, |icrc::icheIcne puc
ccre e|iminczicne ci ccuc fcrmcncc i| ccppic |egcme in pc:izicne ccniugcIc c|
ccrLcni|e {= :IcLi|izzcIc per ri:cncnzc). Ficcrcicmc che ccniugcIc :ignificc che frc
i cue ccppi |egcmi ncn ci :cnc C iLricizzcIi :p
3
, mc g|i e|eIIrcni cc:IiIui:ccnc un
:i:Iemc ce|ccc|izzcIc ccnIinuc.
/nche i fenc|i hcnnc ue:Ic Iipc ci recIIiviIc: per ue:Ic :cnc pi ccici ceg|i
c|ccc|i c|ifcIici, ccIc che |cnicne ri:u|IcnIe :IcLi|izzcIc per ri:cncnzc:



O
Br-Br
R
O
O
R
O
R
R
OH
R
O
O
R
R
OH
-
O O
O
O



MenIre g|i c|ccc|i c|ifcIici hcnnc cciciIc infericre c ue||c ce||ccuc, i| pKc ce|
fenc|c ci circc 10. l| fencIc, ccme i| fenc|c, fcrIemenIe cIIivcIc ver:c |c
:c:IiIuzicne e|eIIrcfi|c crcmcIicc.
Ccn Lrcmc, i fenc|i recgi:ccnc ccme i cheIcni, cIIrcver:c |c fcrmc enc|icc:

l| fenc|c cc:| cIIivcIc che |c Lrcmurczicne vc c :cIurcre IuIIe |e pc:izicni crIc e
pcrc ci:pcniLi|i {ue||e ccve :i |ccc|izzc |c ccricc ce||c icne fencIc). Si ceIIc che
|c fcrmc enc|icc unc piccc|c pcrIe ce||c mi:ce|c c||eui|iLric, mc ue||c che
recgencc fcrmc i prcccIIi in mcnierc irrever:iLi|e: mcn mcnc che recgi:ce, uinci,
c|Irc :e ne fcrmc, finc c e:curire i| recgenIe {:pc:IcmenIc ce||eui|iLric per |egge
ci czicne ci mc::c).l| fenc|c puc ccre cnche ccncen:czicne ccn c|ceici:
O
O
O
OH
OH
OH

Lc reczicne ce| IuIIc cnc|cgc c||c ccncen:czicne c|cc|icc, Ircnne che i|
ccrLcni|e che :uLi:ce |cIIcccc ue||c ce||c|ceice, menIre i| ccrLcni|e ce||c
fcrmc enc|icc ce| fenc|c c||c fine Icrnc c||c fcrmc enc|icc crcmcIicc.
Lc reczicne Irc fenc|c e fcrmc|ceice frc |e prime :inIe:i ci pc|imeri mci :IucicIe: i|
pc|imerc che cc:| :i fcrmc reIicc|cIc, perch i| fenc|c hc 3 pc:izicni recIIive, e
uinci IermcincurenIe e rigicc, ncn ricic|cLi|e.





O
OH
Br
Br Br





Si IrcIIc ci unc re:inc chicmcIc 8/KELlIE, u:cIc ccme pc|vere cc :Icmpcggic per
Ie|efcni, cru:ccIIi, invc|ucri ci cppcrecchi e|eIIrici ecc.
Lc icne fencIc puc cIIccccre mc|ecc|e pc|crizzcIe c ccn ccricc pc:iIivc:
O
OH
HOOC
OH
CHO
N
N
OH
+ CO
2
+ CHCl
3
+ Ar-N
2
+

Si ncIi che, cIIccccncc i| c|crcfcrmic {un cIcmc ci C| viene :c:IiIuiIc cc| fencIc) :i
cIIiene un cic|crcmeIi|-fenc|c che, per icrc|i:i, cc |c|ceice.
OH Cl
Cl
H
OH Cl
OH
H
OH OH
OH
H
OH
CHO

l cifenc|i ccnnc |ucgc cc un eui|iLric reccx ccn |c fcrmc c::iccIc ceIIc
CHlNCNE. Si IrcIIc ci un cic|ce:cciencne.





/ :ini:Irc, |eui|iLric Irc 1,2-cifenc|c {crIc-icrcchincne) e |crIc-Lenzcchincne: c
ce:Irc, |eui|iLric Irc pcrc-icrcchincne e pcrc-Lenzcchincne. /|Iri chincni ci
impcrIcnzc incu:Iric|e :cnc:
-
CH

O
O
OH
OH
ox
red
O
O
OH
OH
ox
red
ccIc|i:i
Lc:icc

ccncen:czicne

reIicc|czicne
O
O
O
O



Lc reczicne reccx :i puc :chemcIizzcre ccme :egue:

l| pcIenzic|e ccIc cc:

ccve i vc|cri ci E per i vcri ccmpc:Ii :cnc i :eguenIi {pi c|Ic i| pcIenzic|e ci
ricuzicne, pi :IcLi|e |c fcrmc riccIIc).
ch|none E [V} ch|none E [V}
1,4-8enzcchincne 0, 1,2-NcfIcchincne 0,5
1,2- 8enzcchincne 0,78 1,4-NcfIcchincne 0,47
2-CH-1,4- 8enzcchincne 0,5 ,10-/nIrcchincne 0,13

l| :i:Iemc reccx rever:iLi|e chincne-icrcchincne mc|Ic ciffu:c in ncIurc e funzicnc
:pe::c cc cnIic::iccnIe ncIurc|e c||inIernc ce||e ce||u|e.
E cnche c||c Lc:e ce||c :IruIIurc cei cc|crcnIi cnIrcchincnici, unc ccIegcric ci
cc|crcnIi che ccmprence uc:i IuIIe |e c|c::i IinIcric|i, ccIc che :u| :i:Iemc
ce||cnIrcchincne :i pc::cnc i:Irccurre gruppi :c:IiIuenIi ci vcric pc|criIc e
recIIiviIc.
1,4-ncfIcchincne ,10-cnIrcchincne
OH
OH
O
O
+ 2 H
+
+ 2 e
E = E- log
0,059
n
[idrochinone]
[chinone]
= E
+ 0,0295 log
[idrochinone]
[chinone]
O
O
O
O
Al
O
O
O
O
Ca
2+

Lc grcnce impcrIcnzc cei cc|crcnIi ccrLcni|ici cipence cc cue fcIIcri:
1} |c fcci|iIc ccn cui i cue ccrLcni|i pc::cnc e::ere riccIIi c cifenc|i :c|uLi|i in ccuc
2} Si hcnnc Lcnce ci c::crLimenIc cc c|Ie |unghezze c'cncc cnche ccn piccc|i
:i:Iemi ccniugcIi. Fercic ccn :c:IiIuzicni re|cIivcmenIe :emp|ici :i cIIengcnc
ccmpc:Ii che c::crLcnc ne| ccmpc ce:icercIc ce||c :peIIrc finc c| vicinc
infrcrc::c.







An|||ne
Fer finire, un cennc c||e cmmine crcmcIiche. Fi:peIIc c ue||e c|ifcIiche :cnc
menc Lc:iche, :empre perch i| ccppieIIc ce||czcIc, ccme ue||i ce||c::igenc
nei fenc|i, puc e::ere cecuIc ver:c |cne||c, ccncc |ucgc c unc :erie ci fcrme ci
ri:cncnzc ccn unc ccricc negcIivc ce|ccc|izzcIc ne||e pc:izicni crIc e pcrc:





Fc::c Iurcc
O
O
OH
OH

Gic||c /|izcrinc
NH
2
NH
2
+
NH
2
+
NH
2
+


Cuinci |e cni|ine :cnc cIIivcIe :u||cne||c ver:c |c :c:IiIuzicne e|eIIrcfi|c crcmcIicc.
E perc verc che, IrcIIcncc:i ci unc reczicne che viene rec|izzcIc cLiIuc|menIe in
cmLienIe ccicc, in Ic|i ccncizicni |cmminc viene :c|ificcIc e |cIIivczicne
ce||cne||c ncn puc pi cvvenire.
Lc ce|ccc|izzczicne ce| ccppieIIc ccvuIc c||c :uc ccniugczicne ccn g|i e|eIIrcni
crcmcIici, che :i Ircvcnc :u crLiIc|i uc:i pcrc||e|i c ue||c ce| ccppieIIc:





Lc K ci Lc:iciIc ce||cni|inc hc un vc|cre ci 4,2 x 10
-10
menIre i vc|cri Iipici per |e
cmmine c|ifcIiche :cnc ce||crcine ci 10
-4
- 10
-5
.
Le cmmine crcmcIiche primcrie vengcnc c::iccIe cc||ccicc niIrc:c, HNC2, in unc
reczicne ceIIc d|ozotoz|one, fcrmcncc SALI DI DIAIONIO:




/nche |e cmmine c|ifcIiche primcrie ccnnc ue:Ic :Ie::c reczicne, mc i| prcccIIc
perce mc|Ic rcpiccmenIe N2 e i| ccrLcccIicne ri:u|IcnIe :i ceccmpcne ccncc
unc mi:ce|c ci prcccIIi. Le cni|ine, invece, ncn :i ccmpcrIcnc cc:| perch i|
ccIicne che ri:u|IereLLe cc||c perciIc ci czcIc ncn mc|Ic :IcLi|e e uinci i|
prcce::c |enIc: |cvcrcncc c freccc pc::iLi|e :cIIcpcrre i| prcccIIc cc unc
reczicne ci DIAIOCOFbLAIIONE primc che :i ceccmpcngc. Cue:Ic reczicne
|cIIcccc, :u| gruppc -NN
+
, ceg|i e|eIIrcni ce||cne||c ci uncmminc c ci un fenc|c:

N
H
H
..
NH
2
HNO
2
HCl aq 5C
N N
Cl
-

+
N N
OH
O
H
O
H
O
H
N N
OH
N N
+
+
+
+
H
+

l| ccmpc:Ic che :i cIIiene {un ozocomposto, ue||c in figurc :i chicmc 4-
|dross||en||ozobenzene) un COLOkANIE AIOICO. LimpcrIcnzc cei cc|crcnIi
czcici ri:iece ne| fcIIc che mccificcncc |e funzicnc|iIc c||e cue e:IremiIc ce||c
mc|ecc|c :e ne pc::cnc mccu|cre cc|cre e :c|uLi|iIc.