Documente Academic
Documente Profesional
Documente Cultură
OnclNrcA
fusctrrutwn
STTABEI.,E
lurie
Subotin
Anna
Tlohimciuc
UNIVERSTTATIATT}INICA A MOLDOV€I
FaorltateaTetmologiaAlimentelor
D€partamentulChimie
h.rrieSr.rbotin,
AnnaTrohimciuc
thi$neu 2017
Materialuldidacticinclusin lucrareadati €re drept scoprecapitular€ac€lormai importanteteme din cu6ul
de chimieorganicSla treaptapreuni\r€rsitari.
Autori:luri,eSubotln,conf.univ.,dr.
Ar la Trohlnaluc
Recenzent
AnSelaGurev,conf.univ.,dr.
Copertagiconceptiagrafid: AnnaTrohimduc
Subotin,lufi€
Chimiaorganici in schemegi tabele/ lurie Subotin,AnnaTrohimciuc;Univ.Tehn.a Moldovei,
FacultateaTehnologia
Alimentelor,
CatedraChimie.
- Chiginiu:Tehnica_UTM, 2017.-56 p.
50 ex.
lsBN978-997F45503-9
547(o7s)
s94
tsBN978-9975-45-503.9
CUPRINS
1 Configuratia electronic5
a atomuluide carbon 5
2 Teoriastructuriichimicea compugilor organici 6
3 Tipuride izomeriea compu5ilororganici 7
4 Modulde prezentarea formulelorcompugilororganic' 8
5 ALCANII 9
5.1 $irulomological alcanilor.proprietitilefizice 9
5.2 Nomenclaturaalcanilor 10
5.3 Proprietitilechimiceale alcanilor 'la
Qr
gl
hibridizarea- sp3
rl
-c-c-
eCI09
eeee
"....."-_-------
tt Patruotbltall Patruorbltallhlbrlzl(sD1
(s+3p)
nehibddlzall
hibridizarea- sp2
-C=C-
e.gg.g
--:-i-p
Trelorbltall
P' -->
909.
eee ----------------
tl
nehlb dlzatl{s+2p) hlb zl (spr)
Trelorbltall
- sp
hibridizarea eI .88 p; p,
--------------
'ee
GO
VV + ........,,.--.-.----.---
z
vl'
-c=c- p, \-!..-./
nehlbrldlzall(s+p)
Dolorbltallhlbrlzl(sp)
l'8*,.
Teoria
structurii
chimice
organici
acompusilor
Atomiiin moleculi suntlegati Proprietitilesubstanteisuntdeterminate
conformvalenteiintr-o anumiti ordine, nu numaide componenta moleculelor
ei,
numiti structurdchimicd, dar gide structuraacestota.
AleksandrButlerov
(1828-1886)
0rgantcl
rzoMERrA
or srnucrunA
DEFUNCTTUNE
deprezentare
Modut aformutelor organici
compu$itor
ACID
BUTAN IZOBUTAN CICLOHEXANIZOPROPANOL LACTIC
H H H
HH
CH"
De structuri cH3-cH-cH3
u^c'bh^
"t | "
cH3-cH2-cH2-cH3
semidesfisurati CH, H2C, ,cH2 il;3""-o"cH3-cH-cooH
OH
CH"
H\ /H H\ /H u$,n OH COOH
GraficN Ir
"),,-C...^-C,.
C
"{SJ-q.H I I
ff:.-{--.:fi -- }'-.-c-b-n H-f-cu, u-!-cH,
dil 'H
trldimensionaH X XH
HH HH H.H.H "? CH, CH,
\e
OE
Formuli
simplificati A A uoF"oo"
a[atcanito
omologic
$irut
FORMULA NUMARULSTAREA
STDENUMIREA DE TEMP. TEMP.
ALCANULUI IZOMERILOR
AGREGARE TOP.
Co FIERB.
CO
174
Teracontan -1013
=B
F-i
6
80
CroH,o, Pentacontan-10r8 60
-rt/l
93
C,ooHro, Hectan -103e
.tr lt5
ilolnenclatura
alcanilor
123
cH3-cH-cH3 2 - metilpropan
CH,
1234
cH3-cH-cH2-cH3 2 - metilbutan
CH,
3456
cH3-cH-cH2-cH2-cH3
,9H, 3 - metilhexan
'CH,
CH"
r lz': 4 s
c - cH2-cH-cH3 2,2,4- trimetilpentan
cH3-
CH, CH,
1234567
CH..
r
CH;
Ll
CH-CH"-
CH-CH"-
L I L
CH,,
r
+ CL-is*CCl4
CHCI, + HCI CHo+2O"* CO2+2H2O
cH3-cHr- c4- cH,{* CHr=CH- CH= CH2+2H,
Orldarea
bltndi
lnecdttisnul
rcacllei zctto*o,$ 2cH3oH
Clr* 91' * at ' inifierea
$ H-c(fl*np
orn+0, Dehidrogenarea
intermoleculari
CH,+Cl'*Ctt,'+tto
I propagarea
cq.+ cl,-cH3cl+cl.,|
)
zcno* o"*
lo,$zn- c( zn,o 2cHo
""'*' cH=cH+3q
;;:;..'#;;; intre,upe.,ea Conversia
metanului
cu.+u,ofrco+ru, lzomeizarea
l{itrarca oazderintezd (c> 4,f,Alcu
g P)
Konovalov,
{reacl.
Cracarea
termici cH3-cH2-cHr-cttr- cn, S cu3-cH- cHr- cHj
cttn+Houor$cH3Nor+Hp cB,o-f*cpr+crHo
etan etend
CH,
pebaz[
Sinteze demetan
I cr{,rrtninETrLAjr,l}rA
I I ccr,No;cloRoprcRrrA
I
I BEltzrNfiNTEncA
I
cl,h)
;ffi,ffi,
Glotutar€
I Ht'HrpRoGEr,r
I
I ct'unrircrtrE I
I cK.-DrcLoRoMErAN
I
lHcoficrpFoRMrcl@
t cocrr'osc"r
I@ ffiffi;l-- T.j----T_l
atcanilor
Utilizarea
F---,r,
E
[ aeu^Atc,-c,"1 |
@
(,
\Th4 I MATERTEPRn4AI
I PENTRU
srNrEzAI
G-fu
r,",-"^""1& @
w
Cicloalcani
Formulagenerald Metodele
deoblinere Proprietitichimice
l. Derlvall
dlhalogenafl
marglnall
al alcanllor
+Na 1.Pentruclcloalcanl
nestablll
CoHro{n>l)
,rCHz..tcrr,f,i----"., 7CH;CH, cH^
cH_ H.C - CH" H,t^,, --;;ffii*2N?j-H"c | +2Nacl * cH3-
cH,-cH3
'l
/\' | " .Lrz " \ct6ctt, "'*
HrC-CH, HrC-CH, ",/.ttcH^
-
ciclopropan
\//
ciclobutan 2. Hidrogenareaarenelor
n-sa_E*at, 9u;cH,-
c,H,
cicluriinstabile t{
tfo?t*sH.-'- t{, CH^
BT BT
Ht -
cH- ,Q$, 4f 9t' Hy'.ig,. cH3-
cH,-cH2I
2 H-C
'l CH- HCJH
H '-tC ",'
CH |' H,c.,.
H '"tC
rcH, 2. Clorularea
A I' ( g ,C
' H" CH CH,
H,C-CH, benzen ciclohexan ,S, ,{I,
ciclopentan ciclohexa-n
H.C
't CH" -. H^C CH-CI
z+cl^--su-
I "l | +HCl
\//
cicluristabile
sau
e) + 3H,_r_(---) HrC...
rCt,
'rC.,.
F,
3.Dehldrogenarea
alcanllor cH, cH:,
CH,
H,9 CH;CH,
tl
Irrc-cH,
ft"", 4CH;CH'-__
H"C.
-
- -9E'mit6;
\cHr-cHi '
TCH,CH'...
" H,C'
'
CHJH"
\CH,-CH,,'
3. Dehldrogenarea
H"C
'l
,!€,
CH" . HC' CH
,9!
metilciclopentan l ' - + *-' | ll +3H^
hexan ciclohexan HrCr HC\\,,CH
rCH,
,,['_'Lr" H HA
- \CHr-CH;
^__ ^-_rCH;CHrMndHrC.. ___ ___ pH-CH3
- \CH;CHrl
+H"
H"C-CH"' + 6 0
"l | 4CO2+4H2O
2-
1,2- dimetilciclobutan metilciclohexan lr2c- cH'
H a to g
9Jlg,9'f9fl, * p,rN
rNrocu,rEA
AroM,,.oR
DE
H,D'.GEN
D,N
A,cA,{,
cuAroM,
DE
HA,ocEN
Clasificarea Proprietififizice Proprietifichimice
Duplnumlrulatomilor
dehalogen Determinate
denatura Bazdalcalini(HrO)
(derivatl dF,trF,poli-halogenati)
mono-, gia radicalului
halogenului
cH3-cH2-cttpt +ron -89*cH3-cH'-cH'oH+KCI
. insolubiliin
HrO
I I . solubiliin
CrllrOH
H-C-Cl H-C-Cl . incolori,
volatili
I I cH3-cr!- cHcl,+2KoH-!8* cH3-cH2-c( ff +zrct +tr,o
H cl
(rl clorometan diclorometan
Utilizarea
FREoNI(CF,C|,,...) -!8* gu,- cH,-c<$" * ,*ct *
cH3-cH,-ccl3+3116g
Dupi poziliaatomilorde halogen . instalalii ",o
frigorifice,
stingerea
incendiilor
SoLVENTI CuNa(reactia
Wiirtz)
C4- CH - CH.- 1,2-dicloropropan
l- I (vicinalS)
ct ct CH,- CHr- Cl + 2Na+ Cl- CHr- CH3* CH3-CHr- CHr- CH,+ 2NaCl
Identificarea
cl probaBeilgein
I (alcool)
Bazialcalind
- cH" -colorarea
fldciriiln
cH.-
-l c 2,2-dicloropropan
(geminali) culoarea
verde CH3-CH,-CHrBr+KOH d*r, CH3-CH=CH2+
KBr+ HzO
cl
apetrotutui
fractionatd
Distilarea
GAZEUSOARE MOTORINA
(c,-q) (cr4-cro)
ETERDEPETROL ULEIDEAX
(c5-c6)
BENzTNA ULEIDEMOTOR
(c5- cll)
6) ucRorNA DECILINDRE
(c!- cr.)
PETROITAMPANT GUDRON
(cr2-crs) (> cro)
MOTORINA
(cr4-cro)
<@
GAZNATURAL
* rrr*Ot (> c2o)
Atchene
Izomeria Formula CoHro
generald Oblinerea
alchenelor
ln industrie
l. Depozilie l.Cracarea (f)
alcanilor
1tl1
CH;CH-CH;CH, but-1-end
t-entt
Nomenclatura CFr"*r-C"ILr+CF2"
CH;CH=CH-CH,but-2-eni CH;CH, etgq[(etilen;)
+Hp {H,
CH,-CH;CH;CHr-CH,.*CH,-CHr-CH3
2.Dehidrogenarea (to,Ni)
alcanilor
2.Decateni CHr=Cg-at, propqq(propilend) CJI,*,*CF#H,
l2t1
but-l'ena
CH;CH-CH;CH, CH'=CH-CH;CH3 but'l's41i CH,-CH,*HrC=CH2+ H2
3,Hidrogenarea (1",
alchinelor ft (P4Ni))
HrC=C-CH,2-m€tllpropeni *
C"Hr.r+H, C,H"
-.1 CH, Proprietififizice HC-=CH+ H,*HrC=CH,
C,- Co gaze ln labontor
3.Defun(iune(cucicloalcanii) 1.Dehidratarea (f, H,SQ
alcoolilor conc.)
C,-C, lichide
l{
Hidrohalooenarea t CO,+HrO
CH;CI!-CH=CH,+5[O]*CH3-CItr-COOH
@
Odiliedupl-regula
tlarcovnlcov)
CHr=91111 - CH3-CH,CI 3tol-CHifi -CH3+CH3-COOH
= CH-CH3+
CH3-C
"tt cloroetan CH, o
CH,-CH=CHr+HBr- CH:-CH-CH: 4[Ol- 2CH3-
CH,-CH= CH-CH3+ COOH
Br
2-bromopropan
Adigie
anti-Marcovnicov Reacfiidepolimerizare
CHr-CH=CHr+HBrP- CH,-CHr-CHpr (r,eTKI{A(Ctrl,l
r)
nCHr=CHr*(-Qt1-CHr-)" Polletilena
Aditiedeape(c H,Po.) propan-2-ol
CH,-CH=CI!+ HOH-CHr-!H- CHr
n CHr=CHr-911r*(*CHr-9H-) poliropilena
OH
CH,
Utilizarea
alchenelor
(urn&rnoreHr)
I or.oor.r'-,. I | ,or,r*or'rr*o
I I ;'.*"---_l
(o
I ;r"-T- l ffi
9rTEGUMELoR
lFRucrELoR I
Alcadiene
FormulageneraldCoHro_, Izomeria Obfinerea
l. Depozitie l.Dehidrogenarea (t",Crpr)
alcanilor
Nomenclatura n>3Gdienr) 1234
CHr=CH= 911-911, buta-1,2-dieni CH3-CH2-CHr-CHr*CI1r=911-gH=CHz+
2Hz
CH'=C=911, Pro'adieni
1234 1234
CHr=C=911-9113 buta-1,2-djgqi CH,=CH-Ql{=611, buta-1,3-dieni
CHr-CH- CHr-CHI CHr=g - 911=911,+2H,
CH, CH,
HibridizareasP' 2.Decateni
N
op, 8l 12145 2.Dehidrogenarea (f, MgOZnO)
alchenelor
o "1 "1
H.C=CH-CH=CH^ CHr=911- a"r- CH=CHz penta-1,4-dieni
CHr=C11-at,-CH,-CHr= Q11-CH=CHz+
Hz
1234
CH.,=
- l C-CH=CH,
2-metilbuta-1,3-diena
CoHu CH, gidehidratarea
3.Dehidrogenarea etanolului
buta-1,3-dieni (t",zno,A1203)
(cualchinele)
3.Defunctiune
HH HH
Proprietififizice r234
tt ttttl l
insolubilin
apa,
solubilin eter9ibenzen
-
2-metilbuta-l,3-dieni lichid
volatil;
1234
CH=C-911,-4", but-l-ind -CHz=CH-CH=CH,*2HrO* H,
insolubil
inap6,
solubilinmajoritatea
solvenlilor
organici
Proprietdfite
chimice
tEACl[ DEADflE
alealcadienelor
Hidrogenarea Hidrohalogenarea
(f, ft,-?4 Ni) _. r-----_CH,-CHCI-CH=CHz
CHr=Q]l-Qlf =CHr+Hr.*CHr-CH=CH-CH:
HCI-.1
CH"=f,H- Q11=CH,+
L_CH._CH=CH_CH.CI
Polimerizarea Halogenarea
(t., Na)
p- CHpr-CIIBT-CH=CHz
n CHr=Ql1-911=CH,* (- CHr- CU= CH- CHr-)n -t
CH,=CH-CH=CH"+Br"
I$
cauciuc (sintetic)
butadienic CHpr-CH=CH- CHpr
I
Vulcanizarea (t.,s)
cauciucului sI
...-cH"-cH- cH- cH--...
sI
...-CH.-CH=CH- CH.-,,.+...-CH"-CH=CH- CH^-...+ S * s
I
...-cH"-
' l cH- cH- cH^-...
sI
Atchine
Nomenclaturo
cini) Proprieti,tifizice
FormulageneraldCoHro_,CH=CH etfli(acetileni) Cr-Co gaze rputlnsolubile
ln aptr
CH3-C = CH ptopllq(metilacetileni) C,-C,, lichide *sulubile
ln solventi
organici
Izomeria 1234 C,r-... solide
CH=C-CH"-CH, but-i-ind
L Depozilie
a hgeturii
triple
Obtinerea
alchinelor - sp
Hibridizarea
1234 ,
CH=C-CHr-CH3 but-l-ine Acetilena
1,Din (1500'C)
metan
1234
CHj-C =C-CH, but-2-ini 2CHo*119=at * r"
N)
o) 2.Dincarburi
decalciu
2.Decatene CaCr+2Hp -*HC=CH+ Ca(OH),
(cao+3c2!eccac,
12345
HC= C-CHr-CHr-CH! +co)
pent-l-ine A|Ieatcntne
1234 1.Dehidrohalogenarea (Na0H/KOH,
dihalogenoalcanilor etanol)
HC=C-CH-CH3 CHr-CHr- CBrr- CH,+2KOHs CH; C= C-CH3+2KBr+ 2HrO
CH, 3-metilbut-1-ine 2,2-dibrombutan
CH,- CIIBr-CHBr-CHr+2KOHes{CII3-C= C-CH3+ 2KBr+ 2HrO
3.Defun4lune
cualcadlenele
2,3-dibrombutan
CHr=CH-Ql{=911, buta-I,3-dien6 2.Alchilarea
acetilenurilor
CH,-C = CNa+ Br - CrHr* CHr- C =ic -c2H5+NeBr
CH=C-CH,-CH. but-r-ine
propinilurA
desodiu 2-ini
Proprietttite
chimice
aleatchinelor
Reacfiideadifie Reac{iide substitufi€ ahidrcsenutuiacetitenic
Hldrooenarea Halogenarea CH=Ctt+2tAt*,),OH l-AgC =AgCl+4NH3+
(e [i, Pt] 2H,O
acetiluni
dediargint
HC=CH+
4-*CHr=CH, HC= CH+ Br2-CHBr= CHBr
CH!-C=CH+tAg(NH,)rOH
l*CH,- C=AgCl+2NII,+Hp
HC=CH+2H2-CH3-CH3 HC= CH+ 2Br,* CIIBTT-CHBr, propinilur;
deargint
Hidrohaloqenarea
(seaplicd
regula
luiMarkovnikov)
cl Reac{ii
deoxidue
I
CHj- C =CH+ ItCl-*CHr-C=CHz totali(ardere)
Oxidare
cl
N I 2CH=CH+
50,-4Cq + 240 + Q Q= 2800-3000"
s CHr-C=Ctt+
2HCl*CH"-
Jl
C-CH"
cl pa{iali
Oxidare
-cHr=CHcl
CH=CH+HCl
=cHlPlcn
H3c-c -c<fl"*co,
acidacetic
Hldratarea
(Hg'i H'SO.)
(reaqhKucerov)
c(f;"s.2gs,*
tt
cH H- ou*1n-
=cH+ Caan -. :l ".=.so+"$X-
tilil h.*t
tardehidEaceticd
acidoxalic
Reacfii (r,c)
detrimerizare
cH3- H- oH*
c=cH+ cnj*r:fi
[n;c=, lcrr=or-@
:",
Utilizarea
atchinelor
ACETII.ENA
w
| (r,z-aictoro6tan) |
t vtNtLAaEiitENn
I CH,=CH-C=CH
@ t"'=t"-tt
I I
i
N)
rc
I
-' ---
clonopnrru Jr
--'
b L
I eor-rcronunnoevrnrr.
(rl
I
Arene
Formulagenerald Izomeria Hibridizarea- sp2
cH"
{o >o)
CoHro_u
A;CH3 -trimetilbenzen
1,2,3
\lfcH,
Seriaomoloagi 9H"
9H, A;CH, '1,2,4
o o
-trimetilbenzen
\#'
CH, Ob[inerea
Denzen (toluen)
metilbenzen 1.Reaclia
Wurtz-Fitting
9H,-CH3 2NaCl
C.H,-C1+2Na+CH;Cl*Cp;CHf
N
o, cHr-cH3 9H, rAr 1-etil-3-metilbenzen
9H, 9H,
O*rr,,*t'@B'*run,
"tt
oo (arderc)
Oxidaretotali
2CF6+150'* 12CO'+
6Hp
Br
Reacfiideadifie parliali
Oxidare
9H'cl
N Aditiedehidrcgen inmediu
acid:
{
9H' @*ncr cH"
@+cr, 9H, 9H,
@*lr,*Q rC.** Cirt<8'*"p
o".Q 9H, 9H,
\:2
*,-4r0,
\,:t
Nltrarea
(H1{0, in mediuneutrugislab{azic:
HIor't.) NO.
@*r",*Q
fO]+no-no,*
\r/ fO]+n,o
, -\7 *.+-(/ --oH+2H'o
Aditiedehalogen ,4,7CH;CH, ,o. *c'-O
(-tr*" +co'
cl
9H, 9H' /A..' crrArcr
-\z r"o-"o,irl6l*o'
J6* \r +3no tvj*3cL*.,v.,
NO, cl
Utilizarea
benzenului
Alcooli
.
Formulagenerald /al
Denaomoroaga
le
Proprietifi fizice
metanol(alcool
metilic) Stareadeagregare
CH3-OH
(coH2o*2o)
coH2o*roH CH3- CHr- OH etanol(alcool
etilic)
Alcooliin staregazoasi
prezenlei
nusuntdinmotivul
legiturilordehidrogen.
CH3- CHr- CHr- OH (alcool
propanol propilic)
Alcoolii - lichizi.
inferiori Alcoolii - solizi
suoeriori
RR
Clasificarea
alcoolilor Izomeria
1.Dupi pozitiagrupei-OH cH" Depozitie g;ou",,u,.ri-.
F._ou,
6-
$._
o"'
t- 32r
CHr-CHr-OH Primar
cH"-
,I c -cH" CH3- CHr- CHr- OH ProPan-l-ol R R
Solubilitatea
in apl
N r23
(l) CHr- CH - CH, secundar OH
cH.-
' l cH-cH"
propan-2-ol Cucrettereacatenei scadesolubilitatea
in api
te4iar - -
OH OH C, Cr solubili in oriceproporlii
2. Dupitipul radicalului Cu(hexan-1-ol)- solubilitatea
0,6%
Decatena
cII3- CHr- OH saturat 4321 Miros
CH3- CHr- CHr- CHr- OH butan-l-ol
- mirosspecific
Alcooliiinferiori dealcool
CII,=CH-CHr-OH nesaturat - inodori
321 Alcoolii
suoeriori
CH"- - 2-metil-propan-l-ol
aromatic - l CH CH"- OH
A.oH Temperatura defierbere
v CH,
Dinmotivulprezentei legiturilordehidrogen,
3. Dupi numirulgrupelorhidroxil (cueteri) alcoolii
fierblatemierat-uriinalte
Defuncliune
Temperatura defierberecrestein sirul:
CH3-OH monohidroxiliciCHr- CH - CH, alcoolitd{iari
<alcooli ialcooliprimari
secundari
CH3- CHr- OH etanol
CH^-CH^ -dioli OH OH OH Densitatea
l" l' -trioli
OH OH CHr- O - CH3 eterdimetilic Densitatea
alcoolilor
< 1glcm3
alcoolitor.
0btinerea I
Fenotu ALCOOtI FENOtUt
Obfinereaalcoolilor Obfinerea
baziciaclobenzenului
Hidroliza
bazicia halogenalcanilor
Hidroliza
H-O @ on+Hrct
@cr* r.ruon--
cHicHpl + NaoH----!-cHiclt-oH + NaCl cataliticia izopropllbenzenului
oxldarea
alchenelor
Hidratarea
cH,=c1t-a"r*
"oH
-'- -"
H"SO.
cH3-9H-CH3
OH
cH3-9H-CH3
O *o,s& o OH
clinice
Propriettrfile
o
tl
+cH3-c-cH3
(r) glucozei
Fermentarea Metalele
alcaline
o
2CprOH+ 2Na*2CprONa+ H,
2CO,
Cp,rO.-2CfIrOH+
Bazele
alcaline
Reducerea gicetonelor
aldehidelor C.IITOH+NaOH* C.IITONa
+ HrO
Bromurarea
cr,-c(fl+n -!r*cHicHPH
o
OH OH
Br-/\- Br
1 3 8 1 2* + 3HBr
cH3-c - cq+ H,-Ni- g11,-
g11-gn, -7'
ooH Br
OH OH
Dingazuldesintezi
co+2[,^f6 cqon o o'N No'
,\r 1$1 +rnp
+lno-uo,ll%-
NO,
Propriet[tif.e
chimice
Reactiicuparticiparea
atomuluidehidrogen
din grupahidroxil Cu metaleleactive
Cumetalealcaline H,!-On H,C-ONa
2CH"OH
' + 2Na*2CH-ONa + H- 2 HC-OH+6Na*2 HC-ONa+3H^
metan'oat
desodiu' tl
Cu acizicarboxilici
Hp-oH H,C-ONa
n u+ .r
+ cH3-c<;H--::--
cH3-cH,-oH ctt,-c-:f,_a",_clr,+
H,o (glicerol) tripropanolatde
propan-I,2,3-triol sodiu
ester(acetat
deetil)
3fi5ii-o"-rel.cr,-c(fl
*np nf-opfl-No, H2c-o-No2
* H9-o-No2+}HP
Hc-oF{+Hol-No,
Arderea
CflrOH+3O,-2CO,+ 3Hp H2C-OFI HOI-NO, HrC-O-NO2
Utilizarea
alcootitor
(arcoorur
rruc)
I o.,o
o..r,. I I tot"*ll
t
f,;t
o)
N
$ cetone
Atdehide
Seriaomoloagl Metodele
deoblinere
Formulagenerald l. Oxidarea
alcoolilor ,.'
cH"-c-cH. -le* cn,-c(i +tt,
cH,-cH,-oH
tTfiSfir.to,'iar
'tl
(, | (mas6plastice,
materialde legiturd) |
(,l
@
Acizi
carboxitici
Formulagenenld Clasifi acizilorcarboxilici
carea Grupafunclionald
c"tt Duptr
numirulgrupelor
carboxil
Dupinatura
radicalului
*tb'
*\:Qt-nu-
"-,c<!, monobazici saturali
ginomenclatura
Izomeria .-o .-o
decateni
lzomeria
cH3-cioH cH3-cH'-cloH Propriet{ifizice
4 3 Z I ,-o acidetanoic acidpropanoic
(acidacetic) (acid
propionic) Proprietdlile in maremdsurd
fizice sunt
c4- cH,-cH,-cioH deprezenta
determinate legdturilor
dehidrogen:
(^)
(acidbutkic)
acidbutanoic bibazici nesatura!i 6- 6+
o)
O.-.
Ho..
--o......
3 2 1.-O - .rro R-C\o_fi...5//C-R
cH3-cH-cloH HO." "-OH CIr,=cr-c'(3n
cH3 acidoxalic RRR
(etandioic) acidacrilic ttl
(acid
izobutiric)
2-metilpropanoic
acid (propenoic) ccc
\\a. s* / \\6- 6, / \\6.
6+f
lzomeria (cuesterii)
defuncliune
polibazici aromatici ...H-o o...H-o o...H-o 0...
nttO deformarea
in api estecauzati
Solubilitatea
n
cH,-cq-c(;H H-c"-oH
'l /A-'"o dehidrogen
legiturilor cusolventul
.-O "-oH
H O - C -C i o H V
I I
acidpropanoic HC HC
Hrct acidbenzoic / /\\
.-o n..o ...H-O...H-O0...H-O...H-OO...
cH3-c:.o _cH3 "-oH
propo(ii
inH,0inorice
C,-Cr-sedizvoltd
acidcitric
demetil
etanoat
Proprietttite
chimice deobtinere
$imetodele AtEACtZttOR
CATBOXI.|CI
Proprietifichimice 4. Reaclia
deesterificare
cualcooli
-o -,o
1.Disoclatla aclzllor inferiori
in solutilapoase: crr,-c(i" +tto- cH,-cH,5". cn,-c(i_ a",_cH,+H,o
cH3cooH=cH3coo- +H*
acetatdeetil(etanoat
deetil)
2.Formarea sirurilorcu:
Metalele 5. Reacfla
dedeshidratare
intermoleculari
-,O .-O
C H 3 - C - \ C i-i i - i C H 3 - c l o - cH,-c(f," *"j). -.",* cH,-c(ooo;-c
-cH,+H,6
-H*"ri* cq-c_i)Mc+H,
cH3-
c\o=-"-'--' anhidridiacetici
(.^)
\ o kffi,jj,1."H.?ff1.;"")
{
Oxiziibazici Metodedeobfinere
CaO*(CH,COO),Ca+ Hp
2CH3-COOH+ t, Oxidarea
alcoolilor
Bazele ctt,-cu,-ottfcn;c(f,"
+ NaOH* CH,COONa
CHTCOOH + Hp 2,Oxidarea
aldehidelor
maislabi
Sirurileacizilor * cH,-c(f,"* zlgl +4NH3+
cr,- c(f, * zleg(NH),lon Hp
H2O+ CO2
NaHCOT-CHTCOONa+
CH3COOH+
3.Oxldarea
alcanilor
3.Cuclorul 5O,-4Cn;C(f," * zn O
2CHj-CH,-CH,-CH3+
^-- ^..O + ^..O
cHr-c(oH cl,- cHr-c(oH+ Hcl 4, Hidroliza
halogenoalcanilor
Cl acidcloroacetrc
cH3-c -cL+3KoHq",cH,-c-(f," * r"a, *
",o
Utilizarea
acizilor
carboxitici
ACIDUTMETANOIC ACIDULETANOIC ACIDULCITRIC ACtDUtACRtLtC
(FORMTC) (ACETTC)
Industriaalimentari
(conservantregulator
Medicin6 alaciditS!ii)
(actiunebactericidd) lndustriaalimentari
(aditivti conservant)
q) lndustriatextild
@ (prelucrareaprimar6 a fibrelor,hirtiei) Cosmetologie
lndustriachimici
(ob!inerea
acetalilor<elulozei)
Ermetezant
Industriapetroliera
(miclorareapH)
Sinteza
chimice
Constructie(component
al cimentului) Plastificator
Ob!inerea
esterilor
Esteri
Formulagenerald Proprietifichimice
Hidroliza
acidi
C"Hr"*ifr-O- CoHzo*r 5 cu,-
c(f,*.r.*nion
cH,- c'if,"* .",o"
o Hidroliza
bazicd
cr; c(! ia"" * u.ion*cH,-c(oo*u*
ctr,oH
Proprietilifizice
. Lichide volatile
incolore,
Ob[inerea
(o . Putinsolubiliin
api Interacliunea
acizilor
carboxilici
cualcoolii:
' < lglml
Densitatea -o
'-o
' Mirospldcut ur,-c(i" +tto'-cH,-cH,:" cu,-c( i _ a",_cn.*Hp
Nomenclatura Utilizarea
n PTASTIFICATORI AROMATIZATORI soLvENTl
t4r-rt "
" ".o-cHr-cH,
lndustriaalimenta16
Palfumerie
. metanoatul
deetil Cosmetologle
. esterul
etilic
alacidului
metanoic
. formiat
deetil
Esteri n-c( !" * no-n.a*n-c(!-***H,o
! -.o !!l7
u-r'.o
" --o-cH^-cH-cH- -o l1E-f'.
CH,-CH;CH;C(6-cu. cH,-cH;cH;c(3-."ra", "^'r " \o- cHz-cHr-cH-cH3
CH, CH,
Metanoat -il
de2-metiFpropan-1 Butanoat
demetil -il
Etanoatd6 3-metil-butan-1
formiatdeizobutil butiratdemetil acetatde izoamil
CRIZANTEM
tsfl
n-c(3_crr,-
o "-t(3-.",-.",- .",-.(3-(.",).-.",
O-t<3-.",b
Metanoatde benzil Metanoat -il
de2-feniFetan-1 depentilI
Etanoat Benzoat
debenzil
formiat
debenzil fomiat de 2-feniletil
Grisimi
UIiIAIAESIECDEGIICERIDE
Reacfiideoblinerea grlsimilor (esterificare)
cft-oHHo-c<flcu,-o-r<fl
+Ho-c<$-cn-o-c<$* ln,o
cH-oH
grisimilor
Clasificarea cHroHr*o-c(R,,
in,-o-c<fl"
glicerol acizicarboxilici grdsimi
supenon
ACtZtSATUnATI ActztI{ESATURATI
(Dr.domlnl '
ln gildml.nlm.lc)
Intrlt|ml Hidrolizagrisimilor (saponificare)
. oleic (CrTH3rcooH)
stearic (q7H35COOH)
palmitic(CT5HTCOOH) 1bgeturedubld
. linolic(C,'H3ICOOH) cr"-o-c1f;
- ,, CHTOII
2 legdtutiduble | drr^35
5 . linolenic(C|TH,9COOH) cH-o-c([.r"+ + 3CrrIssCOONa
3NaoH-.CH-OH
3 bgetu duble
. arahidonic (CrrH3lCOOH) d"r-o-c<!'n', iH;oHsteratoesodiu(sepun)
4legetui duble
grisimilor (lichide)
Hidrogenarea
cn,-o-c<!,n.. 9rr,-o-c(3,.s..
Proprietififizice Bc cu-o-c<!,g.
cn-o-c<! rr' +3H2Ni'
densitatea< 1glcm3
insolubile
in api
grisime+ api/proteine* emulsie (deex.lapte)
in,-o-c<!'n,, .n-"-.r3;.,
inodore,
incolore, fird (culoarea
gust 9igustulsuntcauzate
deimpurititi)
trioleoilglicerol tristearoilglicerol
grtrsimilor
Utilizarea
SAPUN
soLID/ LIGHID PARFUMERIE
PRODUSE
COSMETICE oBTTNEREA
GLTCEROLULUT
# fr fp.
-l;')
4rt
s
N
Formulagenerali-NH2 Izomeria
1.Decatene
CHr-CH-CH1NH, CH3-f-NH,
?",
Clasificarea
aminelor cH3-cHr-cHr-CH2-NH2
cH, cH3
butan-l-amini 2-metilpropan-2-amind
2-metilpropan-l-amin5
DUPANATURA
RADIcALULUI (butilamini) (izobutilamild) (te4-butilamini)
I
ALIFATICE
+
AROMATICE PRIMARE TERTIARE
2.Depozitiea grupei- NH,
cHr-cHr-cHr-NH, cH3-cH-cH3
cHr-l,II! NII. R-N-R prcpilamini NH"' izopropilamine
5 R-NH, I (propan-l-amind) (propan-2-amini)
cl) metilamina
cH3-NH-CF'
AV anilina
R
3,Gradul
desubstitutie
laatomuldeazot
(fenilamina) SECUNDARE
metiletilamina R_NH
H., zH H.. zCH^ H"C...
, N Z CH-
R N N,
I I I
cHr-cHr-cH3 cH2-cH3 CH,
5
s
3. R-NOr+ 6[H] !'stR-NHr+ 2Hp
cFsNOr+ 3H,rer cFs-NIIr+ 2Hp
'o'=F*_iltl
cu,-$* vn nu modificdculoareaindicatorilor
demetilamoniu
hidroxid
Proprietlfi fizice cuacizii
Interactiunea OxidareatotalS(arderea)
SoluJiile
apoase
L;I',N. ;**,ffi ;"3_:
conduccurentul sipotfi acide,
electric bazice
saunewre
CU alGoolli (romeazr
erterit
in funcliedenumdrul
gruieiorfuncfionale. NHr-cHr-
cooH+cu,ouf rctr-cHr-coocH3+
IIro
Pollcondensarea CuamOniacul
tormeazi.mtdet
-Orr
n,N-cu;c([_"+H_I_g{- NHr-Cfir-COOH+NHr*NH;CH,_COONHT+
HrO
glicina H alanina
H,o
:oo1r*H,N_or;ffi_cH_cooH+
CH,} dipeptidA
C", Intera4luneqlntramoleculari.
a grupelor
fun4ionale
-
5 CUmetale glele 0dentficarea.-anthoa(tztbO
pentruacldul8-amlnocapronic
-.I NHr-CHr-COOH*NH,-CHi CO,
,e
Proprietifigenerale CH;CH;CH;CH;gu,--I,!!",*",O
H-llili__
___ -,''.Nr'-*o
______HOl-c=o
Formarea
complecailor
t-€a prolactam
2R-cH-cooH+ lfF'.r,- o-ro
oton, '"z+ogAg2Lu-'--
-lp ",u..*
albastru-violet *tcaprolactam
- produsintermediar
pentruobtinerea
capronului
NH2
RCf Ctlf Xf ntf PfotGlcl 0den{fierea.mtnordroraron.rtct{ her.rodctid) Proprietifilegrupei- NH,
t"t'.tj. too"*
* nHo.-?:IIOf Cu aclzi tall (forme.d
struit)
' Ho^\" NH-
qalDen
",o -c";r.nr,* - cqun]l
ncr*l"$>c cr
"$)c
Cuacidulazotos
?')@'"n{*;cooH*znnon=*!}@cH;c,H-coot'ta*r"o
portocaliu
NH,-CH;COOH+
HNOr-HO-CH;COOII+N,+
Hp
aminoacizilor
Utilizarea
SINTEZA
PROTEINELOR
5
decarbon
}|idrati
ZAHARIDE
GIUCIDE.
Clasificarea
Hidraliidecarbon
ffi nuhidrolizeazi
@
I hidrolizeaziin maimultde l0|
moleculede monozahatide I
I I I
5 ++ @
I hidrolizeaziln de la2 oindla 10
|
T
f^.o""] || cetotrioze
"'"" II I moleculede monozbharide I
FI
I aldotrioze |
I aldotetroze
|
I aldopentoze
|
|cetotetroze
I
| cetopentoze
I
I | trLltF
I
I aldohexoze
| | cetohexoze
I [rr^*r* I
+t
:l
f iiSoza
++
^r"----.---.ar*;ll-.".--..-*l
I r.dr.d,.".I T."-*r-,.dtil[l
I mal-toz5- | | AFaroza I
I lactozi
celobiod
| | tregalozi I
I Aucoza fiucioza
|| I I I
Il^-*l iliHall
ii:$Jftr' I
Glucoza
Structura apoasiaglucozei
Tnsolulia sintprezente
toateformele
tautomere;
Propriet{ifizice
formaS-D-glucopiranozi
esteceamaistabili.
Glucoza
H H H OHH
"ra'o . Solidi
.Incolori
ttttt_o
H-C-C-C-C- C-C?7
njE-ou . Cristalini
ttttt-Ir
HOHOHO H OH
no-.:C-n H H
. Binesolubili
in api
n-:C-on HO HO . Dulce
Fructoza njC-oH
HHHOH H n-r6-on
I Oblinerea
glucozei
(Jr rrttt H glucoza
H-C-C-C-C-C-C-H formetautomere
tttt [l l.ln naturi
HOHOHO H O OH
9H,oH
H o 6CO,+
640,#:CFnO6+602
H
Izomeria
optice HO O HH ciclupiranozic
Formarea
zthuozei
0, -D-glucophanoza
HOH
-D-fructofu
ranoza
B
(,l
N
Proprietifichimice
H H
1.Hidroliza
zaharczei
HO
Hrso'r>
crrHrror+Hp cprp6+ cpno5 H oHo*tt,o H,SO.,fy' HOH
=(
glucoza ftuctoza qH,04 cH^oH^U\oH
r
fi\t uoltn"on
t-{
OHH
cuCa(OH)r,
2.Interactiunea Cu(0H),
( 3fi * Ho'cu
c,F,,o, -* c,p,ooo
-oH+ fi3) oF,oc,, <$.) co{'$ ) o,nz.c 2H2o
t2+
H'
I rl I
Amr00nut
pouzAHARrDA,
FORMATA UNIEpRtNtEGATUR|
DrNUNrrAilDED-CTUCOZA c{,.GUCOZ|D|CE
Formarea
amidonului Proprietifichimice
glucozei
Policondensarea Reac!ia
deidentificare
nCuH,rOu-* (C6H1oOj)J
nHrO
Amidonultratat
cuioddi o coloratie
albastri
Hidroliza
amidonului
(,
(, (c.Hroos) olzc,Fro,,4 ocF,p,
"g(cuH,oor),9
o-+ nHro amidon dextrine maltoza glucoza
(m<n)
OH H
legltura 0-glicozidici
Unitateastructuralia amidonului
Formarea
celulozei Proprietitichimice
glucozei
Policondensarea Hidroliza
celulozei
Ilso.
nCfl,pu * (CuHroOj)J
nHp (CF,'O')JnHpsoCrH,P,
cHroH cHroH cH,oH
H
H H H
OH OH OH H OH
O1...
H
H H
qHPH qqoH
(rl
s o glucoza
H
O\....+ trHrO
oII H
Nitrarea
celulozei
OHH OH
legiturap-glicozidici
I
3nrroNo, i H_$H; ,*o
it.n,"r'.Hfi]
n+ frcp,o,r ];
Unitateastructuralia celulozei
q40H Interacliunea
cuCH3COOH
o
H
o-......
OH H
.un,+fiff] -urQ- <P,ffi
3ncH,cooH
n l ; fnno, ]"*,*o
Utilizarea
amidonului
$icelutozei
INDUSTRIA
ALIruenrRRA FIBREARTIFICIALE PRoDUcEREA
HIRTIEI RcnrcurrunA
(hranaanimalelor)
(tl
(tl
r {[ v
.fr'^''
. -"C
t
CLASADE REACTN DE UASA DE w c'fII DE
COMPUSI IDEN'I'FIC,'RT SEMNE!j,R'ACTIEI (nMPU6t CLASADE REACTII
DE
IDENfIFICAPF (NMPUSI IDENTITICAXX SEMNELEREACTIEI
ALCAI{I
cLoRAtcA[l FEI'lOl
I
,9,*'.e""6*
I
J AMINE
Aedblodolo'n|d(l'+Md)
ftr lHu[
'
ALCHEI{E
sorqth*hnq (m.drqrdru)
34, . cH,! 2Me. + eup -
atcooLl
-ru,lt stut1 ,.@u. , sq,o rYr
4.et' rM.'
:r-*,^,"-'4.*j
34tu - I
_ u4/-\r?,,10
"'li GLUCOZA q\ ++q,.*,'o.aan4tu,
'k'ffiflttr'*^r*"'p
FRUCTOZA (o
ro
u'-c\i' aalqalot -
- *"-1" . ZAHAROZA
, ,,,o
ALCADIEIIE ALDEHIDE "a1,"uu,
*,-1i, aq*1.xo,a-
- *,-1" , ^,a. 'u*,. .u," Iii AMIDOI{UI
CEIULOZA
iLl '
fituaN | (urrl', + HNo)
,1.',c.a , cu...ttl.-u L
ALrcHll{G u . cu+2tar(NuJoq -
- Atc. cAtl+4N4\+2tto
U, actzl
cAa8ox-tcl AM[{OACtzl
I
."-"-,"
ucooq ' 44(^M)l toH 4
I )
fi
(t,2-Nea.hi@a-llht'a
h tuti! . hi'dtit /. tudi!)
HcooHzLca,l+2H,o
/
AREI{E
ldentificarea
compu$itor
0rgantct
tt