proprietati chimice compusi organici
DESCRIPTION
chimie organicaTRANSCRIPT
![Page 1: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/1.jpg)
Proprietati chimice alcani1. Reactia de halogenare
R-H + X2 → R-X + HX (X= Cl, Br)
CH4 + Cl2lumina CH3Cl + HCl
H3C CH3 + Cl2lumina-HCl H3C CH2Cl
![Page 2: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/2.jpg)
Proprietati chimice alcani2. Nitrarea alcanilor
CH4 + HONO2 → CH 3–NO 2+ H2O nitrometan
3. Reactia de izomerizare a alcanilor
H3C CH2 CH2 CH3 H3C CH CH3
CH3
50-1000C/ AlCl3
izo-butann-butan
![Page 3: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/3.jpg)
Proprietati chimice alcani4. Reactii descompunere:- reactii de cracare:
-reactii de dehidrogenare
H3C CH2 CH2 CH3
CH4 + H2C CH CH3
CH3-CH3 + CH2=CH2etan etena
propenametan
H3C CH2 CH2 CH3
CH2=CH-CH2-CH3 + H2
CH3-CH=CH-CH3 + H2
1-butena
2-butena
![Page 4: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/4.jpg)
Proprietati chimice alchene1. Reactiile de aditie -- au loc cu ruperea legaturii
π, cand rezulta compusi saturati• Aditia hidrogenului (hidrogenarea) CH2=CH2 + H2 CH3-CH3
• Aditia halogenilor (halogenarea) conduce la derivati dihalogenati vicinali
Ni
CH2=CH-CH2-CH3 + Cl2CCl4
H2C CH CH2 CH3
Cl Cl
1,2- diclorobutan
![Page 5: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/5.jpg)
Proprietati chimice alchene
• Aditia hidracizilor (hidrohalogenarea) decuge cu formarea compusilor monohalogenati
-alchene simetrice: nu este orientata
R-CH=CH-R + HX R CH2 CH R
X
compus monohalogenat
CH2=CH2 + HCl CH3-CH2-Cl monocloroetan (kelen)
![Page 6: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/6.jpg)
Proprietati chimice alchene-alchene nesimetrice: orientata conform
regulii MarkovnikovCH2=CH-CH2-CH3 + HCl H3C CH CH2 CH3
Cl
2-clorobutan (clorura de sec-butil)
CH3-CH=CH2 + HBr
fara peroxizi
cu peroxizi
H3C CH CH3
Br
H3C CH2 CH2Br
2-bromopropan
1-bromopropan
![Page 7: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/7.jpg)
Proprietati chimice alchene
• Aditia apei-(H2SO4)- conduce la alcooli
CH2=CH2 + HOHH3PO4, 3000C
70-80 atmCH3-CH2-OH
CH3 CH2 CH CH2 + HOH H+
t0CH3C CH2 CH CH3
OH2-butanol
![Page 8: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/8.jpg)
Proprietati chimice alchene2. Reactii de polimerizare - macromolecula
numita polimer
nApolimerizare
-(A)n-monomer polimer
n= grad de polimerizare
H2C CH
Z
npolimerizare
CH2 CH
Z
n
Z poate fi H (etena), CH3 (propena), Cl (clorura de vinil), CN (acrilonitril), OCOCH3 (acetat de vinil), C6H5 (stiren).
![Page 9: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/9.jpg)
Proprietati chimice alchene3. Reactii de oxidare
- Oxidarea blanda cu solutie apoasa neutra sau slab bazica conduce la formarea de dioli vicinali
R CH CH2 + [O] + HOHKMnO4
Na2CO3R CH CH2
OHOH1,2-diol
3CH2=CH2 + 2KMnO4 + 4H2O H2C CH2
OH OH
3 + 2MnO2 + 2KOH
1,2-etandiol
![Page 10: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/10.jpg)
Proprietati chimice alchene• Oxidarea energica (distructiva) cu KMnO4
R-CH=CH2 + 5[O] KMnO4/H+R-COOH + CO2 + H2O
R-CH=CH-R' + 4[O] KMnO4/H+R-COOH + HOOC-R'
R C CH2
R
+ 4[O] KMnO4/H+R C O
R
+ CO2 + H2O
R' CH C R
R
+ 3[O] KMnO4/H+R'-COOH + O C R
Rcetonaacid carboxilic
R C C R'
R R'
+ 2[O]KMnO4/H+
R C O
R
+ O C R'
R'
![Page 11: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/11.jpg)
Proprietatile chimice ale alchinelor1. Reactii de aditie
• Aditia hidrogenului : cis-alchene(hidrogenare partiala) sau la alcani(hidrogenare totala),in functie de catalizatorul folosit
R C C H + H2
Pd/Pb2+
R CH CH2
alchenaalchina
R C C H + 2H2
Ni
(sau Pd, Pt)R CH2 CH3
alcani
![Page 12: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/12.jpg)
Proprietatile chimice ale alchinelor• Aditia halogenilor (brom sau clor) la alchine conduce la
derivati dihalogenati nesaturati de tip trans sau la derivati tetrahalogenati
R C C R C CR
X
X
R
+ X2R C C R
X
X X
X
tetrahalogenoalcandihalogenoalchena (trans)
+ X2
![Page 13: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/13.jpg)
Proprietatile chimice ale alchinelor• Aditia hidracizilor (HCl, HBr) la alchine este catalizata
de HgCl2 si decurge in doua etape. Aditia la alchinele nesimetrice decurge conform regulii lui Markovnikov.
H3C C CH + HClHgCl22000C
H2C C CH3
Cl
+ HClH3C C CH3
Cl
Cl
2-cloropropena 2,2-dicloropropan
![Page 14: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/14.jpg)
Proprietatile chimice ale alchinelor• Aditia apei la alchine (hidratarea) sau reactia Kucerov
duce la compusi carbonilici: acetilena formeaza acetaldehida, iar omologii acetilenei formeaza cetone
HC C CH3 +HOHH2SO4
HgSO4
H2C C CH3
OH
tautomerieH3C C CH3
O
2-propenol (enol instabil) propanona
![Page 15: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/15.jpg)
Proprietati chimice arene
• Reactiile chimice ale arenelor pot fi clasificate astfel:
- reactii la nucleu: - reactii de substitutie; - reactii de aditie;
- reactii de oxidare;- reactii la catena laterala: - reactii de substitutie
- reactii de dehidrogenare - reactii de oxidare
![Page 16: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/16.jpg)
Reactii la nucleu 1. Substitutia
![Page 17: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/17.jpg)
Reactii la nucleu2. Reactii de aditie la nucleu
- Aditia hidrogenului
+
benzen
3H2Ni/ 1800C
ciclohexan
+ 2H2Ni +3H2
Ni tetrahidronaftalina decahidronaftalina
sau tetralina sau decalina
![Page 18: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/18.jpg)
Reactii la nucleu
• Aditia halogenilor- reactie fotochimica
CHHC
HCCH
CH
CH+3Cl2 lumina
H ClClH
ClHCl H
HCl
HCl
hexaclorociclohexanC6H6Cl6
![Page 19: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/19.jpg)
Reactii la nucleu3. Reactii de oxidare catalitica la nucleu
+9/2O2V2O5, 5000C-2CO2, -H2O
COOH
H
H
COOH-H2O
H
H CO
COO
acid maleic anhidrida maleica
+9/2O2V2O5, 3500C
-2CO2, -H2O
COOH
COOH-H2O
CO
COO
acid ftalic anhidrida ftalica
![Page 20: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/20.jpg)
Reactii la catena laterala1. Substitutia in pozitie benzilica
halogenarea
CH3
+Cl2, lumina
-HCl
CH2Cl
+Cl2, lumina
-HCl
CHCl2
+Cl2, lumina
-HCl
CCl3
toluen clorura de benzil clorura de benziliden triclorofenilmetan
![Page 21: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/21.jpg)
Reactii la catena laterala2. Oxidarea catenelor laterale alifatice
CH3
+ 3[O]KMnO4H2SO4
COOH
+ H2OCH3
CH3
+6[O]-H2O
COOH
COOHorto-xilen acid ftalic
CH2 CH3
CH2 CH2 CH3
+11[O]
COOH
COOH
+ CH3-COOH + CO2 + 3 H2O
![Page 22: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/22.jpg)
Reactii la catena laterala
3. Dehidrogenarea catenei laterale – Din etilbenzen rezulta stiren (feniletena)
C6H5-CH2-CH3 C6H5-CH=CH2 + H2
![Page 23: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/23.jpg)
Derivati halogenati- Reactivitate marita - halogenul in pozitia alilica sau benzilica
Cl CH CH2 Cl
Cl
H2C C CH CH2 Br
Br Br
reactivitate redusa
reactivitate maritareactivitate normala
- Reactivitate scazuta - halogenul la carbonul hibridizat sp2 sau sp - Reactivitate chimica normala - halogenul la un carbon saturat
![Page 24: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/24.jpg)
Derivati halogenati
- halogenul vinilic şi arilic au reactivitate scăzută (se realizează o legătură cu un parţial caracter de legătură dublă)
H2C CHCl
-CH2–CH+Cl
Cl +Cl
-
![Page 25: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/25.jpg)
Derivati halogenati
• halogenul alilic şi cel benzilic au reactivitate mărită (se realizează intermediari stabilizaţi prin conjugare)
CH2=CH–CH2 CH2–CH=CH2+ +
CH2 CH2
+
+
![Page 26: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/26.jpg)
Reactii de substitutie • Sinteza aminelor primare: RX + NH3 → R-NH2 + HX• Sinteza aminelor secundare: RX + R-NH2 → R-NH-R + HX• Sinteza aminelor tertiare: RX + R-NH-R → R3N + HX• Sinteza nitrililor: RX + KCN → RCN + KX• Sinteza omologilor acetilenei: RX + CH≡CNa → CH≡C-R + NaX• Sinteza Würtz a hidrocarburilor simetrice: RX + 2Na + RX → R-R + 2NaX
![Page 27: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/27.jpg)
• Sinteza alchilarenelor:
• Sinteza eterilor micsti: R’X + RONa → ROR’ + NaX;
RX + ArONa → ArOR + NaX• Sinteza alcoolilor:
R-CH2-X + HOHNaOH
R-CH2-OH + HX
C6H5Cl + NaOH3800C, 50 atm
C6H5-OH + NaCl
RX + C6H6
AlX3C6H5-R + HX
![Page 28: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/28.jpg)
Reactii substitutie
• Sinteza esterilor: R’X + R-COONa → R-COOR’ + NaX• Sinteza alcoolilor
R-CH2-X + HOHNaOH
R-CH2-OH + HX
C6H5Cl + NaOH3800C, 50 atm
C6H5-OH + NaCl
![Page 29: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/29.jpg)
Reactii substitutie
• Sinteza compusilor carbonilici
C6H5-CHBr2 + 2HOHHO-
C6H5 CH OH
OH
-H2OC6H5 C H
O
bromura de benziliden compus instabil aldehida benzoica
H3C C CH3
Br Br
+ 2HOHHO-
-2HBrH3C C CH3
HO OH-H2O
H3C C CH3
O
2,2-dibromopropan acetona
![Page 30: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/30.jpg)
Reactii substitutie
Sinteza acizilor carboxilici
C6H5 C Br
Br
Br
+ 3HOH- 3HBr
C6H5 C OH
OH
OH-H2O
C6H5 C O
OH
tribromofenilmetan acid benzoic
![Page 31: Proprietati Chimice Compusi Organici](https://reader033.vdocuments.mx/reader033/viewer/2022050619/577cc6e91a28aba7119f7fa7/html5/thumbnails/31.jpg)
Reactii eliminare
• Dehidrohalogenarea
H3C CH2
Br
KOH
alcoolH2C CH2 + HBr
H3C CH2 CH2 CH CH3
Cl
-HBrCH3-CH2-CH=CH-CH3
-HBrCH3-CH2-CH2-CH=CH2
2-bromopentan
2-pentena (80%)
1-pentena (20%)
Regula Zaitev: -se elimina preferential hidrogenul de la atomul de carbon dinpozitia β cel mai sarac in hidrogen