karbanion dan reaksinya
TRANSCRIPT
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Karbanion dan Reaksinya
Rima Chintami PaultyJeremy Fransisco Pakasi
Muhammad Fajrin A. SalimAgres Krismantona Tarigan
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Pembentukan Karbanion
R3C H B R3C BH
Karbanion adalah karbon yang memiliki pasangan elektron yang menyendiri (karbon yang bermuatan
negatif)
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R3C X Y XYR3C
Cara yang paling sering untuk membentuk karbanion adalah dengan penyingkiran suatu atom atau gugus X dari karbon, X
meninggalkan pasangan elektron ikatannya:
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R C OO
CO2R
Ph3C Cl Na/Hg Ph3C Na
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RM R'I RI R'M
Ph3C H Na NH2NH3
cair Ph3C Na NH3
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Pemantapan Karbanion
Faktor-faktor pemantap karbanion:1. Peningkatan sifat s karbon karbanionnya
Kenaikan keasaman ini tampak dari alkena ke alkuna. Ini dapat dilihat dari peningkatan sifat s orbitall hibrida yang terlibat dalam ikatan dalam H, yakni sp3 < sp2 < sp1.
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2. Gejala/pengaruh imbasan tarikan elektronterlihat pada HCF3 (pKa = 28) dan HC (CF3)3 (pKa = 11).
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3. Konjugasi pasangan-bebas (lone pair) karbanion dengan suatu ikatan rangkap. Misalnya CN, C=O, NO2, dan CO2Et.
CHCH2
BN NCH2 C CH2 C N BH
OHCH2
B NO
NO
OCH2 CH2 ONO
BH
BHCH2 OC
MeCMe
OCH2 CH2 OCMe
BH pKa = 20
pKa = 10,2
pKa = 24
pKa = 25
BHOCH2 COEt
CH2 OCOEt
COEt
BHCH2 O
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H H
+BH
B
4. Aromatisasi
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10.3 Konfigurasi Karbanion
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10.4 Karbanion dan Tautomeri
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10.4.1 Mekanisme Antarubahan
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10.4.1 Mekanisme Antarubahan
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10.4.2 Laju dan struktur
R3C H + BK1
K -1
R3C BH +
( K = k1/k -1 )
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10.4.3 letak kesetimbangan dan struktur
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Penambahgugusan
• Karbonasi
CO O
R M
R CO
O M
C C
H Me
LiCO2
BrMeLi
Me
MeH
CCLi
Me
MeH
CC
CO2
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Penyingkirgugusan
• Dekarboksilasi
PhSO2CH
B H
CH2
Y
PhSO2CH
Y
CH2 PhSO2CH CH2
O C
O
R CO2 + RH
R HLambat Cepat
Laju = k RCO2
O
CO CMeNO2 CO2 +
Me2C N O
ONMe2C
O
O
H Me2CHNO2
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Me2CNO2 Me2CNO2
Br BrBr
+ Br
H
O
CH2
MeCH3C
HH
O
C
CH2
O OO
CH2MeCC
O O Me O
C C
CO2O
+ C
O
Me
H+CO2O C
O
CH2COMe
CH2 CMe
CH3COMe
O
CH2
O
CMe
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CH2
C
O
C
H
CR2
R O
C C
CH2
O
H
CR2
R
CC
O
O
H
CH2 R
CR2
O
NNH
NH
N
H O PhCOMe
HO
C
NH
ON
O
C
O
H
CPh
Me Me
PhC
O
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Pemindahan
• Pertukaran Deuterium
• Nukleofil Karbanion
CPhMeEtC
H
O
ODLambat
MeEtC
O
CPh
MeEtC CPh
O Cepat
D2OO
D
MeEtC CPh
(+) (+)_
(MeCO)2CH2OEt
R Br(MeCO)2CH (MeCO)2CH+ +RBrR Br
HC CHNH2 CHC
RBr+ BrR HC C BrR +
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R MgBr
CH(OEt)2
OEt
RCH(OEt)2H / H2O RCHO
RCH2CH2 Cl RCH2CH2 Na2Na BrR' RCH2CH2R'
RCH2CH2
H
RCH CH2
Cl Na
RCHCH2
RCH2CH2
H
+ Na Cl
+-
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R
EtO2C
H
Cl
MeO
EtO2C
R
Cl R' R'
C
O
EtO2CEtO2C
R
R'Cl
OR'R O R'
R'
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OH
O
CCl2H
CCl2
O OCHCl2
OH
OCHO
H
OHCHO
o- aldehida (salisilaldehida)
Reaksi Reimer-Tiemann
Reaksi yang melibatkan karbanion aril yang terdelokalisasi
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O
Me
HO
Me
HO
Me
CCl2CCl2 berlebihan
CHCl2Me
OO
Me CCl2Me
O
OHCHO
Me
CCl2
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HO
C
O
O
HO
CO2
OHCO2
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Penyusunan-Ulang
C C
R R
CC
KP Karbokation KP Karbanion
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Ph3C CH2Cl Na Ph2C
Ph
CH2 Na Ph2C CH2
Ph
Na
ROH
CO2
Ph2C
H
CH2Ph
Ph2C CH2Ph
CO2 Na
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Me2N
Me
CHPh
HPhLi
Me2N CHPh
Li
Me
Me2N CHPh
Me
MeS
CH2
CHCOPh
H
Ph
OH
Ph
CHCOPh
CH2
MeS MeS
CH2
CHCOPh
Ph
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PhHC
H
O
CH2ClC
HO
OH CCH2
O
PhHC Cl PhHC
O
CH2
C
HO
CCH2PhHC
OHO
PhCH CH2
CHO O
PhCH2CH2CO2
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Oksidasi
Ph3C NaO2
Ph3C NaO2
(MeCO)2CH
(MeCO)2CH
I2 (MeCO)2CH
(MeCO)2CH (MeCO)2CH
(MeCO)2CH
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Halogenasi Keton
MeEtC
H
CPh
OOH
lambatMeEtC CPh
O MeEtC CPh
Hal
O
MeEtC CPh
D
OD2O
cepat
𝛿−
𝛿−
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R CH
H
C
O
CH2
2 1H OH
OH
1
2
lambat
RCH2C CH2
O
RCH2C
O
CH2
R CH CCH3
O O
CHR CCH3
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R CH
H
C
O
CH2
2 1H OH
OH
1
2
lambat
RCH2C CH
O
RCH2C
O
CH
R CH CCH2Br
O O
CHR CCH2Br
Br
Br Br
RCH2C
O
OH
CX3OH
RCH2C
O
OH
CX3 RCH2C
O
OH
CX3
O
O
RCH2C HCX3
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CH3 CMe
O H AHA
A
CH2
H
CMe
O HA
lambat
Br Br
CH2 CMe
O H ABr2
Br Br
CH2 CMe
O H A
RCH CMe
OHBr2
RCH CMe
O
Br
RCH2C CH2
OHBr2
RCH2C
O
CH2
Br
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TERIMAKASIH