Nama Kelompok :
da
i
h
e
d
l
A
Keton
1. Addition of hydride
( O)
OH
C
R
NaBH4, CH3OH
or
H(R')
[1] LiAlH4; [2] H2O
H(R')
Contoh:
OH
O
[1] LiAlH4; [2] H2O
C
H3CH2C
H3CH2C
C
H
+ Li OH
or
[2] H2O
H(R')
H(R')
R''
Contoh :
O
[1]
C
H3CH2C
OH
Li
H3CH2C
[2] H2O
+ Li OH
3. Addition of
cyanideCN(
OH
NaCN
HCl
H(R')
H(R')
CN
Contoh:
OH
NaCN
C
H3C
HCl
H3C
C
CN
4. Wittig
R Reaction
C O
H(R')
Contoh:
Ph3P
R
C
(R')H
5. Addition of 1 amines
R
R
C O
H(R')
Contoh:
R''NH2
mild acid
N
(R')H
R''
6. Addition of 2 amines
NR2
R
C O
H(R')
R2NH
mild acid
(R')H
Contoh:
NH
H3C
C O
H3C
mild acid
N
C
H3C
+ H2O
CH2
7. Addition of H2O
hidration
H O
O
H or OH
OH
H(R')
H(R')
OH
Contoh:
O
H2O
C
H3C
CH3
OH
H
C
OH
8. Addition of alcohols
O
OR''
R''OH
(2 equiv)
H(R')
H(R') +
H2O
OR''
Contoh:
O
C
CH3OH
+ (2 equiv)
TsOH
OCH3
H3CH2C
H3CH2C
H + H2O
OCH3
9. Kondensasi Aldol
O
base
C
2 H3C
OH
H
H3C
C
H
CH2
OH
Contoh:
CHO
+
COOH
Na2Cr2O 7 / H2SO 4
ton
e
K
s
i
Sintes
1. Oksidasi alkohol
sekunder (2)
6+
Cr
dengan reagen
OH
base
C
2 H3C
H3C
R'
Contoh:
CH3
HO
H3C
CH3
K2Cr 2O 7
H3C
C
H3C
COOH
PCC
2 H3C
base
R
R'
Contoh:
O
C
H3CH2C
[1]CH3CuLi
Cl
[2] H2O
C
H3CH2C
CH3
3. Asilasi Friedel-Crafts
O
O
AlCl 3
C
R
Cl
R
acid chloride
Contoh:
O
O
AlCl 3
C
H3C
Cl
C
CH3
4. Hidrasi Alkuna
H 2O
C C H
alkyne
H2SO 4
HgSO 4
C
CH3
Contoh:
H3C
H 2O
H2SO 4
HgSO4
C
H3C
CH3
5. Ozonolisis
Alkena
R'
R
C
H
C
R''
(1) O 3
(2) (CH3)2S
R'
R
C
H
C
R''
thioacetal
(2) 1 R'-X
(1) BuLi
H , HgCl 2
S
R'
thioketal
H2O
C
R
R'
ketone
LiOH
OH
asam karboksilat
O
R
O Li
karboksilat litium
R'-Li
O Li
R
R'
dianion
H3 O
HO
OH
-H2O
O
R
R'
hidrat
keton
R'
1. Oksidasi Alkohol
is
Sintes
da
Aldehi
CrO 3
RCH2OH
piridina
RCHO
Alkohol
Aldehida
Primer
+
C5H5NH CrO 3Cl (PCC)
Contoh :
RCH2OH
RCHO
Alkohol
Primer
Aldehida
CH3(CH2)5CH2OH
CH3(CH2)5CHO
CrO3 . 2 N
1-heptanol
+
CH2 OH
CrO 3Cl
Heptanal
(84%)
O
CH
(PCC)
Cyclohexylmethanol
Cyclohexanecarbaldehyde
90%
Klorida Asam
Aldehida
Contoh :
NO 2
NO 2
O 2N
O
(2) H2O. H
O 2N
O
3. Gatterman-Koch Formylation
O
AlCl 3 , CuCl
HCl + CO +
O
C
CHO
Cl
O 2N
toluene
C H
benzaldehyde derivates
G = Hydrogen,
an Activating group
or halogen
Contoh :
CO, HCl
AlCl 3 , CuCl
H3C
p-methylbenzaldehyde (major)
(50%)
4. Hidrasi Alkuna
Hydroboration-Oxidation (anti Markovnikov Orientation)
R
(1) Sia2BH
R
H
OH
Aldehyde
Contoh :
C
C
CH2 C
(1) Sia2BH
(2) H2O 2, NaOH
ethynylcyclohexane
CH2
cyclohexylethanal
(65%)
O
C
5. Ozonilysis of Alkenes
R'
R
C
H
C
R"
R'
(1) O3
(2) (CH3)2S
+ O
Contoh :
+ S(H3C)2
R"
CH3
CH3
(1) O 3
(2) (CH3)2S
I -methylcyclohcxene
6-oxoheptanal
(65%)
6. 1,3 Dithianes
1,3-dithiane
(1) BuLi
(2) 1
Ralkylation
X
thioacetal
H3O , HgCl 2
Aldehida
k
n
a
h
T
Alhamdulillah
u
o
Y