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Sintesis Senyawa Organik

Aldehida dan Keton

Nama Kelompok :

1. Berta Yuda Sisilia P. (131810301051)


2. Viki Amalia
(131810301053)
3. Laiqotul Lutfiyah (131810301041)

Reaksi dan Sintesis

da
i
h
e
d
l
A

Keton

Reaksi Adisi Nukleofilik

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

2. Addition of Grignard Reagents


R (
OH

R'' mGx or R'' Li

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

10. Oksidasi Aldehid


O

chromic acid, permanganate, Ag , etc

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. Reaksi klorida asam dengan


organometalik
O
C

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''

6. Sintesis Keton dengan 1,3Dithianes

thioacetal

(2) 1 R'-X

(1) BuLi

H , HgCl 2
S

R'

thioketal

H2O

C
R

R'
ketone

7. Sintesis keton dari Asam


Karboksilat
O
R

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%

2. Reduksi Klorida Asam


O
(1) LiAlH[OC(CH3) 3] 3
(2) H2O. H

(or Pd, BaSO 4, S)

Klorida Asam

Aldehida

Contoh :
NO 2

NO 2

(1) LiAlH[OC(CH3)3] 3 , -78


Cl

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

(2) H2O 2, NaOH

R
H

OH

Aldehyde

Enol (not isolated)

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