Pertemuan 14

Karbon Siklik dan Diels Alder

Prof. Dr. Adel Zamri, MS, DEA
Ihsan Ikhtiarudin, M.Si
Sikloalkana
 Sifat Fisik Senyawa Karbon Siklik
Bp > Bp alkana rantai lurus
Mp > mp alkana rantai lurus
Alkana dan sikloalkana memiliki densitas <
dibanding alkena dan alkuna
Densitas sikloalkana > alkana
Bersifat non polar : tidak larut dalam air
Larut dalam benzena, CCl4, kloroform, dan
pelarut organik lainnya.
Sifat Fisik Sikloalkana
Tatanama
Cis dan Trans Sikloalkana
Senyawa Bisiklik
Tatanama Senyawa Bisiklik
Sintesis senyawa siklik:
Reaksi Diels Alder
Contoh:
THE DIENE MUST BE ABLE TO ADOPT
THE S-CIS CONFORMATION
O

rotate
+
reacts

s-trans s-cis
conformation conformation

does not O
react

+
reacts
normally
 DIELS-ALDER REACTION
HOMO (diene)
The reaction is
push concerted - all
of the orbitals
R are aligned in a
6-ring.

2
1 The HOMO
pull of the diene
donates elec-
trons into the
W LUMO of the
dienophile.

LUMO (dienophile)
BUTADIENE ETHYLENE

p4 The HOMO of the diene

donates electrons into
the LUMO of the
dienophile.

p3
LUMO
HOMO

p2
p*

p1 p
EXAMPLE - WITH ELECTRONIC FACTORS

O pull O
H3C H3C
CH3 CH3
push

H3C D H3C

Diene Dienophile A Cyclohexene

Works best if the dienophile The HOMO of the diene

has electron-withdrawing donates PUSHES electrons
groups, and the diene has into the LUMO of the dieno-
electron-donating groups. phile PULLS.
FORMATION OF A BICYCLIC COMPOUND

COOCH3 H
COOCH3
H3C D H
COOCH3
H3C COOCH3

COOCH3

H3C COOCH3
THE REACTION IS USUALLY STEREOSELECTIVE

H COOCH3

H COOCH COOCH3
3
H
H3C H3C
COOCH3 H

endo exo
The endo product
is usually preferred.

MeO H
It has been suggested
that the pi systems
like to establish O
maximum overlap
during the reaction. O H
OMe
 MORE DIELS-ALDER REACTIONS

D
CH3O CH3O

O O

O O
 O O

OH OH
OH OH
CH3O CH3O
O O

H3C H3C

H3C COOH H3C COOH

COOH COOH
OR

H3C HOOC

Retrosynthesis
H3 C HOOC
Latihan
Latihan
Latihan
Solusi
Latihan
Stereokimia
Ekso dan Endo
Latihan
Reaksi Diels Alder dengan
reagen tak simetris
Latihan
Solusi
Solusi
Latihan