67
Isolated dienes
a
ordinary dienes
Conjugated dienes
b
Cumulated dienes
c
Pi
sp2-sp3
Pi
sp2-sp2
sigma
resonance
conformation of conjugated diene
sigma
(synperiplanar)
signal
s-trans
transoid
cis
s
s-cis
(antiperiplanar)
9.6kJ/mol
steric strain
s-cis
cisoid
trans
. conformations of dienes
_______________________________________________________
s-cis
s-trans
s-cis
69
C1
C2
_
, -unsaturated
C=C-C=O
s-trans s-cis
s-trans
s-cis
2-propenal
C4
C1
s-trans
s-cis
4-methyl-3-pentenone
. conformations of dienes
_______________________________________________________
_
s-trans s-cis
sp/ap
E/Z
N-alkyl amides
ethylene
bent bonds
CH2-
methylene
allene
sp
sp
sp2
trigonal geometry
H-C-H
71
H-C-H
(polyene)
trans cis
E/Z
. conformations of dienes
_______________________________________________________
_
dienes: 1,2-pentadiene , (E)-1,3-pentadiene , 1,4-pentadiene
heat of combustion: 3186 kJ/mol , 3217 kJ/mol , 3251 kJ/mol
a. ( Z, Z)-1,4-cyclooctadiene
b. ( E, E)-1,5-cyclooctadiene
c. trans-1,2-divinylcyclopropane
Pt
C6H10
2,3-dimethylbutane
73
a. 1,2-hexadiene , 1,,3,5-hexatriene , 1,3-hexadiene , 1,4-hexadiene ,
1,5-hexadiene , 2,4-hexadiene
s-trans
a. (E)-1,3-pentadiene
b. (Z)-1,3-pebtadiene
s-cis
. conformations of dienes
_______________________________________________________
_
a. (3E,5E)-3,5-octdiene
b. (1Z,3Z)-1,3-cyclooctadiene
c. 5-allyl-1,3-cyclopentadiene
d. 2,4-dimethyl-1,3-pentadiene
e. (E)-4-allyl-1,5-octadiene
f. cis,cis-3,5-octadiene
g. cis,trans,cis-2,4,6-octatriene
h. (1Z,3Z)-1,3-cyclooctadiene
i. cis,trans-1,4-dibromo-1,3-butadiene
j. (2E,7Z)-5-[(E)-1-propenyl]-2,7-nonadiene
platinum
C11H20
2,2,6,6-tetramethylheptane
E/Z
a. 3,4-octadiene
b. 2,4,6-octatriene
c.
d.
s-trans
75
s-cis
a. (2E,4E)-2,4-hexadiene
b. (2Z,4Z)-2,4-hexadiene
c. (2Z,4Z)-2,4-heptadiene
d. (Z)-1,3-hexadiene
a. 1,5-cyclooctadiene
b. 1,3-cyclooctadiene
c. 1,2-cyclodecadiene
d. 1,3,6-cyclooctatriene
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