prof. dr. mª del carmen clemente...
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Química II
5
OH
H2SO4 H + HSO4
-+
CH3 – C – CH2 – CH3|
CH3
L
sI
5.4 MECANISMO E1
CH3 – C – CH2 – CH3
|
H
+
HSO4
-
|
CH3
++ OH
-
+H
+
(H2SO4) (H2O)
a)
H2SO4 + CH2 = C – CH2 – CH3
|
CH3
b) CH3 – C – CH2 – CH3
+
|
CH3
|
+
HSO4
|
H
-
CH3 – CH2 = C – CH2 + H2SO4
|
CH3
+ OH-
+H
+
(H2SO4) (H2O)
Química II
6
5.4 MECANISMO Sn1 y E1
Br
CH3 – C – CH – CH3
|CH3
sI
Sn1
L
OH
CH3 – C – CH – CH3 + Br
|CH3
+
+-
-
Sn1
CH3 – CHOH – CH – CH3
|CH3
E1
CH2 – CH – CH – CH3 + Br
|CH3
-
|
HOH
+
-
+
E1
CH2 = CH – CH – CH3 + H2O
|CH3
a)
CH2 – CH – C – CH3
|CH3
+
|
H
b)
OH
+-
E1
CH3 – CH = C – CH3 + H2O
|CH3
Química II
10
H3C – CH = CH – CH3 + H+ H3C – CH2 = CH – CH3 + I+-
H3C – CH2 – CHI – CH3
a)
5.18
H3C – CH = CH – CH2 – CH3 + H+ H3C – CH2 – CH – CH2 – CH3 + +
b)
+ H3C – CH – CH2 – CH2 – CH3 + H+ H3C – CH2 = CH – CH3 + + -
+ 2I
+ H3C – CHI – CH2 – CH2 – CH3
CH2 = C – CH2 – CH3c)
|
CH3
+ H+
CH2 – CH – CH2 – CH3
|
CH3
+CH2 – C – CH2 – CH3
|
CH3
+
-+ 2I
CH2I – CH – CH2 – CH3
|CH3
*CH2 – CI – CH2 – CH3
|
CH3
+
CH3 – C = CH – CH3d)
|
CH3
+ H+
CH3 – CH – CH – CH3
|
CH3
+CH3 – CH – CH2 – CH3
|
CH3
+
-+ 2I
CH3 – CH – CHI – CH3
|CH3
*CH3 – CI – CH2 – CH3
|
CH3
+
Química II
11
CH2 = CH – CH – CH3 + H+ CH3 – CH – CH – CH3 +
+
e)
5.18 Cont.
+ CH2 – CH2 – CH – CH3 CH2 – CHI – CH – CH3 + CH2I – CH2 – CH – CH3
f)
-+ 2I
|
CH3
|
CH3
+
|
CH3
|
CH3
CH2 = CHBr + H+ CH3 – CHBr + CH2 – CH2Br + +
-+ 2I
CH3 – CHIBr + CH2 – CH2Br I
g) CH2 = C – CH – CH3|
CH3
|
CH3
CH2I = C – CH – CH3 + |
CH3
|
CH3
CH2 = CI – CH – CH3|
CH3
|
CH3
h) CH3 – C = CH – C – CH3
|CH3
|
CH3
|
CH3
CH3 – CI = CH – C – CH3 +
|CH3
|
CH3
|
CH3
CH3 – CI = CHI – C – CH3
|CH3
|
CH3
|
CH3
Química II
13
SUSTITUYENTES
DESPLAZAMIENTOS
ELECTRÓNICOS VELOCIDAD Q. INORGÁNICA
NUCLEOFÍLICOS R+
ACTIVANTES
FUERTES
ORTO Y PARA
DIRIGENTES
H + I+ ACTIVANTES
DÉBILES
ORTO Y PARA
DIRIGENTES
ELECTROFÍLICOS R-
DESACTIVANTES META
DIRIGENTES
HALÓGENOS R+
+ I-
DESACTIVANTES ORTO Y PARA
DIRIGENTES
EFECTOS DE LOS SUSTITUYENTES DEL
NÚCLEO AROMÁTICO EN LA SE
Química II
14
RENDIMIENTO (2) MAYOR QUE RENDIMIENTO (1)
(CAUSADO POR I-)
LA ORIENTACIÓN DE LOS HALOGNENO BENCENOS EN LA SE
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