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Vertiefte Organische Chemie (Lehramt)

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Zusammenfassung/Mitschrift Vertiefte Organische Chemie für Lehramtskandidaten (VOCLA)

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  • January 30, 2024
  • 7
  • 2020/2021
  • Class notes
  • Dr. jan-philip wagner
  • All classes
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Addition
Die Addition kann als Umkehrung der verstanden werden
Eliminierung
"

:




gut polarisierten F- et
Eliminierung .
machen Alkene ZU Nukleophile
basisch
i

¢¢
r
- -
-


( =
c + H Br -




l d
r


H Br
sauer

Addition
Halogenalkan Alken


Elektrophile Addition AE Von HX

H H
%
'
S
.


ö I wir \
IÜI


¥




t H 4
ftp.C-C ,
t
schnell % Cy
- ' -




langsam ,
H
Carbenillmion


EnergieProfit
+ >

geschwindigkeitsbestimmend ThermoChemie :


^




A-
x

E + CP


: !!!
µ
"
""


¥ ⑦ C- H =
98 kcal Imd
- - - - - -
- - - -
H Produkte
THCI ¥Cl ④ C- Cl =
80kcal Imd


>
Reaktions Koordinate I = -


10kcal Imd
>E Wird frei
f- exotherm )
Relative Geschwindigkeiten
°


Nukleophile IT -




Bindung :

je elektronen reicher das Alken ,
desto schneller die AE



Stabilität des intermediären carbeniumions



Stärke des Elektrophile ( HU , HBR , HI Sind gut ,
HF ZU schwach )

Regioselektiv ität
¥ + Ha '


¥" kund nicht
¥

te ,
%
¥0 primäres
"
tert.carbehiumiony.tt
'
( INSTABIL ! )
carbenillmion

, > Stabilitäten von Carbeniumionen :




Benzyl =
AHH > tertiär > sekundär 1) primär →
Methyl )


Markovnikov -




Regel :
Bei der Addition von HX an nicht symmetrische Alkene addiert sich Ht

immer an das weniger substituierte c- Atom der
Doppelbindung .
Das höher substituierte


Halogen alkan ist das Hauptprodukt .




Stereochemie
Oberseite
µ 1
TÄTIG }
> v
-0
µ + H -


CI '
E- + Cl '
a :
Racemat
+


Unterseite N 1
:
HX -

Addition an 1,3 -

Diener



+ 2 Ha .

c, ,
knickt :




¥
( ,

^


Baren
×


Fündig

.




Addition
an
Endständige
tertiär -




taktisch
"
¥1
+ v

+ c! ICI Cl
c,
.



^



✓ '
höher substituiert tertiär
Doppelbindung
tttnicht :



¥)
Addition von Br, ich


¥, .
Ei! +
Ei! Kein cis Produkt ! )
-




trans
1 :
1

>
Stereospezifische anti -



Addition

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