Slajd 1 Związki aromatyczne

Slajd 1
Związki aromatyczne
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Slajd 2
Reguły aromatyczności
1. Związek musi posiadać cykliczną chmurę elektronową
ponad i pod płaszczyzną cząsteczki
2. Chmura elektronów π musi zawierać nieparzystą
liczbę par elektronowych
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Slajd 3
Reguła Hückela
Płaski i cykliczny związek aby mieć charakter
aromatyczny musi posiadać cykliczna chmurę
(4n + 2) elektronów π, gdzie n to liczba naturalna
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Slajd 4
oczekiwana
energia
oczekiwana
energia
rezonansu
energia
rezonansu
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Slajd 5
cyklobutadien
benzen
cyklooktatetraen
Cyklobutadien nie jest aromatyczny ponieważ ma
parzystą liczbę par elektronowych
Cyklooktatetraen nie jest aromatyczny ponieważ nie jest
płaski
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Slajd 6
Kation cyklopropenowy ma charakter aromatyczny
struktury rezonansowe kationu cyklopropenu
hybryda rezonansowa
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Slajd 7
sp3
sp3
cykloheptatrien
cyklopentadien
chmura elektronów
π nie jest ciągła
2 pary elektronów π
związek nie jest
aromatyczny
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Slajd 8
Wielopierścieniowe związki aromatyczne
naftalen
fenantren
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Slajd 9
Aromatyczne związki heterocykliczne
pirydyna
pirol
furan
tiofen
Związki heterocykliczne to związki cykliczne, w których
jedne lub większa liczba atomów węgla została
zastąpiona innym atomem
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Slajd 10
Pirydyna jest związkiem
aromatycznym
to jest
orbital p
ta para elektronów
znajduje się na
orbitalu sp2
prostopadłym do
orbitali p
struktura pirydyna
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Slajd 11
Przykłady związków
aromatycznych heterocyklicznych
chinolina
indol
imidazol
puryna
pirymidyna
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Slajd 12
Benzen jest nukleofilem, który reaguje z elektrofilem
produkt addycji
elektrofilowej
związek
niearomatyczny
produkt substytucji
nukleofilowej
karbokation
produkt przejściowy
związek
aromatyczny
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Slajd 13
Energia swobodna
Diagram energetyczny reakcji
benzenu
produkt addycji
produkt substytucji
postęp reakcji
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Slajd 14
Halogenowanie benzenu
bromowanie
bromobenzen
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Slajd 15
Nitrowanie benzenu
kwas azotowy
jon nitroniowy
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Slajd 16
Sulfonowanie benzenu
kwas siarkowy
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Slajd 17
mechanizm desulfonowania
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Slajd 18
Acylowanie metodą Friedela–Craftsa musi być
prowadzone przy użyciu nadmiaru AlCl3
chlorek acylu
bezwodnik kwasowy
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Slajd 19
Alkilowanie metodą Friedela-Craftsa
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Slajd 20
Przykłady pochodnych benzenu
amfetamina
metaamfetamina
„speed”
kwas acetylosalicylowy
heksachlorofen
aspiryna
środek dezynfekujący
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Slajd 21
Położenie dwóch podstawników zaznacza się cyframi
lub odpowiednim przedrostkiem
1,2-dibromobenzen
orto-dibromobenzen
o-dibromobenzen
1,3-dibromobenzen
meta-dibromobenzen
m-dibromobenzen
1,4-dibromobenzen
para-dibromobenzen
p-dibromobenzen
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Slajd 22
Podstawniki wymienia się w kolejności alfabetycznej
1-chloro-3-jodobenzen
meta-chlorobenzen
nie
1-jodo-3-chlorobenzen
meta jodobenzen
1-bromo-3-nitrobenzen
meta-bromobenzen
1-chloro-4-etylobenzen
para-chloroetylobenzen
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Slajd 23
Halogenowanie łańcucha bocznego
propylobenzen
1-bromo-1-fenylopropan
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Slajd 24
Utlenianie łańcucha bocznego
toluen
kwas benzoesowy
kwas
m-benzenodikarboksylowy
m-butyliizopropylobenzen
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Slajd 25
Dodawanie elektronów przez wiązanie σ nazywa się
efektem indukcyjnym
Grupa Alkilowa ma silniejszy efekt indukcyjny niż atom
wodoru ze względu na hiperkoniugację
podstawnik
oddaje
elektrony
podstawnik
wyciąga
elektrony
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Slajd 26
kierują w pozycję orto i para
π Donor
σ Donor
aktywujące
kierują w pozycję meta
Halogen
Karbonyl
Inne
dezaktywujące
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Slajd 27
orto
najtrwalszy
toluen
najtrwalszy
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Slajd 28
orto
najmniej stabilna
protonowana
anilina
najmniej stabilna
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Slajd 29
Substytucja elektrofilowa naftalenu
1-nitronaftalen
α-nitronaftalen
1-bromonaftalen
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Slajd 30
Substytucja w pozycji 1 naftalenu jest łatwiejsza,
podstawiony w pozycję 2 naftalen jest trwalszy.
niekorzystne
oddziaływanie steryczne
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