Slajd 1

Związki aromatyczne

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Slajd 2

Reguły aromatyczności

1. Związek musi posiadać cykliczną chmurę elektronowąponad i pod płaszczyzną cząsteczki

2. Chmura elektronów π musi zawierać nieparzystąliczbę 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

ener

gia

energiarezonansu

energiarezonansu

oczekiwana

oczekiwana

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Slajd 5

Cyklobutadien nie jest aromatyczny ponieważ maparzystą liczbę par elektronowych

Cyklooktatetraen nie jest aromatyczny ponieważ nie jestpłaski

cyklobutadien benzen cyklooktatetraen

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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 elektronówπ nie jest ciągła

2 pary elektronów πzwiązek nie jest

aromatyczny

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Slajd 8

Wielopierścieniowe związki aromatyczne

naftalen fenantren

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Slajd 9

Aromatyczne związki heterocykliczne

Związki heterocykliczne to związki cykliczne, w którychjedne lub większa liczba atomów węgla została zastąpiona innym atomem

pirydyna pirol furan tiofen

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Slajd 10

Pirydyna jest związkiem aromatycznym

struktura pirydyna

to jest orbital p

ta para elektronówznajduje się na

orbitalu sp2

prostopadłym do orbitali p

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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

karbokationprodukt przejściowy

związekaromatyczny

związekniearomatyczny

produkt addycjielektrofilowej

produkt substytucji nukleofilowej

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Slajd 13

Diagram energetyczny reakcji benzenu

postęp reakcji

Ener

gia

swob

odna

produkt addycji

produkt substytucji

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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 byćprowadzone przy użyciu nadmiaru AlCl3

bezwodnik kwasowy

chlorek acylu

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Slajd 19

Alkilowanie metodą Friedela-Craftsa

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Slajd 20

Przykłady pochodnych benzenu

amfetamina metaamfetamina„speed”

kwas acetylosalicylowyaspiryna

heksachlorofenśrodek dezynfekujący

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Slajd 21

Położenie dwóch podstawników zaznacza się cyframilub odpowiednim przedrostkiem

1,2-dibromobenzenorto-dibromobenzen

o-dibromobenzen

1,3-dibromobenzenmeta-dibromobenzen

m-dibromobenzen

1,4-dibromobenzenpara-dibromobenzen

p-dibromobenzen

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Slajd 22

Podstawniki wymienia się w kolejności alfabetycznej

1-chloro-3-jodobenzenmeta-chlorobenzen

nie1-jodo-3-chlorobenzen

meta jodobenzen

1-bromo-3-nitrobenzenmeta-bromobenzen

1-chloro-4-etylobenzenpara-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

m-butyliizopropylobenzen

kwas m-benzenodikarboksylowy

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Slajd 25

Dodawanie elektronów przez wiązanie σ nazywa sięefektem indukcyjnym

Grupa Alkilowa ma silniejszy efekt indukcyjny niż atomwodoru ze względu na hiperkoniugację

podstawnik oddaje

elektrony

podstawnik wyciąga elektrony

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Slajd 26

aktywujące dezaktywujące

kierują w pozycję orto i para kierują w pozycję meta

π Donor σ Donor Halogen Karbonyl Inne

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Slajd 27

toluen

najtrwalszy

najtrwalszy

orto

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Slajd 28

protonowanaanilina

najmniej stabilna

najmniej stabilna

orto

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Slajd 29

Substytucja elektrofilowa naftalenu

1-nitronaftalenα-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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