aromatic electrophilic substitution 403221 aromatic 2 Resonance C

����� aromatic • ��� ������� ��� • ��������� electrophilic substitution 403221 -aromatic 2

Resonance ����� C 6 H 6 : 403221 -aromatic 4

Resonance ����� C 6 H 6 • ���� 6 p electron delocalize )��������� ( 403221 -aromatic 6

Aromaticity ������� • ��������� • ������� p-orbital ������� (���� conjugated double bond( • p electron delocalize ������ • ����� p electron ���� 4 n+2 (Huckel rule) – 2, 6, 10, 14 • ����� addition ����� aromatic ������� ion ������� cyclic conjugated system �� p electron ����� 4 n+2 403221 -aromatic 7

403221 -aromatic 8

403221 -aromatic 9

• ������ aromatic • ������ non aromatic 403221 -aromatic 10

�������� aromatic. 1����� acetylene. 2 Friedel-Craft alkylation . 3 Wurtz-Fittig reaction 403221 -aromatic 11

������ aromatic • Electrophilic aromatic substitution 403221 -aromatic 12

• ������� 1 ������� 2 rearomatization 403221 -aromatic 13

. 1 Halogenation 403221 -aromatic 14

������� 403221 -aromatic 15

. 2 Nitration ������� 403221 -aromatic 16

3. Sulfonation Fuming sulfuric acid = SO 3+H 2 SO 4 ������� 403221 -aromatic 17

. 4 Friedel-Crafts Alkylation 403221 -aromatic 18

������� 403221 -aromatic 19

. 5 Friedel-Crafts Acylation 403221 -aromatic 20

������� 403221 -aromatic 21

• ���������� electrophilic aromatic substitution. 1 Activating group = ��������� =ortho-, para- director 403221 -aromatic 22

ortho-attack para-attack Arenium ion ����� ortho-, para- attack �������� inductive effect meta-attack 403221 -aromatic 23

ortho- para- Arenium ion ����� ortho-, para- attack �������� resonance effect 403221 -aromatic 24

. 1 Activating group : ortho-, para- director resonance effect -NH 2, -NHR, -NR 2, , -OH, -OR, inductive effect -R, -Ar 403221 -aromatic 25

. 2 Deactivating group = ��������� = meta- director 403221 -aromatic 26

ortho-attack para-attack Arenium ion ����� ortho-, para- attack ��������� inductive effect meta-attack 403221 -aromatic 27

. 2 Deactivating group : metadirector 403221 -aromatic 28

. 3 Halogen • Deactivating group : X- ��� e- ��� inductive effect • ortho-, para- director : X- ��� e- ��� resonance effect ������� 403221 -aromatic 29

All unstable 403221 -aromatic 30

������ aromatic • ��������� 1. ����� oxidation 2. ����� Halogenation 403221 -aromatic 32

3. ����� Reduction ���� C=O 4. �������� organometallic ��� 403221 -aromatic 33

���������� ��� – m-chlorobenzoic acid – p-acetyltoluene – o-chloronitrobenzene – p-chlorosulfonic acid – m-ethyltoluene 403221 -aromatic 34