![Page 1: CHM-134 ORGANIC CHEMISTRY CHAPTER-4: AROMATIC …](https://reader030.vdocuments.us/reader030/viewer/2022012020/61688d0ed394e9041f70801f/html5/thumbnails/1.jpg)
CHM-134 ORGANIC CHEMISTRYCHAPTER-4: AROMATIC COMPOUNDS
Asst. Prof. Gülbin KURTAY For more details please study: Organic Chemistry: Structure and Function Eighth EditionK. Peter C. Vollhardt (Author), Neil E. Schore (Author) ISBN-10: 1319079458
Benzene and Aromaticity
1825: Faraday discovers benzene by pyrolysis of whale oil: Colorless liquid bp ~80°C. Very unreactive
Cyclic structure: Kekulé /1865
Resonance:
![Page 2: CHM-134 ORGANIC CHEMISTRY CHAPTER-4: AROMATIC …](https://reader030.vdocuments.us/reader030/viewer/2022012020/61688d0ed394e9041f70801f/html5/thumbnails/2.jpg)
Asst. Prof. Gülbin KURTAY For more details please study: Organic Chemistry: Structure and Function Eighth EditionK. Peter C. Vollhardt (Author), Neil E. Schore (Author) ISBN-10: 1319079458
10.1 NOMENCLATURE RULESSubstituted benzenes: alkylbenzene, halobenzene, nitrobenzene, etc. (Functional groups have priority).
Disubstituted:
ortho meta para
![Page 3: CHM-134 ORGANIC CHEMISTRY CHAPTER-4: AROMATIC …](https://reader030.vdocuments.us/reader030/viewer/2022012020/61688d0ed394e9041f70801f/html5/thumbnails/3.jpg)
Asst. Prof. Gülbin KURTAY For more details please study: Organic Chemistry: Structure and Function Eighth EditionK. Peter C. Vollhardt (Author), Neil E. Schore (Author) ISBN-10: 1319079458
10.2 STRUCTURAL PROPERTIES
Regular Hexagon
![Page 4: CHM-134 ORGANIC CHEMISTRY CHAPTER-4: AROMATIC …](https://reader030.vdocuments.us/reader030/viewer/2022012020/61688d0ed394e9041f70801f/html5/thumbnails/4.jpg)
Asst. Prof. Gülbin KURTAY For more details please study: Organic Chemistry: Structure and Function Eighth EditionK. Peter C. Vollhardt (Author), Neil E. Schore (Author) ISBN-10: 1319079458
10.3 AROMATIC TRANSITION STATES
All are six electron transition states
![Page 5: CHM-134 ORGANIC CHEMISTRY CHAPTER-4: AROMATIC …](https://reader030.vdocuments.us/reader030/viewer/2022012020/61688d0ed394e9041f70801f/html5/thumbnails/5.jpg)
Asst. Prof. Gülbin KURTAY For more details please study: Organic Chemistry: Structure and Function Eighth EditionK. Peter C. Vollhardt (Author), Neil E. Schore (Author) ISBN-10: 1319079458
10.4 POLYCYCLIC BENZENOID HYDROCARBONS
![Page 6: CHM-134 ORGANIC CHEMISTRY CHAPTER-4: AROMATIC …](https://reader030.vdocuments.us/reader030/viewer/2022012020/61688d0ed394e9041f70801f/html5/thumbnails/6.jpg)
Asst. Prof. Gülbin KURTAY For more details please study: Organic Chemistry: Structure and Function Eighth EditionK. Peter C. Vollhardt (Author), Neil E. Schore (Author) ISBN-10: 1319079458
10.5 ANNULENES
![Page 7: CHM-134 ORGANIC CHEMISTRY CHAPTER-4: AROMATIC …](https://reader030.vdocuments.us/reader030/viewer/2022012020/61688d0ed394e9041f70801f/html5/thumbnails/7.jpg)
Asst. Prof. Gülbin KURTAY For more details please study: Organic Chemistry: Structure and Function Eighth EditionK. Peter C. Vollhardt (Author), Neil E. Schore (Author) ISBN-10: 1319079458
10.6 ELECTROPHILIC AROMATIC SUBSTITUTION (EAS)
1. Halogenation: F2 violent; Cl2, Br2 need catalyst; I2 endothermic
![Page 8: CHM-134 ORGANIC CHEMISTRY CHAPTER-4: AROMATIC …](https://reader030.vdocuments.us/reader030/viewer/2022012020/61688d0ed394e9041f70801f/html5/thumbnails/8.jpg)
Asst. Prof. Gülbin KURTAY For more details please study: Organic Chemistry: Structure and Function Eighth EditionK. Peter C. Vollhardt (Author), Neil E. Schore (Author) ISBN-10: 1319079458
10.6 ELECTROPHILIC AROMATIC SUBSTITUTION (EAS)2. Nitration with nitric acid
3. Sulfonation
![Page 9: CHM-134 ORGANIC CHEMISTRY CHAPTER-4: AROMATIC …](https://reader030.vdocuments.us/reader030/viewer/2022012020/61688d0ed394e9041f70801f/html5/thumbnails/9.jpg)
Asst. Prof. Gülbin KURTAY For more details please study: Organic Chemistry: Structure and Function Eighth EditionK. Peter C. Vollhardt (Author), Neil E. Schore (Author) ISBN-10: 1319079458
10.6 ELECTROPHILIC AROMATIC SUBSTITUTION (EAS)4. Friedel-Crafts reactions: Alkylation and acylation
A. Alkylation
B. Acylation - selective
![Page 10: CHM-134 ORGANIC CHEMISTRY CHAPTER-4: AROMATIC …](https://reader030.vdocuments.us/reader030/viewer/2022012020/61688d0ed394e9041f70801f/html5/thumbnails/10.jpg)
Asst. Prof. Gülbin KURTAY For more details please study: Organic Chemistry: Structure and Function Eighth EditionK. Peter C. Vollhardt (Author), Neil E. Schore (Author) ISBN-10: 1319079458
10.7 DONORS AND ACCEPTORSDonors activate
Acceptors deactivate
Activators: Send electrophile to the ortho and para positions
Deactivators: Send electrophile to the meta positions
![Page 11: CHM-134 ORGANIC CHEMISTRY CHAPTER-4: AROMATIC …](https://reader030.vdocuments.us/reader030/viewer/2022012020/61688d0ed394e9041f70801f/html5/thumbnails/11.jpg)
Asst. Prof. Gülbin KURTAY For more details please study: Organic Chemistry: Structure and Function Eighth EditionK. Peter C. Vollhardt (Author), Neil E. Schore (Author) ISBN-10: 1319079458
10.8 DISUBSTITUTED BENZENES
Substituent Effects are Additive
![Page 12: CHM-134 ORGANIC CHEMISTRY CHAPTER-4: AROMATIC …](https://reader030.vdocuments.us/reader030/viewer/2022012020/61688d0ed394e9041f70801f/html5/thumbnails/12.jpg)
Asst. Prof. Gülbin KURTAY For more details please study: Organic Chemistry: Structure and Function Eighth EditionK. Peter C. Vollhardt (Author), Neil E. Schore (Author) ISBN-10: 1319079458
10.9 STRATEGIES IN EAS
We can change the sense of the directing power of substituents
![Page 13: CHM-134 ORGANIC CHEMISTRY CHAPTER-4: AROMATIC …](https://reader030.vdocuments.us/reader030/viewer/2022012020/61688d0ed394e9041f70801f/html5/thumbnails/13.jpg)
Asst. Prof. Gülbin KURTAY For more details please study: Organic Chemistry: Structure and Function Eighth EditionK. Peter C. Vollhardt (Author), Neil E. Schore (Author) ISBN-10: 1319079458
10.9 STRATEGIES IN EASReducing agents:
H2, Pd, CH3CH2OH (hydrogenates carbonyl to alcohol, then cleaves the benzylic OH)
or Clemmensen Reduction Zn(Hg), HCl, Δ
Oxidizing agents:CrO3, H2SO4, H2O
![Page 14: CHM-134 ORGANIC CHEMISTRY CHAPTER-4: AROMATIC …](https://reader030.vdocuments.us/reader030/viewer/2022012020/61688d0ed394e9041f70801f/html5/thumbnails/14.jpg)
Asst. Prof. Gülbin KURTAY For more details please study: Organic Chemistry: Structure and Function Eighth EditionK. Peter C. Vollhardt (Author), Neil E. Schore (Author) ISBN-10: 1319079458
10.9 STRATEGIES IN EAS3. Friedel-Crafts reactions do not work with strongly deactivated benzenes (i.e., no activating substituents present):
4. Use reversible sulfonation for blocking certain positions