14.aromatic compounds. ( approx. lecture time: 2 lectures)
DESCRIPTION
14.AROMATIC COMPOUNDS. ( approx. lecture time: 2 lectures) Topics covered: 14.1-14.7A,14.7D,14.8A,14.9. Benzene. more than just cyclic conjugation: aromatic stabilization. Some Simple Benzene Derivatives. The Halifax Explosion of 1917. - PowerPoint PPT PresentationTRANSCRIPT
![Page 1: 14.AROMATIC COMPOUNDS. ( approx. lecture time: 2 lectures)](https://reader036.vdocuments.mx/reader036/viewer/2022062411/568166d5550346895ddae6df/html5/thumbnails/1.jpg)
14. AROMATIC COMPOUNDS. (approx. lecture time: 2 lectures)Topics covered: 14.1-14.7A,14.7D,14.8A,14.9.
Benzenemore than just cyclic conjugation: aromatic stabilization
![Page 2: 14.AROMATIC COMPOUNDS. ( approx. lecture time: 2 lectures)](https://reader036.vdocuments.mx/reader036/viewer/2022062411/568166d5550346895ddae6df/html5/thumbnails/2.jpg)
Some Simple Benzene Derivatives
![Page 3: 14.AROMATIC COMPOUNDS. ( approx. lecture time: 2 lectures)](https://reader036.vdocuments.mx/reader036/viewer/2022062411/568166d5550346895ddae6df/html5/thumbnails/3.jpg)
The Halifax Explosion of 1917The Halifax Explosion occurred on Thursday, December 6, 1917, when the city was devastated by the huge detonation of the SS Mont-Blanc, a French cargo ship fully loaded with wartime explosives, which accidentally collided with the Norwegian ship the SS Imo in "The Narrows" section of Halifax Harbour. About 2,000 people were killed and over 9,000 people were injured. The Halifax Explosion remains the World’s largest accidental explosion.
Picric AcidTNT; 2,4,6-trinitrotoluene
If you are from Nova Scotia, you will definitely know about it!
O2N NO2
NO2
CH3 OHNO2O2N
NO2
![Page 4: 14.AROMATIC COMPOUNDS. ( approx. lecture time: 2 lectures)](https://reader036.vdocuments.mx/reader036/viewer/2022062411/568166d5550346895ddae6df/html5/thumbnails/4.jpg)
The Phenomenon of Aromatic Stabilization
![Page 5: 14.AROMATIC COMPOUNDS. ( approx. lecture time: 2 lectures)](https://reader036.vdocuments.mx/reader036/viewer/2022062411/568166d5550346895ddae6df/html5/thumbnails/5.jpg)
Molecular Orbital Picture of the p Bonding in Benzene
![Page 6: 14.AROMATIC COMPOUNDS. ( approx. lecture time: 2 lectures)](https://reader036.vdocuments.mx/reader036/viewer/2022062411/568166d5550346895ddae6df/html5/thumbnails/6.jpg)
Mnemonic for Generating Molecular Orbital Energy Levels for Benzene
![Page 7: 14.AROMATIC COMPOUNDS. ( approx. lecture time: 2 lectures)](https://reader036.vdocuments.mx/reader036/viewer/2022062411/568166d5550346895ddae6df/html5/thumbnails/7.jpg)
Joining benzene rings to each other will always create an aromatic system!
“mothballs”
potent carcinogen
![Page 8: 14.AROMATIC COMPOUNDS. ( approx. lecture time: 2 lectures)](https://reader036.vdocuments.mx/reader036/viewer/2022062411/568166d5550346895ddae6df/html5/thumbnails/8.jpg)
Hückel’s 4n + 2 p Electron Rule
Hückel’s rule is concerned with compounds containing one planar ring in which each atom has a pz orbital as in benzene.
“Planar monocyclic rings containing 4n + 2 p electrons, where n = 0, 1, 2, 3, and so on (i.e., rings containing 2, 6, 10, 14 . .p electrons) should be aromatic, i.e., show exceptional stability relative to similar systems without this electron count”
![Page 9: 14.AROMATIC COMPOUNDS. ( approx. lecture time: 2 lectures)](https://reader036.vdocuments.mx/reader036/viewer/2022062411/568166d5550346895ddae6df/html5/thumbnails/9.jpg)
Examples of Hückel’s 4n + 2 p Electron Rule
Cyclooctatetraene
![Page 10: 14.AROMATIC COMPOUNDS. ( approx. lecture time: 2 lectures)](https://reader036.vdocuments.mx/reader036/viewer/2022062411/568166d5550346895ddae6df/html5/thumbnails/10.jpg)
![Page 11: 14.AROMATIC COMPOUNDS. ( approx. lecture time: 2 lectures)](https://reader036.vdocuments.mx/reader036/viewer/2022062411/568166d5550346895ddae6df/html5/thumbnails/11.jpg)
Imidazole
Imidazole is an aromatic compound that is important in biological systems. The two nitrogens are not equivalent! Learn how to tell them apart.
![Page 12: 14.AROMATIC COMPOUNDS. ( approx. lecture time: 2 lectures)](https://reader036.vdocuments.mx/reader036/viewer/2022062411/568166d5550346895ddae6df/html5/thumbnails/12.jpg)
The DNA Bases are Aromatic Compounds
![Page 13: 14.AROMATIC COMPOUNDS. ( approx. lecture time: 2 lectures)](https://reader036.vdocuments.mx/reader036/viewer/2022062411/568166d5550346895ddae6df/html5/thumbnails/13.jpg)
Sunscreens and Sunblocks(Organic chemists can become wealthy without making drugs)
Sunblocks: just “blocks” the sun’s rays. Use TiO2 and ZnO2. But will look geeky.
Sunscreens: organic compounds that converts the UV light into thermal energy. These are “designer compounds” so we can charge much more than inorganics. They also have many industrial uses!
PABA
Oxybenzone
Avobenzone
4-MBC
Tinosorb M
OOH
OCH3
O O
CH3O
OCH3
CO2H
NH2
NN
N
N
N
N
OH OH