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Chapter 18
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm ...
The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In ...
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide. The ...
In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound. Many functional groups can be ...
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence ...
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are ...
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the ...
Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming ...
Friedel–Crafts reactions were developed in 1877 by the French chemist Charles Friedel and the American chemist James Crafts. Friedel–Crafts ...
The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic ...
Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon ...
Ortho–para directors are substituent groups attached to the benzene ring and direct the addition of an electrophile to the positions ortho or para ...
Substituents on the benzene ring that direct an incoming electrophile to undergo substitution at the meta position are ...
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons ...
Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through ...
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive ...
When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the ...
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the ...
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as ...
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The ...
Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take ...
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of ...
Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high ...
The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of ...
In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The ...
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![18.12 : Directing Effect of Substituents: ,[object Object],–,[object Object],-Directing Groups](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12470.jpg)
![18.13 : Directing Effect of Substituents: ,[object Object],-Directing Groups](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12471.jpg)
![18.14 : [object Object],–,[object Object],-Directing Activators: –CH,[object Object],, –OH, –NH,[object Object],, –OCH,[object Object]](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12472.jpg)
![18.15 : [object Object],–,[object Object],-Directing Deactivators: Halogens](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12473.jpg)
![18.16 : [object Object],-Directing Deactivators: –NO,[object Object],, –CN, –CHO, –CO,[object Object],R, –COR, –CO,[object Object],H](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12474.jpg)
![18.18 : Nucleophilic Aromatic Substitution: Addition–Elimination (S,[object Object],Ar)](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12477.jpg)
![18.20 : Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic S,[object Object],1](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12479.jpg)
