1 Figure 18.1 Five examples of electrophilic aromatic substitution.

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Presentation transcript:

1 Figure 18.1 Five examples of electrophilic aromatic substitution

2 Electrophilic Aromatic Substitution Chlorination proceeds by a similar mechanism. Halogenation

3 Electrophilic Aromatic Substitution Generation of the electrophile in nitration requires strong acid. Nitration and Sulfonation

4 Electrophilic Aromatic Substitution Generation of the electrophile in sulfonation requires strong acid. Nitration and Sulfonation

5 Electrophilic Aromatic Substitution Chlorination proceeds by a similar mechanism. Halogenation

6 Electrophilic Aromatic Substitution Friedel-Crafts Alkylation and Friedel-Crafts Acylation

7 Electrophilic Aromatic Substitution Friedel-Crafts Alkylation and Friedel-Crafts Acylation

8 Electrophilic Aromatic Substitution Friedel-Crafts Alkylation and Friedel-Crafts Acylation [2]Rearrangements can occur. These results can be explained by carbocation rearrangements.

9 Electrophilic Aromatic Substitution Friedel-Crafts Alkylation and Friedel-Crafts Acylation

10 Electrophilic Aromatic Substitution Friedel-Crafts Alkylation and Friedel-Crafts Acylation Rearrangements can occur even when no free carbocation is formed initially.

11 Compounds containing two carboxy groups are called diacids. Diacids are named using the suffix –dioic acid. Metal salts of carboxylate anions are formed from carboxylic acids in many reactions. To name the metal salt of a carboxylate anion, put three parts together:

A variety of oxidizing agents can be used, including CrO 3, Na 2 Cr 2 O 7, K 2 Cr 2 O 7, and KMnO 4. Aldehydes can also be oxidized selectively in the presence of other functional groups using silver(I) oxide in aqueous ammonium hydroxide (Tollen’s reagent). Since ketones have no H on the carbonyl carbon, they do not undergo this oxidation reaction. Oxidation of Aldehydes

This reaction is used to prepare 1°, 2°, and 3° alcohols.