Chapter 16 - Chemistry of Benzene: Electrophilic Aromatic Substitution

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Electrophilic aromatic substitution

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Electrophilic substitution example

  • The goal is to stabilize everything

<ul><li><p>The goal is to stabilize everything </p></li></ul><p></p>
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Aromatic nitration

  • usually forms water as a by product

<ul><li><p>usually forms water as a by product</p></li></ul><p></p>
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Alkylation reaction

Called Friedl-Crafts alkylation reaction

  1. Carbocation is created when reacting with AlCl3

  2. Now the carbocation can react with a ring.

  3. Extra H can be used to stabilize AlCl3

Because a carbocation is formed, carbocation rearrangement can happen, particularly when a primary alkyl halide is used. (Hydride and methanide shifts)

<p>Called Friedl-Crafts alkylation reaction</p><ol><li><p>Carbocation is created when reacting with AlCl<sub>3</sub></p></li><li><p>Now the carbocation can react with a ring. </p></li><li><p>Extra H can be used to stabilize AlCl<sub>3</sub></p></li></ol><p>Because a carbocation is formed, carbocation rearrangement can happen, particularly when a primary alkyl halide is used. (Hydride and methanide shifts)</p>
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Acylation reaction

  • Because of the resonance stabilized acyl cation, no carbocation rearrangement occurs during acylation.

<ul><li><p>Because of the resonance stabilized acyl cation, no carbocation rearrangement occurs during acylation. </p></li></ul><p></p>