Electrophilic Aromatic Substitution

Crampton, Michael R.

doi:10.1002/9781118560273.ch6

Cited by 3 publications

(2 citation statements)

References 135 publications

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“…Undergraduate textbooks summarize the kinds of electrophiles used in the S E Ar reaction, including halogenation, nitration, sulfonation, and the Friedel−Crafts reaction. 8 By taking advantage of a Lewis acid as the catalyst, the reaction could work on the electron-neutral aromatic ring. However, electronrich benzenes, such as anisole and aniline, are welcomely applied in undergraduate experiments to save the reaction duration and avoid the use of corrosive Lewis acids.…”

Section: ■ Principle Electrophilic Aromatic Substitution Reactionmentioning

confidence: 99%

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Two-Step Synthesis of 4-Hydroxy-3,5-dimethylphenyl Benzoate: Undergraduate Organic Laboratory of Electrophilic Aromatic Substitution and Nucleophilic Aromatic Substitution

Han,

Qin,

Wang

et al. 2024

J. Chem. Educ.

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Electrophilic aromatic substitution (SEAr) and nucleophilic aromatic substitution (SNAr) reactions are among the most valuable reactions in the conversion of aromatic rings. While these reactions are typically covered in separate experiments in undergraduate organic courses, a continuous experimental setup elucidating both SEAr and SNAr processes remains unexplored in the literature for undergraduate laboratories. We herein described a two-step experimental design to cascade the SEAr and SNAr reactions, aiding students in better understanding the similarities and differences of these conversions as well as introducing the concept of umpolung. The experiment also reinforces students’ proficiency in fundamental organic synthesis techniques and workup procedures, such as TLC analysis, chromatography purification, recrystallization, and handling LRMS and NMR.

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Section: ■ Principle Electrophilic Aromatic Substitution Reactionmentioning

confidence: 99%

“…Undergraduate textbooks summarize the kinds of electrophiles used in the S E Ar reaction, including halogenation, nitration, sulfonation, and the Friedel–Crafts reaction . By taking advantage of a Lewis acid as the catalyst, the reaction could work on the electron-neutral aromatic ring.…”

Section: Principlementioning

confidence: 99%

Two-Step Synthesis of 4-Hydroxy-3,5-dimethylphenyl Benzoate: Undergraduate Organic Laboratory of Electrophilic Aromatic Substitution and Nucleophilic Aromatic Substitution

Han,

Qin,

Wang

et al. 2024

J. Chem. Educ.

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Organic Chemistry and Synthesis Rely More and More upon Catalysts

Vogel

Houk

2022

Catalysts

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A few months before the COVID-19 pandemic, Pierre Vogel and Kendall N. Houk published with a new textbook Wiley-VCH, “Organic Chemistry: Theory, Reactivity, and Mechanisms in Modern Synthesis”, with a foreword from the late Roberts H. Grubbs. The book demonstrates how catalytic processes dominate all fields of modern organic chemistry and synthesis, and how invention combines thermodynamics, kinetics, spectroscopy, quantum mechanics, and thermochemical data libraries. Here, the authors present a few case studies that should be of interest to teachers, practitioners of organic and organometallic chemistry, and the engineers of molecules. The Vogel–Houk book is both textbook and reference manual; it provides a modern way to think about chemical reactivity and a powerful toolbox to inventors of new reactions and new procedures.

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S<sub>E</sub>Ar Mechanism of the Products of 1,2-Dimethoxybenzene and a Captodative Olefin: A Theoretical Approach

Santana-García,

Aviña-Verduzco,

Herrera-Bucio

et al. 2024

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Electrophilic Aromatic Substitution

Cited by 3 publications

References 135 publications

Two-Step Synthesis of 4-Hydroxy-3,5-dimethylphenyl Benzoate: Undergraduate Organic Laboratory of Electrophilic Aromatic Substitution and Nucleophilic Aromatic Substitution

Two-Step Synthesis of 4-Hydroxy-3,5-dimethylphenyl Benzoate: Undergraduate Organic Laboratory of Electrophilic Aromatic Substitution and Nucleophilic Aromatic Substitution

Organic Chemistry and Synthesis Rely More and More upon Catalysts

S<sub>E</sub>Ar Mechanism of the Products of 1,2-Dimethoxybenzene and a Captodative Olefin: A Theoretical Approach

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