Aromatic Substitution

AROMATIC SUBSTITUTION REACTIONS

AROMATIC SUBSTITUTION REACTIONS . 36 kcal/mol resonance. “Double” bonds in a benzene ring do not react like those in an alkene. easier . E +. Instead of addition reactions, benzene rings give substitution reactions (resonance preserved). More powerful electrophiles

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Electrophilic Aromatic Substitution (Bromination of Toluene)

Electrophilic Aromatic Substitution (Bromination of Toluene). Demonstration of the effect of a monosubstituted electron donar group (ring activator) on subsequent substitution of other groups on the Benzene ring References Slayden Lab Manual – p. 61 – 65 Pavia Lab Text – p. 347 – 349

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Aromatic Substitution

Aromatic Substitution. Chapter 22. Reading Assignment. Sections 22.0 through 22.2 Sections 22.4 through 22.9 Sections 22.10 through 22.12 Section 22.17 Section 22.18 (chapter summary) Problems. Assigned Problems. In-text problems 22-1 through 22-2 22-4 through 22-13

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Electrophilic Aromatic Substitution

Synthesis of Benzene Derivatives: Electrophilic Aromatic Substitution. 15-8. Benzene undergoes substitution reactions with electrophiles.Electrophiles attack benzene by substituting for a hydrogen atom, not addition to the ring.. Under the conditions of this type of reaction, ordinary non-aromatic conjugated polyenes would polymerize rapidly..

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Aromatic Substitution

Aromatic Substitution . Chapter 22. Sections to skip!!. Skip sections 22.1 (most), 22.3, 22.4, and 2.13 through 22.15 Keep 22.16 (review from c. 351, for some of you) Keep 22.17. Problems. In text: 4 - 6 8 - 13 20 - 29 End of Chapter: 1 - 5 9 - 13 . Sect. 22.1 Nomenclature.

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Electrophilic Aromatic Substitution

Electrophilic Aromatic Substitution. Part 2. Meta Directors. A. Highly Electron Withdrawing Groups. -CF 3. B. Atom in a Multiple Bond to a More Electronegative Atom. CF 3. CF 3. +. +. H 3 C. F 3 C. C. C. H 2 SO 4. NO 2. +. HNO 3. META DIRECTORS. NET RXN.

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Chemistry of Benzene: Electrophilic Aromatic Substitution

Chapter 16. Chemistry of Benzene: Electrophilic Aromatic Substitution. Introduction. Electrophilic aromatic substitution is the most common reaction of aromatic compounds It replaces a proton ( H + ) on an aromatic ring with another electrophile ( E + )

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Chapter 4. AROMATIC ELECTROPHILIC SUBSTITUTION REACTIONS

4.1. Introduction. Definition: AES = Replacement of one of the H on an aromatic ring by an electrophileSubstrates = Aromatic rings. Reaction sites: C=C bonds on the ring. Characteristic of rxn sites: presence of pi-electrons which attract electrophiles Reagents: electrophiles seeking to bind with

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Chapter 18 Electrophilic Aromatic Substitution

Chapter 18 Electrophilic Aromatic Substitution. 18.1. Electrophilic Aromatic Substitution. Background. The characteristic reaction of benzene is electrophilic aromatic substitution —a hydrogen atom is replaced by an electrophile. 18.1. Electrophilic Aromatic Substitution.

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Aromatic Substitution

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Electrophilic Aromatic substitution (EAS) Reactions Bromination

CHEM 2211 Organic Chemistry I: Chapter 8 Summary of Reactions Know these!!!!! Slides 2-7 show the EAS reactions Slides 8-10 show the side chain reactions. Electrophilic Aromatic substitution (EAS) Reactions Bromination. Note: All species shown underneath the arrows

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Electrophilic Aromatic Substitution

Author: Sukumar Honkote Chemistry Department, IIT Bombay. Electrophilic Aromatic Substitution. Electrophilic Aromatic Substitution involves the attack on the electrophile by the ∏ electrons of the aromatic ring and replacing one of the hydrogen molecules on the ring.

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Electrophilic aromatic substitution

Electrophilic aromatic substitution. Substitution?. The characteristic reactions of benzene involve substitution in which the resonance stabilized ring system is maintained:. Reactivity. - an electron source, benzene reacts with electron deficient reagents - electrophilic reagents.

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Substituent Effects: Electrophilic Aromatic Substitution

Substituent Effects: Electrophilic Aromatic Substitution. Substituents that are capable of donating electrons into the benzene ring will stabilize both the carbocation intermediate and the transition state leading to its formation Increases the rate of electrophilic aromatic substitution

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Electrophilic Aromatic Substitution (EAS)Reactions

Electrophilic Aromatic Substitution (EAS)Reactions. Overall reaction. General Mechanism for Electrophilic Aromatic Substitution. Summary of ERS Reactions. Halogenation of Benzene. General Equation:. Electrophile = X +. EX:. Nitration of Benzene. General Equation:.

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Electrophilic Aromatic Substitution (Bromination of Toluene)

Electrophilic Aromatic Substitution (Bromination of Toluene). Demonstration of the Effect of an Electron Donar Group (ring activator) on a monosubstituted Benzene on subsequent substitution of other groups References Slayden Lab Manual – p. 75-76

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Chapter 17 Aromatic Substitution Reactions

Chapter 17 Aromatic Substitution Reactions. 17.1 Mechanism for Electricphilic Aromatic Substitution. Arenium ion resonance stabilization. Example 1. Example 2. Example 2. Mechanism of the nitration of benzene. Addition reaction vs. Electrophilic aromatic substitution. Stability.

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Electrophilic Aromatic Substitution

Electrophilic Aromatic Substitution. Reaction Pattern Variation o,p vs. m. Electron Withdrawing Substituents. Electron Withdrawing Substituents. Electron Withdrawing Substituents. Electron Withdrawing Substituents. Electron Withdrawing Substituents. Electron Withdrawing Substituents.

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Electrophilic Aromatic Substitution

Electrophilic Aromatic Substitution. Activating and Directing effects of substituents already on the ring. Products of Nitration. 1 hr. 48 hr. 0.0003 hr. Mechanism of Electrophilic Aromatic Substitution. With a substituent group G.

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Aromatic Substitution

Aromatic Substitution. Chapter 22. Sections to skip!!. Skip sections 22.1 (most), 22.3, 22.4, and 2.13 through 22.15 Keep 22.16 (review from c. 351, for some of you) Keep 22.17. Problems. In text: 4 - 6 8 - 13 20 - 29 End of Chapter: 1 - 5 9 - 13 . Sect. 22.1 Nomenclature.

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Benzene and Electrophilic Aromatic Substitution

Benzene and Electrophilic Aromatic Substitution. C 6 H 5 CH 3. C 6 H 5 C 2 H 5. Aromatic Hydrocarbons (Arenes). Simplest member : Benzene, C 6 H 6 Characteristic aroma Alkylbenzene, C n+6 H 2n+6 E.g. Aromatic Hydrocarbons (Arenes). Generally less dense than water

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Electrophilic Aromatic Substitution

Electrophilic Aromatic Substitution. Activating and Directing effects of substituents already on the ring. Products of Nitration. 1 hr. 48 hr. 0.0003 hr. Mechanism of Electrophilic Aromatic Substitution. With a substituent group G.

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