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Classify the following substituents according to whether they are electron donors or electron acceptors relative to hydrogen by the resonance and the inductive mechanisms. a = acceptor d = donor n = no effect 1. 2. d 3. a CH3 -Se: Inductive effect a CH3 :0: || O-CCH₂CH₂CCH3 :0: :0: || -CH=CH-C-ÖCH3 . Resonance effect d Inductive effect a Inductive effect a Resonance effect Resonance effect

Classify the following substituents according to whether they are electron donors or electron acceptors relative to hydrogen by the resonance and the inductive mechanisms. a = acceptor d = donor n = no effect 1. 2. d 3. a CH3 -Se: Inductive effect a CH3 :0: || O-CCH₂CH₂CCH3 :0: :0: || -CH=CH-C-ÖCH3 . Resonance effect d Inductive effect a Inductive effect a Resonance effect Resonance effect

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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**Classify Substituents as Electron Donors or Acceptors** Evaluate the following substituents to determine if they act as electron donors or acceptors relative to hydrogen based on resonance and inductive effects. Use these symbols: - \( a \) = acceptor - \( d \) = donor - \( n \) = no effect 1. **Substituent: \(-\text{Se}^+\) with \(\text{CH}_3\) groups** - **Inductive Effect:** \( a \) ✓ - **Resonance Effect:** \( d \) ✕ ![Molecular structure](substituent-structure-1.png) 2. **Substituent: \(\text{O}-\text{CCH}_2\text{CH}_2\text{CCH}_3\)** - **Inductive Effect:** \( a \) ✓ - **Resonance Effect:** \( d \) ✓ ![Molecular structure](substituent-structure-2.png) 3. **Substituent: \(-\text{CH}=\text{CH}-\text{C}=\text{OCH}_3\)** - **Inductive Effect:** \( a \) ✓ - **Resonance Effect:** \( a \) ✓ ![Molecular structure](substituent-structure-3.png) **Explanation:** - The inductive effect describes the electron-withdrawing or electron-donating ability of substituents through sigma bonds. - The resonance effect involves the delocalization of electrons through pi bonds, affecting the electron density at various positions. Understanding these effects is essential in predicting the behavior of molecules in reactions, such as electrophilic aromatic substitutions and nucleophilic substitutions.
Transcribed Image Text:**Classify Substituents as Electron Donors or Acceptors** Evaluate the following substituents to determine if they act as electron donors or acceptors relative to hydrogen based on resonance and inductive effects. Use these symbols: - \( a \) = acceptor - \( d \) = donor - \( n \) = no effect 1. **Substituent: \(-\text{Se}^+\) with \(\text{CH}_3\) groups** - **Inductive Effect:** \( a \) ✓ - **Resonance Effect:** \( d \) ✕ ![Molecular structure](substituent-structure-1.png) 2. **Substituent: \(\text{O}-\text{CCH}_2\text{CH}_2\text{CCH}_3\)** - **Inductive Effect:** \( a \) ✓ - **Resonance Effect:** \( d \) ✓ ![Molecular structure](substituent-structure-2.png) 3. **Substituent: \(-\text{CH}=\text{CH}-\text{C}=\text{OCH}_3\)** - **Inductive Effect:** \( a \) ✓ - **Resonance Effect:** \( a \) ✓ ![Molecular structure](substituent-structure-3.png) **Explanation:** - The inductive effect describes the electron-withdrawing or electron-donating ability of substituents through sigma bonds. - The resonance effect involves the delocalization of electrons through pi bonds, affecting the electron density at various positions. Understanding these effects is essential in predicting the behavior of molecules in reactions, such as electrophilic aromatic substitutions and nucleophilic substitutions.
Electrophilic aromatic substitution is a two-step process. In the first step, an electrophile, here generically shown as Y⁺, reacts with the aromatic ring to form a resonance-stabilized carbocation intermediate. In the second step, loss of a proton from the site of attack restores aromaticity to the ring and completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. **Arrow-pushing Instructions** Below the text, there is a toolbar image displaying different arrow types used in electron-pushing mechanisms. **Diagram Explanation:** 1. **First Diagram**: A benzene ring is shown reacting with an electrophile (Y⁺) indicated by an arrow pointing to the benzene. 2. **Second Diagram**: Shows the benzene ring with a substituent Y attached, and a hydrogen ion (H⁺) is shown as a byproduct. 3. **Third Diagram**: Displays a benzene ring with a positively charged site where the electrophile (Y) is attached, alongside a hydrogen atom, indicating where the substitution has occurred.
Transcribed Image Text:Electrophilic aromatic substitution is a two-step process. In the first step, an electrophile, here generically shown as Y⁺, reacts with the aromatic ring to form a resonance-stabilized carbocation intermediate. In the second step, loss of a proton from the site of attack restores aromaticity to the ring and completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. **Arrow-pushing Instructions** Below the text, there is a toolbar image displaying different arrow types used in electron-pushing mechanisms. **Diagram Explanation:** 1. **First Diagram**: A benzene ring is shown reacting with an electrophile (Y⁺) indicated by an arrow pointing to the benzene. 2. **Second Diagram**: Shows the benzene ring with a substituent Y attached, and a hydrogen ion (H⁺) is shown as a byproduct. 3. **Third Diagram**: Displays a benzene ring with a positively charged site where the electrophile (Y) is attached, alongside a hydrogen atom, indicating where the substitution has occurred.
Expert Solution
Step 1

Se (Selenium) is an element in group 16 (oxygen family). A positive charge on Se decreases the electron density on it , thereby increasing the electron-withdrawing nature of the group.

This means its resonance effect will be acceptor.

Resonenece effect    a

All other answers are correct

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