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21. Draw the mechanism of each of the following solvolysis reactions: EIOH Br (solvolysis) но (solvolysis) CI

21. Draw the mechanism of each of the following solvolysis reactions: EIOH Br (solvolysis) но (solvolysis) CI

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
Section: Chapter Questions
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**Transcription and Explanation for Educational Website:** **Question 21:** Draw the mechanism of each of the following solvolysis reactions: **Reaction 1:** - Reactant: A bromide compound with a benzene ring and an isopropyl group attached. - Solvent: Ethanol (EtOH) - Product: An ether compound with the same carbon skeleton, where the bromine atom is replaced by an ethoxy group. **Reaction 2:** - Reactant: A chloride compound with a benzene ring and a straight-chain alkyl group. - Solvent: Water (H₂O) - Product: An alcohol compound with the same carbon skeleton, where the chlorine atom is replaced by a hydroxyl group. **Explanation of Mechanisms:** - **Solvolysis Reaction:** This type of reaction involves the substitution of a leaving group (like bromine or chlorine) by a solvent molecule. These reactions often proceed via an SN1 mechanism, which involves two main steps: 1. **Formation of a Carbocation:** The leaving group (Br or Cl) departs, creating a positively charged carbon center (carbocation). 2. **Nucleophilic Attack:** The solvent molecule (EtOH or H₂O) attacks the carbocation, forming a new bond and resulting in the substitution product. - **Structure Details:** - *Reactant 1* involves the solvolysis of a bromine atom using ethanol as a solvent, resulting in an ether. - *Reactant 2* involves the solvolysis of a chlorine atom using water as a solvent, resulting in an alcohol. Each reaction demonstrates a typical solvolysis process with the substitution of halogen atoms by solvent molecules forming new organic compounds.
Transcribed Image Text:**Transcription and Explanation for Educational Website:** **Question 21:** Draw the mechanism of each of the following solvolysis reactions: **Reaction 1:** - Reactant: A bromide compound with a benzene ring and an isopropyl group attached. - Solvent: Ethanol (EtOH) - Product: An ether compound with the same carbon skeleton, where the bromine atom is replaced by an ethoxy group. **Reaction 2:** - Reactant: A chloride compound with a benzene ring and a straight-chain alkyl group. - Solvent: Water (H₂O) - Product: An alcohol compound with the same carbon skeleton, where the chlorine atom is replaced by a hydroxyl group. **Explanation of Mechanisms:** - **Solvolysis Reaction:** This type of reaction involves the substitution of a leaving group (like bromine or chlorine) by a solvent molecule. These reactions often proceed via an SN1 mechanism, which involves two main steps: 1. **Formation of a Carbocation:** The leaving group (Br or Cl) departs, creating a positively charged carbon center (carbocation). 2. **Nucleophilic Attack:** The solvent molecule (EtOH or H₂O) attacks the carbocation, forming a new bond and resulting in the substitution product. - **Structure Details:** - *Reactant 1* involves the solvolysis of a bromine atom using ethanol as a solvent, resulting in an ether. - *Reactant 2* involves the solvolysis of a chlorine atom using water as a solvent, resulting in an alcohol. Each reaction demonstrates a typical solvolysis process with the substitution of halogen atoms by solvent molecules forming new organic compounds.
**Carbocation Rearrangement with Proton Transfer Process** Here is an example of an S<sub>N</sub>1 process that is accompanied by all three additional steps: - **Proton Transfer:** The hydroxyl group (\(-OH\)) is protonated by \(H_3O^+/MeOH\), transforming it into a better leaving group. - **Loss of Leaving Group:** The \(-H_2O\) departs, forming a secondary carbocation. - **Carbocation Rearrangement:** The secondary carbocation undergoes rearrangement to form a more stable tertiary carbocation. - **Proton Transfer:** - **Nucleophilic Attack:** Methanol (\(MeOH\)) attacks the carbocation, leading to a protonated ether. - **Proton Transfer:** Deprotonation occurs, forming the ether product. **Energy Diagram for Carbocation Rearrangement with Proton Transfer** - **Potential Energy vs. Reaction Coordinate:** - The diagram showcases the energy changes throughout the reaction stages. - Starts with the initial reactant involving a proton transfer step. - Peaks at the loss of the leaving group, forming a secondary carbocation. - Proceeds to carbocation rearrangement reaching another energy peak. - Followed by nucleophilic attack decreasing energy. - Ends with a proton transfer, forming a stable product. Each stage indicates distinct energy profiles for proton transfer, loss of leaving group, carbocation rearrangement, nucleophilic attack, and a final proton transfer.
Transcribed Image Text:**Carbocation Rearrangement with Proton Transfer Process** Here is an example of an S<sub>N</sub>1 process that is accompanied by all three additional steps: - **Proton Transfer:** The hydroxyl group (\(-OH\)) is protonated by \(H_3O^+/MeOH\), transforming it into a better leaving group. - **Loss of Leaving Group:** The \(-H_2O\) departs, forming a secondary carbocation. - **Carbocation Rearrangement:** The secondary carbocation undergoes rearrangement to form a more stable tertiary carbocation. - **Proton Transfer:** - **Nucleophilic Attack:** Methanol (\(MeOH\)) attacks the carbocation, leading to a protonated ether. - **Proton Transfer:** Deprotonation occurs, forming the ether product. **Energy Diagram for Carbocation Rearrangement with Proton Transfer** - **Potential Energy vs. Reaction Coordinate:** - The diagram showcases the energy changes throughout the reaction stages. - Starts with the initial reactant involving a proton transfer step. - Peaks at the loss of the leaving group, forming a secondary carbocation. - Proceeds to carbocation rearrangement reaching another energy peak. - Followed by nucleophilic attack decreasing energy. - Ends with a proton transfer, forming a stable product. Each stage indicates distinct energy profiles for proton transfer, loss of leaving group, carbocation rearrangement, nucleophilic attack, and a final proton transfer.
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