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Predict the most likely mechanism for the reaction shown below. CI CH₂ CH3 H₂O A

Predict the most likely mechanism for the reaction shown below. CI CH₂ CH3 H₂O A

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter13: Substitution
Section: Chapter Questions
Problem 2E
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### Reaction Mechanism Prediction **Task:** Predict the most likely mechanism for the reaction shown below. **Reaction Overview:** A cyclohexane ring with a chlorine substituent (Cl) and two methyl groups (CH₃) in a 1,3-dimethyl arrangement undergoes reaction in the presence of water (H₂O) and heat (Δ). **Diagram:** - The starting molecule is a 1-chloro-3,3-dimethyl-cyclohexane. - The chlorine atom is positioned at the first carbon of the cyclohexane ring. - Adjacent to the chlorine, there are two methyl groups attached to the third carbon of the ring. - The reaction conditions are represented by H₂O and the symbol Δ (which represents heat). **Explanation:** Given the presence of the chlorine substituent and the reaction conditions (H₂O and heat), the most likely mechanism for this reaction is the nucleophilic substitution reaction, specifically an Sₙ1 mechanism due to the stabilization of the carbocation by the inductive and hyperconjugative effects of the methyl groups. ### Expected Sₙ1 Reaction Steps: 1. **Formation of a Carbocation:** The chlorine leaving group departs, forming a tertiary carbocation (3°), which is stabilized by the adjacent methyl groups. 2. **Nucleophilic Attack:** Water (H₂O) acts as a nucleophile, attacking the carbocation, leading to the formation of a protonated alcohol. 3. **Deprotonation:** The protonated alcohol loses a proton (H⁺), forming the final alcohol product. **Key Points:** - **Sₙ1 Mechanism** involves a two-step process: ionization to form a carbocation followed by nucleophilic attack. - **Stabilization of the Carbocation**: The two methyl groups donate electron density via hyperconjugation, stabilizing the positive charge. - **Heat** (Δ) provides the necessary energy to overcome the activation barrier for the leaving group to depart. This Sₙ1 mechanism is favored in the presence of a strong polar solvent like water and the ability to stabilize the intermediate carbocation.
Transcribed Image Text:### Reaction Mechanism Prediction **Task:** Predict the most likely mechanism for the reaction shown below. **Reaction Overview:** A cyclohexane ring with a chlorine substituent (Cl) and two methyl groups (CH₃) in a 1,3-dimethyl arrangement undergoes reaction in the presence of water (H₂O) and heat (Δ). **Diagram:** - The starting molecule is a 1-chloro-3,3-dimethyl-cyclohexane. - The chlorine atom is positioned at the first carbon of the cyclohexane ring. - Adjacent to the chlorine, there are two methyl groups attached to the third carbon of the ring. - The reaction conditions are represented by H₂O and the symbol Δ (which represents heat). **Explanation:** Given the presence of the chlorine substituent and the reaction conditions (H₂O and heat), the most likely mechanism for this reaction is the nucleophilic substitution reaction, specifically an Sₙ1 mechanism due to the stabilization of the carbocation by the inductive and hyperconjugative effects of the methyl groups. ### Expected Sₙ1 Reaction Steps: 1. **Formation of a Carbocation:** The chlorine leaving group departs, forming a tertiary carbocation (3°), which is stabilized by the adjacent methyl groups. 2. **Nucleophilic Attack:** Water (H₂O) acts as a nucleophile, attacking the carbocation, leading to the formation of a protonated alcohol. 3. **Deprotonation:** The protonated alcohol loses a proton (H⁺), forming the final alcohol product. **Key Points:** - **Sₙ1 Mechanism** involves a two-step process: ionization to form a carbocation followed by nucleophilic attack. - **Stabilization of the Carbocation**: The two methyl groups donate electron density via hyperconjugation, stabilizing the positive charge. - **Heat** (Δ) provides the necessary energy to overcome the activation barrier for the leaving group to depart. This Sₙ1 mechanism is favored in the presence of a strong polar solvent like water and the ability to stabilize the intermediate carbocation.
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