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What are the products of the following reactions if they proceed via the SN1 mechanism? CH2CH3 %3D НО + Br CH3 (b) trans-1-chloro-2-methylcyclohexane CH30

What are the products of the following reactions if they proceed via the SN1 mechanism? CH2CH3 %3D НО + Br CH3 (b) trans-1-chloro-2-methylcyclohexane CH30

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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What are the products of the following reactions if they proceed via the SN1 mechanism?

**Question:** What are the products of the following reactions if they proceed via the SN1 mechanism? **Reactions:** (a) - **Reactants:** - Tertiary butyl bromide (structural representation: CH₂CH₃ on the left, H above, CH₃ on the right, Br attached to the central carbon) - Hydroxide ion (OH⁻) - **Expected Products:** (b) - **Reactants:** - Trans-1-chloro-2-methylcyclohexane - Methoxide ion (CH₃O⁻) - **Expected Products:** **Explanations:** - **Reaction (a):** The tertiary butyl bromide undergoes an SN1 reaction. In such a mechanism, the bromide ion (Br⁻) leaves first, forming a tertiary carbocation, which is then attacked by the hydroxide ion (OH⁻) leading to the formation of an alcohol. - **Reaction (b):** The trans-1-chloro-2-methylcyclohexane undergoes an SN1 reaction where the chloride ion (Cl⁻) departs to form a carbocation. The methoxide ion (CH₃O⁻) then attacks the carbocation, resulting in the formation of an ether. **Note:** In SN1 reactions, the rate is determined by the formation of the carbocation, making it a two-step process with the leaving group departing before the nucleophile attacks.
Transcribed Image Text:**Question:** What are the products of the following reactions if they proceed via the SN1 mechanism? **Reactions:** (a) - **Reactants:** - Tertiary butyl bromide (structural representation: CH₂CH₃ on the left, H above, CH₃ on the right, Br attached to the central carbon) - Hydroxide ion (OH⁻) - **Expected Products:** (b) - **Reactants:** - Trans-1-chloro-2-methylcyclohexane - Methoxide ion (CH₃O⁻) - **Expected Products:** **Explanations:** - **Reaction (a):** The tertiary butyl bromide undergoes an SN1 reaction. In such a mechanism, the bromide ion (Br⁻) leaves first, forming a tertiary carbocation, which is then attacked by the hydroxide ion (OH⁻) leading to the formation of an alcohol. - **Reaction (b):** The trans-1-chloro-2-methylcyclohexane undergoes an SN1 reaction where the chloride ion (Cl⁻) departs to form a carbocation. The methoxide ion (CH₃O⁻) then attacks the carbocation, resulting in the formation of an ether. **Note:** In SN1 reactions, the rate is determined by the formation of the carbocation, making it a two-step process with the leaving group departing before the nucleophile attacks.
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