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1.) Propose the mechanism for the reaction below. Please draw arrows for the mechanism. OH NaBr H₂SO4, H₂O b.) Is it likely to go via Sn1 or Sn2? Explain.

1.) Propose the mechanism for the reaction below. Please draw arrows for the mechanism. OH NaBr H₂SO4, H₂O b.) Is it likely to go via Sn1 or Sn2? Explain.

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
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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### Reaction Mechanism Exercise **Question 1: Propose the mechanism for the reaction below. Please draw arrows for the mechanism.** #### Reaction Details: - **Reactant:** Primary alcohol - **Reagents:** NaBr, H₂SO₄, H₂O The structure represents a linear chain with an alcohol group (–OH) attached to one of the carbon atoms. **Steps for Mechanism Proposal:** - Protonation of the alcohol group by H₂SO₄ to form water (a good leaving group). - Formation of a carbocation intermediate. - Nucleophilic attack by Br⁻ provided by NaBr. **Question 1b: Is it likely to go via Sn1 or Sn2? Explain.** **Explanation:** - **Sn1 Reaction** involves a two-step mechanism with the formation of a carbocation intermediate. This is more common in tertiary alcohols due to carbocation stability. - **Sn2 Reaction** involves a one-step mechanism where the nucleophile attacks the substrate as the leaving group departs, often seen in primary alcohols. Since the alcohol in this reaction is primary, it is more likely to proceed via an Sn2 mechanism, where the bromide ion attacks the carbon attached to the leaving group as water departs. ### Graphs or Diagrams: Diagrams show reaction structures or pathways of the proposed mechanism typically include: - Initial alcohol structure with protonation step. - Intermediate carbocation (if Sn1 considered). - Final substitution product with Br⁻ replacing hydroxyl group. This explanation covers the conceptual understanding of the reaction mechanism and the likely pathway (Sn1 or Sn2) the reaction would follow.
Transcribed Image Text:### Reaction Mechanism Exercise **Question 1: Propose the mechanism for the reaction below. Please draw arrows for the mechanism.** #### Reaction Details: - **Reactant:** Primary alcohol - **Reagents:** NaBr, H₂SO₄, H₂O The structure represents a linear chain with an alcohol group (–OH) attached to one of the carbon atoms. **Steps for Mechanism Proposal:** - Protonation of the alcohol group by H₂SO₄ to form water (a good leaving group). - Formation of a carbocation intermediate. - Nucleophilic attack by Br⁻ provided by NaBr. **Question 1b: Is it likely to go via Sn1 or Sn2? Explain.** **Explanation:** - **Sn1 Reaction** involves a two-step mechanism with the formation of a carbocation intermediate. This is more common in tertiary alcohols due to carbocation stability. - **Sn2 Reaction** involves a one-step mechanism where the nucleophile attacks the substrate as the leaving group departs, often seen in primary alcohols. Since the alcohol in this reaction is primary, it is more likely to proceed via an Sn2 mechanism, where the bromide ion attacks the carbon attached to the leaving group as water departs. ### Graphs or Diagrams: Diagrams show reaction structures or pathways of the proposed mechanism typically include: - Initial alcohol structure with protonation step. - Intermediate carbocation (if Sn1 considered). - Final substitution product with Br⁻ replacing hydroxyl group. This explanation covers the conceptual understanding of the reaction mechanism and the likely pathway (Sn1 or Sn2) the reaction would follow.
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