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(a) E1 (b) E2 +- ₹ H2O OCH 3

(a) E1 (b) E2 +- ₹ H2O OCH 3

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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Provide a mechanism which explains the following conversions. Include all intermediates and watch you arrows and charges
**Elimination Reactions** In organic chemistry, elimination reactions are a class of reactions where elements are removed from a molecule, often resulting in the formation of a double bond. Two common types of elimination reactions are E1 and E2 reactions, detailed below with examples. --- **(a) E1 Reaction** In an E1 reaction, the substrate undergoes a two-step mechanism: - **Step 1:** Loss of the leaving group (a chloride ion, Cl⁻), forming a carbocation intermediate. - **Step 2:** Deprotonation occurs, leading to the formation of an alkene. *Example Reaction:* - The starting compound is a secondary alkyl chloride, which in the presence of water (H₂O) undergoes dehydration to form an alkene, typically a more substituted and stable double bond. **Mechanism:** 1. The Cl group leaves, forming a carbocation. 2. A hydrogen atom is removed from an adjacent carbon, resulting in the formation of a double bond. **Diagram Explanation:** - The diagram shows the transformation from an alkyl chloride to an alkene, with H₂O as a solvent. --- **(b) E2 Reaction** In an E2 reaction, the substrate undergoes a one-step mechanism: - **Simultaneous Event:** The leaving group (iodide, I⁻) and a hydrogen atom are removed simultaneously, forming a double bond. *Example Reaction:* - The starting compound is a primary alkyl iodide, and in the presence of a strong base (methoxide ion, ⁻OCH₃), an alkene is formed. **Mechanism:** 1. The I group leaves as the ⁻OCH₃ base abstracts a hydrogen. 2. A new double bond forms between the two previously single-bonded carbon atoms. **Diagram Explanation:** - The diagram represents the direct conversion of an alkyl iodide to an alkene, facilitated by a strong base. --- **Conclusion** Both E1 and E2 reactions are crucial in synthetic organic chemistry, serving as pathways to synthesize alkenes from alkyl halides. The choice between E1 and E2 depends on factors such as substrate structure, solvent, and the presence of a base or acid.
Transcribed Image Text:**Elimination Reactions** In organic chemistry, elimination reactions are a class of reactions where elements are removed from a molecule, often resulting in the formation of a double bond. Two common types of elimination reactions are E1 and E2 reactions, detailed below with examples. --- **(a) E1 Reaction** In an E1 reaction, the substrate undergoes a two-step mechanism: - **Step 1:** Loss of the leaving group (a chloride ion, Cl⁻), forming a carbocation intermediate. - **Step 2:** Deprotonation occurs, leading to the formation of an alkene. *Example Reaction:* - The starting compound is a secondary alkyl chloride, which in the presence of water (H₂O) undergoes dehydration to form an alkene, typically a more substituted and stable double bond. **Mechanism:** 1. The Cl group leaves, forming a carbocation. 2. A hydrogen atom is removed from an adjacent carbon, resulting in the formation of a double bond. **Diagram Explanation:** - The diagram shows the transformation from an alkyl chloride to an alkene, with H₂O as a solvent. --- **(b) E2 Reaction** In an E2 reaction, the substrate undergoes a one-step mechanism: - **Simultaneous Event:** The leaving group (iodide, I⁻) and a hydrogen atom are removed simultaneously, forming a double bond. *Example Reaction:* - The starting compound is a primary alkyl iodide, and in the presence of a strong base (methoxide ion, ⁻OCH₃), an alkene is formed. **Mechanism:** 1. The I group leaves as the ⁻OCH₃ base abstracts a hydrogen. 2. A new double bond forms between the two previously single-bonded carbon atoms. **Diagram Explanation:** - The diagram represents the direct conversion of an alkyl iodide to an alkene, facilitated by a strong base. --- **Conclusion** Both E1 and E2 reactions are crucial in synthetic organic chemistry, serving as pathways to synthesize alkenes from alkyl halides. The choice between E1 and E2 depends on factors such as substrate structure, solvent, and the presence of a base or acid.
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