Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

8. Elimination Reactions

E1 Reaction

Organic Chemistry

8. Elimination Reactions

E1 Reaction

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Problem 38c

Textbook Question

Practice your electron-pushing skills by drawing a mechanism for the following E1 reactions.
(c)

Verified step by step guidance

Step 1: Identify the reaction type. This is an E1 elimination reaction, which involves two steps: the formation of a carbocation intermediate and the elimination of a proton to form a double bond.

Step 2: Analyze the substrate. The starting molecule contains a tertiary alkyl chloride group. Tertiary carbocations are highly stable due to hyperconjugation and inductive effects, making this substrate suitable for an E1 mechanism.

Step 3: First step of the mechanism - Formation of the carbocation. The chlorine atom (Cl) leaves as a chloride ion (Cl⁻), resulting in the formation of a tertiary carbocation at the bridgehead position. This step is facilitated by the polar protic solvent (H₂O), which stabilizes the carbocation.

Step 4: Second step of the mechanism - Proton elimination. A hydrogen atom from a β-carbon (adjacent to the carbocation) is removed by water acting as a base. The electrons from the C-H bond move to form a π bond, resulting in the formation of the double bond in the product.

Step 5: Verify the product structure. The final product is a bicyclic alkene with a double bond in the ring system, as shown in the image. Ensure the double bond is correctly positioned based on the most stable carbocation and elimination pathway.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

E1 Reaction Mechanism

The E1 (unimolecular elimination) reaction is a two-step mechanism where the first step involves the formation of a carbocation intermediate after the leaving group departs. This is followed by the deprotonation of a neighboring carbon to form a double bond. Understanding this mechanism is crucial for predicting the products and the stability of intermediates involved.

Carbocation Stability

Carbocation stability is a key factor in E1 reactions, as more stable carbocations will form more readily. Stability is influenced by factors such as the degree of substitution (tertiary > secondary > primary) and resonance effects. Recognizing the stability of potential carbocation intermediates helps in determining the feasibility and rate of the E1 reaction.

Electron-Pushing Curved Arrows

Electron-pushing curved arrows are a notation used to illustrate the movement of electron pairs during chemical reactions. In the context of E1 mechanisms, these arrows help depict the departure of the leaving group and the subsequent formation of the double bond. Mastery of this notation is essential for accurately representing reaction mechanisms and understanding the flow of electrons.

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