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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5:43 minutes

Problem 46c

Textbook Question

What products will be obtained from the E1 reaction of the alkyl halides in [PROBLEM 9-45]?
c.

Verified step by step guidance

Identify the structure of the alkyl halide provided in the problem. For an E1 reaction, the alkyl halide should typically be a secondary or tertiary halide, as these are more prone to carbocation formation.

Determine the first step of the E1 mechanism: the leaving group departs, forming a carbocation intermediate. Write the structure of the carbocation and ensure it is stable (e.g., tertiary carbocations are more stable than secondary).

Check for the possibility of carbocation rearrangement. If a more stable carbocation can form via hydride or alkyl shift, draw the rearranged structure.

Identify the β-hydrogens (hydrogens on carbons adjacent to the carbocation). These are the hydrogens that can be eliminated to form a double bond. Write the possible elimination pathways.

Draw the final products by removing a β-hydrogen and forming a double bond between the carbocation carbon and the β-carbon. Consider Zaitsev's rule, which states that the more substituted alkene is typically the major product.

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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 elimination of a proton to form a double bond. The rate of the reaction depends only on the concentration of the alkyl halide, making it unimolecular.

Carbocation Stability

Carbocation stability is crucial in E1 reactions, as more stable carbocations (tertiary > secondary > primary) are formed preferentially. The stability is influenced by factors such as hyperconjugation and inductive effects from adjacent alkyl groups. The more stable the carbocation, the more likely the E1 reaction will proceed.

Regioselectivity and Stereochemistry

In E1 reactions, regioselectivity refers to the preference for forming certain alkene products over others, often determined by the stability of the resulting double bond. Additionally, stereochemistry plays a role, as the elimination can lead to different geometric isomers (cis/trans) depending on the orientation of the substituents around the double bond formed.

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