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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4:32 minutes

Problem 84c

Textbook Question

Draw the major product obtained when an alkyl halide in [PROBLEM 9-83] undergoes an E1 reaction.
c.

Verified step by step guidance

Step 1: Identify the alkyl halide structure provided in the image. The molecule is a cyclohexyl bromide, where bromine is attached to a cyclohexane ring.

Step 2: Understand the E1 reaction mechanism. E1 reactions proceed via a two-step process: (1) the leaving group (Br) departs, forming a carbocation intermediate, and (2) a proton is removed from a β-carbon, leading to the formation of a double bond.

Step 3: Determine the stability of the carbocation intermediate. When bromine leaves, a cyclohexyl carbocation is formed. This carbocation is relatively stable due to the ring structure and hyperconjugation effects.

Step 4: Identify the β-hydrogens available for elimination. In the cyclohexyl carbocation, hydrogens on the carbons adjacent to the carbocation (β-carbons) are potential candidates for elimination. Removing one of these hydrogens will result in the formation of a double bond.

Step 5: Predict the major product. The major product will be the most stable alkene formed by elimination. In this case, the double bond will likely form between the carbocation carbon and one of the β-carbons, resulting in a cyclohexene structure.

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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 reaction mechanism is a type of elimination reaction that involves two steps: the formation of a carbocation intermediate followed by the loss of a proton to form a double bond. This mechanism typically occurs with tertiary or some secondary alkyl halides, where the stability of the carbocation is a key factor in the reaction's feasibility.

Carbocation Stability

Carbocation stability is crucial in E1 reactions, as more stable carbocations are formed preferentially. Stability increases with the degree of substitution: tertiary carbocations are more stable than secondary, which are more stable than primary. This stability influences the rate of the reaction and the major product formed.

Regioselectivity in Elimination Reactions

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others. In E1 reactions, the formation of the double bond can lead to different alkene products, and the more substituted alkene (Zaitsev's rule) is typically favored due to greater stability. Understanding regioselectivity helps predict the major product in elimination reactions.

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