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

9. Alkenes and Alkynes

Zaitsev Rule

Organic Chemistry

9. Alkenes and Alkynes

Zaitsev Rule

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5:22 minutes

Problem 84d

Textbook Question

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

Verified step by step guidance

Step 1: Identify the alkyl halide structure provided in the image. The molecule consists of a cyclopentane ring with a tertiary carbon attached to a chlorine atom and an ethyl group (CH2CH3). This is a tertiary alkyl halide, which is prone to undergoing an E1 elimination reaction.

Step 2: Understand the mechanism of an E1 reaction. E1 elimination involves two steps: (1) the formation of a carbocation intermediate after the leaving group (Cl) departs, and (2) the elimination of a proton from a β-carbon to form a double bond.

Step 3: Predict the carbocation intermediate. When the chlorine atom leaves, a tertiary carbocation forms at the carbon attached to the cyclopentane ring and the ethyl group. Tertiary carbocations are highly stable due to hyperconjugation and inductive effects.

Step 4: Determine the β-hydrogens available for elimination. The β-carbons are the carbons adjacent to the carbocation. In this case, there are β-hydrogens on the cyclopentane ring and the ethyl group. The elimination of a β-hydrogen leads to the formation of a double bond.

Step 5: Draw the major product. The major product is determined by Zaitsev's rule, which states that the more substituted alkene is favored. Elimination of a β-hydrogen from the cyclopentane ring will result in a double bond between the cyclopentane ring and the tertiary carbon, forming the more substituted alkene.

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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 involves two main steps: the formation of a carbocation intermediate after the departure of a leaving group, followed by the elimination of a proton to form a double bond. This mechanism is favored in tertiary and some secondary alkyl halides due to the stability of the carbocation formed. The rate of the reaction depends only on the concentration of the alkyl halide.

Carbocation Stability

Carbocation stability is crucial in E1 reactions, as more stable carbocations lead to faster reactions. Stability increases with the degree of substitution: tertiary carbocations are more stable than secondary, which are more stable than primary. Factors such as hyperconjugation and inductive effects from adjacent alkyl groups contribute to this stability, influencing the product distribution in elimination reactions.

Zaitsev's Rule

Zaitsev's Rule states that in elimination reactions, the more substituted alkene is typically the major product. This occurs because the formation of more stable alkenes is favored, as they have lower energy due to greater hyperconjugation and alkyl substitution. Understanding this rule helps predict the outcome of E1 reactions, particularly when multiple elimination products are possible.

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Related Practice

Textbook Question

Which alkyl halide in each pair is more reactive in an E2 reaction with hydroxide ion?

Textbook Question

For each of the following alkyl halides, indicate the stereoisomer that would be obtained in greatest yield in an E2 reaction.

c. 3-bromo-2,3-dimethylpentane

d. 3-bromo-3,4-dimethylhexane

Textbook Question

For each of the following alkyl halides, indicate the stereoisomer that would be obtained in greatest yield in an E2 reaction.

d. 3-bromo-3,4-dimethylhexane

Textbook Question

What is the major product formed when the following compounds undergo an E1 reaction?

Textbook Question

Predict the products of E1 elimination of the following compounds. Label the major products.

(c)

Textbook Question

What is the major product formed when the following compounds undergo an E1 reaction?

Textbook Question

Predict the major product(s) of the following elimination reactions, paying close attention to the stereochemical outcome of the reactions.

(c)

Textbook Question

What is the major product formed when the following compounds undergo an E1 reaction?

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

Key Concepts

E1 Reaction Mechanism

Carbocation Stability

Zaitsev's Rule

Watch next

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