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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Problem 55e

Textbook Question

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

Verified step by step guidance

Step 1: Identify the type of elimination reaction. The presence of a strong base, such as tert-butanol (t-BuOH), suggests that this reaction will likely proceed via an E2 mechanism. In an E2 reaction, the base abstracts a proton from a β-carbon, and the leaving group (Cl) departs simultaneously, forming a double bond.

Step 2: Analyze the stereochemistry of the substrate. The molecule contains a cyclohexane ring with a chlorine atom as the leaving group. For an E2 reaction, the β-hydrogen and the leaving group must be anti-periplanar (i.e., opposite sides of the plane). Check the stereochemistry of the β-hydrogens relative to the chlorine atom.

Step 3: Determine the β-hydrogens available for elimination. In this case, the β-hydrogens are located on the carbons adjacent to the carbon bearing the chlorine atom. Evaluate which β-hydrogen is anti-periplanar to the chlorine atom and can be abstracted by the base.

Step 4: Predict the major product based on Zaitsev's rule. Zaitsev's rule states that the most substituted alkene is generally the major product in elimination reactions. Consider the possible double bonds that can form and identify the most stable (most substituted) alkene.

Step 5: Consider stereochemical outcomes. Since the reaction proceeds via an E2 mechanism, the stereochemistry of the product will depend on the anti-periplanar geometry of the β-hydrogen and the leaving group. Draw the major product with the correct stereochemistry and confirm that it follows the rules of elimination.

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Key Concepts

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

Elimination Reactions

Elimination reactions involve the removal of atoms or groups from a molecule, resulting in the formation of a double bond. Common types include E1 and E2 mechanisms, which differ in their reaction pathways and conditions. Understanding the mechanism is crucial for predicting the products, as it influences the stereochemistry and regioselectivity of the reaction.

Stereochemistry

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In elimination reactions, the stereochemical outcome can lead to different products, such as cis or trans isomers. Recognizing the stereochemical implications is essential for accurately predicting the major product of the reaction.

Regioselectivity

Regioselectivity is the preference of a chemical reaction to yield one structural isomer over others when multiple products are possible. In elimination reactions, this concept helps determine which alkene product is favored based on factors like stability and sterics. Understanding regioselectivity is key to predicting the major product in elimination reactions.

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Related Practice

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?

Textbook Question

For each of the following compounds, draw the product that forms in an E2 reaction and indicate its configuration:

a. (1S,2S)-1-bromo-1,2-diphenylpropane

Textbook Question

When (1-bromoethyl)cyclohexane is heated in methanol for an extended period of time, five products result: two ethers and three alkenes. Predict which of the three alkenes is the major elimination product.

Textbook Question

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

(a)

Textbook Question

When using sulfuric acid, but in the absence of other nucleophiles like water or bromide ion, less stable alkenes can be isomerized to their more stable isomer. Provide a mechanism for these acid-catalyzed isomerization reactions. [This is one illustration of the principle of microscopic reversibility.]

(b)

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

Key Concepts

Elimination Reactions

Stereochemistry

Regioselectivity

Watch next

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