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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5:20 minutes

Problem 35a

Textbook Question

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

Verified step by step guidance

Step 1: Identify the reaction type. The problem specifies an E1 reaction, which is a unimolecular elimination reaction. In an E1 reaction, the rate-determining step involves the formation of a carbocation intermediate after the leaving group departs.

Step 2: Analyze the structure of the compound. The given compound is a tertiary alkyl bromide, which is ideal for an E1 reaction because tertiary carbocations are more stable due to hyperconjugation and inductive effects.

Step 3: Determine the leaving group. Bromine (Br) is the leaving group in this molecule. It will depart, forming a carbocation at the tertiary carbon.

Step 4: Consider the possible rearrangements and stability of the carbocation. Since the carbocation is already tertiary, no rearrangement is necessary. The tertiary carbocation is stable and will proceed to the next step.

Step 5: Identify the major product. In an E1 reaction, the elimination of a proton from a β-carbon occurs, forming a double bond. The major product will be the most substituted alkene (Zaitsev's rule), which is formed by removing a proton from the β-carbon that leads to the most stable 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 is a type of elimination reaction that occurs in two steps. The first step involves the formation of a carbocation intermediate after the leaving group departs, while the second step involves the removal of a proton to form a double bond. This mechanism is favored in tertiary and some secondary substrates due to the stability of the carbocation formed.

Carbocation Stability

Carbocation stability is a crucial factor in determining the outcome of E1 reactions. Tertiary carbocations are more stable than secondary or primary ones due to hyperconjugation and inductive effects from surrounding alkyl groups. The more stable the carbocation, the more likely it is to form, influencing the major product of the reaction.

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 depending on the stability of the resulting alkenes. The more substituted alkene is typically favored due to greater stability, following Zaitsev's rule.

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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

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

Draw the major product obtained when an alkyl halide in [PROBLEM 9-83] undergoes 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)

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

Key Concepts

E1 Reaction Mechanism

Carbocation Stability

Regioselectivity in Elimination Reactions

Watch next

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