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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6:32 minutes

Problem 49c

Textbook Question

Predict the products of E1 elimination of the following compounds. Label the major products.
(c)

Verified step by step guidance

Step 1: Understand the E1 elimination mechanism. E1 elimination involves two steps: (1) the leaving group departs, forming a carbocation intermediate, and (2) a proton is removed from a β-carbon by a base, resulting in the formation of a double bond. The reaction typically favors the formation of the most stable alkene (Zaitsev's rule).

Step 2: Identify the structure of the given compound, (CH3)3C-CH(CH3)Br. The molecule consists of a tertiary carbon bonded to a bromine atom (the leaving group) and a secondary carbon with a methyl group attached.

Step 3: Determine the carbocation intermediate. When the bromine leaves, a tertiary carbocation forms at the central carbon atom (C1), as tertiary carbocations are more stable due to hyperconjugation and inductive effects.

Step 4: Analyze the β-hydrogens available for elimination. The β-carbons are adjacent to the carbocation (C2 and C3). C2 has one hydrogen atom, and C3 has three hydrogen atoms. Removing a β-hydrogen from either carbon will result in the formation of a double bond.

Step 5: Apply Zaitsev's rule to predict the major product. Zaitsev's rule states that the most substituted alkene is the major product. Removing a β-hydrogen from C2 will form a double bond between C1 and C2, resulting in a more substituted alkene compared to removing a β-hydrogen from C3. Label the alkene formed by elimination at C2 as 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 Elimination Mechanism

The E1 elimination mechanism involves two main steps: the formation of a carbocation intermediate after the leaving group departs, followed by the removal of a proton to form a double bond. This mechanism is favored in tertiary substrates due to their ability to stabilize the carbocation, leading to the formation of alkenes as products.

Carbocation Stability

Carbocation stability is crucial in determining the pathway of elimination reactions. Tertiary carbocations are more stable than secondary or primary ones due to hyperconjugation and inductive effects from surrounding alkyl groups. In the given compound, the formation of a tertiary carbocation will significantly influence the major product of the E1 reaction.

Zaitsev's Rule

Zaitsev's Rule states that in elimination reactions, the more substituted alkene is typically the major product. This is because more substituted alkenes are generally more stable due to hyperconjugation and steric factors. When predicting the products of the E1 elimination for the given compound, identifying the more substituted alkene will help in labeling the major product.

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Related Practice

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

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

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

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

(e)

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Predict the products of E1 elimination of the following compounds. Label the major products.(c)

Key Concepts

E1 Elimination Mechanism

Carbocation Stability

Zaitsev's Rule

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Predict the products of E1 elimination of the following compounds. Label the major products.
(c)