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

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)

Organic Chemistry

8. Elimination Reactions

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)

Previous problemNext problem

6:31 minutes

Problem 50f

Textbook Question

For which of the following reactions would you expect elimination to be more favored than substitution?
(f)

Verified step by step guidance

Step 1: Understand the key factors that influence whether elimination or substitution is favored. These include the nature of the substrate, the type of base/nucleophile, the solvent, and the reaction conditions (temperature). Elimination reactions are generally favored by strong bases, higher temperatures, and sterically hindered substrates.

Step 2: Analyze the substrate. If the substrate is tertiary (3°), elimination is often favored over substitution due to steric hindrance, which makes it difficult for the nucleophile to attack the carbon directly for substitution.

Step 3: Consider the base/nucleophile. Strong, bulky bases (e.g., tert-butoxide) tend to favor elimination because they are sterically hindered and less likely to act as nucleophiles for substitution.

Step 4: Evaluate the solvent. Polar protic solvents (e.g., water, alcohols) tend to favor elimination reactions, especially E1 mechanisms, because they stabilize the carbocation intermediate formed during elimination.

Step 5: Assess the reaction conditions. Higher temperatures generally favor elimination reactions over substitution because elimination has a higher activation energy, and increased thermal energy helps overcome this barrier.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Elimination vs. Substitution Reactions

Elimination reactions involve the removal of atoms or groups from a molecule, resulting in the formation of a double bond, while substitution reactions involve replacing one atom or group with another. The preference for one type over the other can depend on factors such as the structure of the substrate, the nature of the leaving group, and the reaction conditions.

Zaitsev's Rule

Zaitsev's Rule states that in elimination reactions, the more substituted alkene (the one with more alkyl groups attached to the double bond) is typically the major product. This principle helps predict the outcome of elimination reactions and is crucial for understanding when elimination is favored over substitution.

Reaction Conditions

The conditions under which a reaction occurs, such as temperature, solvent, and concentration, can significantly influence whether elimination or substitution is favored. For example, higher temperatures often favor elimination reactions, while lower temperatures may favor substitution, making it essential to consider these factors when analyzing reaction pathways.

Watch next

Master Overview of the flowchart. with a bite sized video explanation from Johnny

Start learning