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

4:28 minutes

Problem 44a

Textbook Question

Paying close attention to the stereochemical outcome, predict the product of these elimination reactions.
(a)

Verified step by step guidance

Identify the type of elimination reaction (E1 or E2) based on the reaction conditions. For example, strong bases and high temperatures typically favor E2, while weak bases and polar protic solvents favor E1.

Determine the structure of the starting material, including the location of the leaving group and any β-hydrogens (hydrogens on the carbon adjacent to the carbon bearing the leaving group).

For E2 reactions, consider the anti-periplanar geometry requirement. The β-hydrogen and the leaving group must be in opposite planes (180° apart) for the elimination to occur. Rotate the molecule, if necessary, to visualize this geometry.

For E1 reactions, the first step is the formation of a carbocation intermediate after the leaving group departs. Assess the stability of the carbocation and consider any possible rearrangements (e.g., hydride or alkyl shifts) that could lead to a more stable carbocation.

Once the elimination occurs, predict the major product by applying Zaitsev's rule (the more substituted alkene is generally favored) while also considering stereochemical outcomes, such as the formation of E (trans) or Z (cis) isomers, depending on the steric and electronic factors.

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 Reactions

Elimination reactions involve the removal of atoms or groups from a molecule, resulting in the formation of a double bond or a ring structure. Common types include E1 and E2 mechanisms, which differ in their reaction pathways and stereochemical outcomes. Understanding the conditions and mechanisms of these reactions is crucial for predicting the products formed.

Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In elimination reactions, the stereochemical configuration of the starting material can influence the orientation of the double bond formed, leading to different stereoisomers. Recognizing the importance of stereochemistry is essential for predicting the correct product.

Zaitsev's Rule

Zaitsev's Rule states that in elimination reactions, the more substituted alkene is typically the major product. This principle helps predict the outcome of reactions by favoring the formation of more stable alkenes, which are generally more substituted. Understanding this rule aids in anticipating the products based on the structure of the reactants.

Watch next

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

Start learning