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

Cumulative Substitution/Elimination

Organic Chemistry

8. Elimination Reactions

Cumulative Substitution/Elimination

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5:44 minutes

Problem 44c

Textbook Question

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

Verified step by step guidance

Step 1: Identify the type of elimination reaction. The presence of NaOH and H2O suggests that this is likely an E2 elimination reaction, as NaOH is a strong base.

Step 2: Analyze the stereochemistry of the molecule. The bromine atom is attached to a carbon that is adjacent to a β-hydrogen. Note that the β-hydrogen must be anti-periplanar to the leaving group (Br) for the E2 mechanism to proceed.

Step 3: Determine the possible β-hydrogens. In this case, there are two β-hydrogens available on the adjacent carbons. Evaluate which β-hydrogen is anti-periplanar to the bromine atom.

Step 4: Predict the double bond formation. The elimination of HBr will result in the formation of a double bond between the α-carbon (where Br is attached) and the β-carbon (where the β-hydrogen is removed). Consider the Zaitsev rule, which states that the more substituted alkene is generally favored.

Step 5: Draw the product with the correct stereochemistry. Ensure that the stereochemical outcome reflects the anti-periplanar geometry required for the E2 mechanism. The final product will be an alkene with the appropriate stereochemistry based on the starting material.

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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 a small molecule from a larger one, typically resulting in the formation of a double bond. In organic chemistry, common elimination reactions include E1 and E2 mechanisms, which differ in their steps and conditions. Understanding the mechanism is crucial for predicting the stereochemical outcome of the reaction.

Stereochemistry

Stereochemistry refers to the study of 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, depending on the orientation of the leaving groups and the formation of the double bond. Recognizing stereochemical configurations is essential for accurate product prediction.

Base Strength and Nucleophilicity

The strength of the base used in elimination reactions significantly influences the reaction pathway and product formation. Strong bases, like NaOH, favor E2 mechanisms, leading to the formation of alkenes. Understanding the role of the base helps in predicting whether the reaction will proceed via a concerted mechanism or through carbocation intermediates, impacting the stereochemical outcome.

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