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)

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Problem 56g

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the reactants and reaction conditions. The starting material is a tertiary alkyl chloride, and the reagent is a strong base (tert-butanol, which can act as a base due to its hydroxyl group). This suggests that the reaction could proceed via an elimination mechanism (E2 or E1) rather than substitution, as tertiary alkyl halides favor elimination due to steric hindrance.

Step 2: Determine the mechanism. Since tert-butanol is a bulky base, it will favor the E2 elimination mechanism. In E2 elimination, the base abstracts a proton from a β-carbon, and the leaving group (Cl) departs simultaneously, forming a double bond.

Step 3: Identify the β-hydrogens available for elimination. The β-carbons are the carbons adjacent to the carbon bonded to the chlorine atom. In this case, there are two β-carbons, each with hydrogens that can be abstracted.

Step 4: Predict the major product based on Zaitsev's rule. Zaitsev's rule states that the more substituted alkene will be the major product. Therefore, elimination will likely occur to form the more substituted double bond, resulting in the major product being the more stable alkene.

Step 5: Consider stereochemistry. In E2 elimination, the β-hydrogen and the leaving group must be anti-periplanar (opposite sides of the molecule in the same plane). Ensure that the stereochemical arrangement allows for this geometry during elimination.

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Key Concepts

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

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group in a molecule by a nucleophile. These reactions can occur via two main mechanisms: SN1, which is a two-step process involving carbocation formation, and SN2, which is a one-step process where the nucleophile attacks the substrate simultaneously as the leaving group departs. Understanding the mechanism is crucial for predicting the products and their stereochemistry.

Elimination Reactions

Elimination reactions involve the removal of a leaving group and a hydrogen atom from adjacent carbon atoms, resulting in the formation of a double bond. The two primary types are E1, which proceeds through a carbocation intermediate, and E2, which is a concerted process. The choice between substitution and elimination often depends on the structure of the substrate and the reaction conditions, influencing the final product.

Stereochemistry

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In substitution and elimination reactions, the stereochemical outcome can be significant, especially in SN2 reactions, which result in inversion of configuration, and in E2 reactions, where the stereochemistry of the starting material can dictate the geometry of the double bond formed. Understanding stereochemistry is essential for predicting the correct products.

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