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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4:40 minutes

Problem 38b

Textbook Question

Draw the substitution and elimination products for the following reactions, showing the configuration of each product:
b. cis-1-chloro-2-methylcyclohexane + CH₃O⁻

Verified step by step guidance

Analyze the structure of the starting material, cis-1-chloro-2-methylcyclohexane. The chlorine atom is on one carbon of the cyclohexane ring, and the methyl group is on the adjacent carbon. Both substituents are on the same side of the ring (cis configuration).

Identify the reagent, CH3O− (methoxide ion), which is a strong base and a good nucleophile. This means that both substitution (SN2 or SN1) and elimination (E2 or E1) reactions are possible, depending on the reaction conditions.

For the substitution product: In an SN2 reaction, the methoxide ion will attack the carbon bonded to the chlorine atom (the leaving group) from the opposite side, leading to an inversion of configuration at that carbon. Draw the product with the methoxy group replacing the chlorine, ensuring the stereochemistry reflects the inversion.

For the elimination product: In an E2 reaction, the methoxide ion will abstract a β-hydrogen (a hydrogen on a carbon adjacent to the carbon bearing the chlorine). Since the starting material is in the cis configuration, consider the anti-periplanar geometry required for E2 elimination. Draw the resulting alkene, ensuring the correct stereochemistry of the double bond.

Verify the stereochemistry of all products. For the substitution product, confirm the inversion of configuration. For the elimination product, ensure the double bond is correctly placed and the stereochemistry of the alkene (E or Z) is consistent with the starting material's geometry.

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Key Concepts

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

Substitution Reactions

Substitution reactions involve the replacement of one functional group in a molecule with another. In organic chemistry, this often occurs with alkyl halides, where a nucleophile attacks the carbon atom bonded to the leaving group (e.g., Cl) and replaces it. Understanding the mechanism (SN1 or SN2) is crucial, as it influences the stereochemistry and the nature of the products formed.

Elimination Reactions

Elimination reactions involve the removal of a small molecule (like HCl or H2O) from a larger molecule, resulting in the formation of a double bond. In the context of the given reaction, the base (CH3O−) abstracts a proton, leading to the formation of an alkene. The regioselectivity and stereochemistry of the elimination products depend on the structure of the starting material and the reaction conditions.

Stereochemistry

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the context of the given reaction, the configuration of the products (cis or trans) is important, especially when dealing with cyclic compounds like cyclohexane. Understanding how stereochemistry influences reactivity and product formation is essential for predicting the outcomes of substitution and elimination reactions.

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