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

11. Radical Reactions

Free Radical Halogenation

Organic Chemistry

11. Radical Reactions

Free Radical Halogenation

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5:48 minutes

Problem 39b

Textbook Question

What alkyl halide will be obtained in greatest yield? Ignore stereoisomers.
b.

Verified step by step guidance

Identify the starting material and the reaction conditions provided in the problem. This will help determine the mechanism (SN1, SN2, E1, or E2) and the type of alkyl halide that will form.

Analyze the structure of the starting material to determine the most likely site for substitution or elimination. Consider factors such as the stability of the carbocation (if SN1 or E1) or the steric hindrance around the electrophilic carbon (if SN2 or E2).

If the reaction proceeds via an SN1 mechanism, predict the major product by identifying the most stable carbocation intermediate. Stability is influenced by factors such as resonance, hyperconjugation, and inductive effects.

If the reaction proceeds via an SN2 mechanism, predict the major product by considering the nucleophile's attack on the least sterically hindered carbon. The product will result from a backside attack, leading to inversion of configuration at the electrophilic carbon.

Once the mechanism is determined and the major product is identified, confirm that the product is an alkyl halide. The alkyl halide with the greatest yield will typically correspond to the most stable intermediate or the least sterically hindered pathway, depending on the mechanism.

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Key Concepts

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

Alkyl Halides

Alkyl halides are organic compounds derived from alkanes that contain one or more halogen atoms (F, Cl, Br, I) replacing hydrogen atoms. They are classified based on the number of carbon atoms attached to the carbon bearing the halogen: primary, secondary, or tertiary. The structure of the alkyl halide significantly influences its reactivity and the types of reactions it can undergo.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group (such as a halogen) by a nucleophile. The mechanism can follow either an SN1 or SN2 pathway, depending on the structure of the alkyl halide and the conditions of the reaction. Understanding these mechanisms is crucial for predicting which alkyl halide will yield the most product in a given reaction.

Steric Hindrance

Steric hindrance refers to the prevention of chemical reactions due to the spatial arrangement of atoms within a molecule. In the context of alkyl halides, tertiary alkyl halides are generally more reactive in SN1 reactions due to less steric hindrance, while primary alkyl halides are more reactive in SN2 reactions. Recognizing the impact of steric hindrance helps in determining which alkyl halide will be produced in the greatest yield.

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