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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7:17 minutes

Problem 39a

Textbook Question

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

Verified step by step guidance

Analyze the reaction conditions provided in the problem (e.g., reagents, solvents, and temperature) to determine the type of reaction mechanism involved (e.g., SN1, SN2, E1, or E2). This will help predict the major product.

Identify the starting material and determine the site of substitution or elimination based on the structure of the molecule and the reaction mechanism.

Consider the stability of the carbocation intermediate if the reaction proceeds via an SN1 or E1 mechanism. More stable carbocations (e.g., tertiary > secondary > primary) will lead to the major product.

For SN2 reactions, consider steric hindrance at the electrophilic carbon. Less hindered primary or secondary carbons are more likely to undergo substitution in SN2 mechanisms.

Determine the structure of the alkyl halide product based on the reaction mechanism and the regioselectivity or stereoselectivity of the reaction. Ignore stereoisomers as instructed in the problem.

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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 by replacing one or more hydrogen atoms with halogen atoms (F, Cl, Br, I). 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 (like a halogen) by a nucleophile. The mechanism can be either SN1 or SN2, depending on the structure of the alkyl halide and the conditions of the reaction. SN2 reactions are favored by primary alkyl halides due to steric accessibility, while SN1 reactions are more common with tertiary alkyl halides due to stability of the carbocation intermediate.

Reaction Yield

Reaction yield refers to the amount of product obtained from a chemical reaction compared to the theoretical maximum amount possible. Factors influencing yield include the structure of the starting materials, reaction conditions, and the presence of competing reactions. In the context of alkyl halides, the stability of the resulting product and the efficiency of the substitution mechanism play crucial roles in determining which alkyl halide will be produced in the greatest yield.

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

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What hydrocarbon with the same molecular formula as in part a forms three monochlorinated products? One is achiral and two are chiral.

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Explain why iodine (I₂) does not react with ethane, even though I₂ is more easily cleaved homolytically than the other halogens.

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