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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8:38 minutes

Problem 41a

Textbook Question

Propose a mechanism for the following reaction:

Verified step by step guidance

Step 1: Analyze the reactants and products. The reactants are ethane (CH₃CH₃) and tert-butyl hypochlorite (CH₃C(OCl)(CH₃)₂). The products are ethyl chloride (CH₃CH₂Cl) and tert-butanol (CH₃C(OH)(CH₃)₂). This suggests a radical substitution mechanism.

Step 2: Initiation step. The reaction is initiated by heat (Δ), which causes the homolytic cleavage of the O-Cl bond in tert-butyl hypochlorite, generating a tert-butoxy radical (CH₃C(O•)(CH₃)₂) and a chlorine radical (Cl•).

Step 3: Propagation step 1. The chlorine radical (Cl•) abstracts a hydrogen atom from ethane (CH₃CH₃), forming ethyl radical (CH₃CH₂•) and HCl.

Step 4: Propagation step 2. The ethyl radical (CH₃CH₂•) reacts with another molecule of tert-butyl hypochlorite (CH₃C(OCl)(CH₃)₂), forming ethyl chloride (CH₃CH₂Cl) and regenerating the tert-butoxy radical (CH₃C(O•)(CH₃)₂).

Step 5: Termination step. Two tert-butoxy radicals (CH₃C(O•)(CH₃)₂) combine to form tert-butanol (CH₃C(OH)(CH₃)₂), completing the reaction.

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Key Concepts

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

Reaction Mechanism

A reaction mechanism is a step-by-step description of how a chemical reaction occurs at the molecular level. It outlines the sequence of elementary steps, including bond breaking and formation, and the intermediates formed during the reaction. Understanding the mechanism helps predict the products and the conditions under which the reaction occurs.

Nucleophiles and Electrophiles

Nucleophiles are species that donate an electron pair to form a chemical bond, while electrophiles are electron-deficient species that accept an electron pair. In organic reactions, identifying the nucleophile and electrophile is crucial for proposing a mechanism, as it determines the direction of electron flow and the formation of products.

Transition States and Intermediates

Transition states are high-energy states that occur during the transformation from reactants to products, representing the point of maximum energy along the reaction pathway. Intermediates are species that are formed and consumed during the reaction but are not present in the final products. Understanding these concepts is essential for accurately depicting the mechanism and energy changes throughout the reaction.

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Textbook Question

How many alkyl halides are obtained from monochlorination of the alkanes in Problem 4 if stereoisomers are included?

Textbook Question

How many monochlorination products would be obtained if all stereoisomers are included?

Textbook Question

What is the major product obtained from treating an excess of each of the following compounds with Cl₂ in the presence of ultraviolet light at room temperature? Disregard stereoisomers.

Textbook Question

In the presence of an acid catalyst, acetaldehyde forms a trimer known as paraldehyde. Because it induces sleep when it is administered to animals in large doses, paraldehyde is used as a sedative or hypnotic. Propose a mechanism for the formation of paraldehyde.

Textbook Question

How many alkyl halides are obtained from monochlorination of the alkanes in Problem 4 if stereoisomers are included?

Textbook Question

How many monochlorination products can be obtained from the radical chlorination of methylcyclohexane? Disregard stereoisomers.

Textbook Question

Write the steps for formation of tetrachloromethane (CCl₄) from the reaction of methane with Cl₂ + hv.

Textbook Question

A possible alternative mechanism to that shown in Problem 47 for the monochlorination of methane involves the following propagation steps:

How do you know that the reaction does not take place by this mechanism?

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