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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3:55 minutes

Problem 4b

Textbook Question

How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
b.

Verified step by step guidance

Step 1: Identify the structure of the given alkane. The provided structure is 2,3-dimethylpentane, which is a branched alkane.

Step 2: Determine all unique types of hydrogen atoms in the molecule. Hydrogens attached to different carbon environments will lead to different alkyl chlorides upon monochlorination. In this molecule, there are primary, secondary, and tertiary hydrogens.

Step 3: Count the number of unique carbon environments. The molecule has primary carbons (at the ends of the chain), secondary carbons (connected to two other carbons), and tertiary carbons (connected to three other carbons). Each unique carbon environment corresponds to a unique alkyl chloride upon monochlorination.

Step 4: Disregard stereoisomers as instructed. Focus only on the unique carbon environments, not the spatial arrangement of substituents.

Step 5: Sum up the number of unique alkyl chlorides formed. Each unique carbon environment will produce one type of alkyl chloride upon monochlorination.

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Key Concepts

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

Monochlorination

Monochlorination is a specific type of halogenation where one chlorine atom replaces a hydrogen atom in an alkane. This process typically occurs through a free radical mechanism, which involves the generation of chlorine radicals that abstract hydrogen atoms from the alkane, leading to the formation of alkyl chlorides. Understanding this process is crucial for predicting the products formed during the reaction.

Free Radical Mechanism

The free radical mechanism is a reaction pathway that involves the formation and reaction of free radicals, which are highly reactive species with unpaired electrons. In the context of monochlorination, the mechanism consists of three main steps: initiation, propagation, and termination. Each step plays a vital role in determining the number and types of alkyl chlorides produced from the starting alkane.

Alkyl Chlorides

Alkyl chlorides are organic compounds derived from alkanes by substituting one or more hydrogen atoms with chlorine atoms. The structure and branching of the original alkane influence the variety of alkyl chlorides formed during monochlorination. Identifying the different alkyl chlorides is essential for understanding the outcomes of the chlorination reaction and for predicting their chemical behavior.

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