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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4:05 minutes

Problem 4e

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the structure of the given alkane. The provided structure is methylcyclopentane, which consists of a cyclopentane ring with a single methyl group attached to one of the carbons.

Step 2: Identify the types of hydrogen atoms present in the molecule. In methylcyclopentane, there are two types of hydrogens: (1) hydrogens on the cyclopentane ring and (2) hydrogens on the methyl group.

Step 3: Determine the number of unique carbon environments. The cyclopentane ring has five carbons, but due to symmetry, only two distinct environments exist: (a) the carbon attached to the methyl group and (b) the other carbons in the ring. The methyl group contributes a third unique environment.

Step 4: Consider monochlorination at each unique carbon environment. Chlorination can replace a hydrogen atom on any of these environments, leading to different alkyl chlorides. Disregard stereoisomers as stated in the problem.

Step 5: Count the number of unique alkyl chlorides formed. Each unique carbon environment leads to a distinct alkyl chloride. Therefore, the total number of alkyl chlorides corresponds to the number of unique carbon environments identified in Step 3.

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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 chemical reaction where one chlorine atom is introduced into an organic molecule, typically an alkane, through a free radical mechanism. This process involves the generation of free radicals, which react with the alkane to form alkyl chlorides. Understanding the conditions and mechanisms of monochlorination is essential for predicting the products formed during the reaction.

Alkyl Chlorides

Alkyl chlorides, or haloalkanes, are organic compounds derived from alkanes by replacing one or more hydrogen atoms with chlorine atoms. The structure and branching of the alkane influence the number of distinct alkyl chlorides that can be formed. Recognizing the different positions where chlorination can occur is crucial for determining the total number of products.

Stereoisomers

Stereoisomers are compounds that have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of their atoms. In the context of monochlorination, disregarding stereoisomers means that only unique structural isomers are counted, simplifying the analysis of the products. This concept is important for accurately determining the number of distinct alkyl chlorides formed from the reaction.

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