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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3:59 minutes

Problem 6f

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the structure of the given alkane. The molecule is a cyclopentane ring with a single ethyl group attached to one of the carbons in the ring. This is a substituted cycloalkane.

Step 2: Identify all unique types of hydrogen atoms in the molecule. Hydrogens attached to different types of carbons (primary, secondary, tertiary) will lead to different alkyl halides upon monochlorination.

Step 3: Consider the symmetry of the molecule. The cyclopentane ring is symmetric, and the ethyl group introduces asymmetry. This affects the number of unique positions for chlorination.

Step 4: Account for stereoisomers. If chlorination occurs at a chiral center, stereoisomers (R and S configurations) must be included in the count of alkyl halides.

Step 5: Determine the total number of alkyl halides by considering all unique positions for chlorination and including stereoisomers where applicable. Each unique position corresponds to a distinct alkyl halide.

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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 can be classified as primary, secondary, or tertiary based on the carbon atom to which the halogen is attached. Understanding the structure and classification of alkyl halides is crucial for predicting the products of reactions such as halogenation.

Monochlorination

Monochlorination refers to the substitution reaction where one hydrogen atom in an alkane is replaced by a chlorine atom. This process typically involves free radical mechanisms, where chlorine radicals abstract hydrogen atoms, leading to the formation of various alkyl chlorides. The reaction can yield multiple products, including stereoisomers, depending on the structure of the starting alkane.

Stereoisomerism

Stereoisomerism occurs when compounds have the same molecular formula and connectivity but differ in the spatial arrangement of atoms. In the context of alkyl halides, the presence of chiral centers can lead to different stereoisomers, such as enantiomers and diastereomers. Recognizing and counting these stereoisomers is essential when determining the total number of products from reactions like monochlorination.

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Related Practice

Textbook Question

What are the product(s) of each of the following reactions? Disregard stereoisomers.