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

Previous problemNext problem

6:15 minutes

Problem 6g

Textbook Question

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

Verified step by step guidance

Identify the structure of the alkane provided in the image. The molecule is 2,3-dimethylpentane, which is a branched alkane.

Determine the unique types of hydrogen atoms in the molecule. These are hydrogens attached to different carbon environments, such as primary, secondary, and tertiary carbons.

Consider the monochlorination reaction, which replaces one hydrogen atom with a chlorine atom. Each unique hydrogen environment will lead to a different alkyl halide product.

Account for stereoisomers. If the chlorination occurs at a chiral center, multiple stereoisomers (R and S configurations) will be formed for that specific product.

Count all possible alkyl halides, including stereoisomers, by analyzing each unique hydrogen environment and determining if the resulting product has chiral centers.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Monochlorination

Monochlorination is a radical substitution reaction where one chlorine atom replaces a hydrogen atom in an alkane. This process typically involves the formation of chlorine radicals, which abstract hydrogen atoms from the alkane, leading to the formation of alkyl halides. The reaction can yield multiple products due to the presence of different hydrogen atoms in the alkane structure, resulting in various alkyl halides.

Stereoisomerism

Stereoisomerism refers to the phenomenon where compounds have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of their atoms. In the context of alkyl halides, monochlorination can produce stereoisomers if the chlorine atom is added to a carbon that is chiral or if the resulting alkyl halide can exist in different configurations, such as cis and trans forms. This is crucial for determining the total number of distinct products formed.

Radical Mechanism

The radical mechanism involves a series of steps including initiation, propagation, and termination, which are characteristic of radical reactions. In monochlorination, the initiation step generates chlorine radicals, which then propagate by reacting with alkanes to form alkyl radicals and further chlorine radicals. Understanding this mechanism is essential for predicting the products and their quantities, including the potential for stereoisomer formation.

Watch next

Master The one reaction that alkanes will actually undergo. with a bite sized video explanation from Johnny

Start learning