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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2:02 minutes

Problem 6b

Textbook Question

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

Verified step by step guidance

Step 1: Identify the structure of the alkane provided in the image. The structure is 2,3-dimethylbutane, which is a branched alkane.

Step 2: Determine the possible sites for monochlorination. Monochlorination involves replacing one hydrogen atom with a chlorine atom. Analyze the molecule to find all unique hydrogen environments (primary, secondary, tertiary hydrogens).

Step 3: Consider the symmetry of the molecule. Due to the symmetry in 2,3-dimethylbutane, some hydrogen environments will be equivalent, reducing the number of unique products.

Step 4: Account for stereoisomers. If monochlorination occurs at a chiral center, stereoisomers (R and S configurations) must be considered as separate products.

Step 5: Count all unique alkyl halides, including stereoisomers, formed from monochlorination at each unique hydrogen environment. This will give the total number of alkyl halides obtained.

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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 (such as chlorine, bromine, or iodine). 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 their reactivity and the products formed during reactions like halogenation.

Free Radical Halogenation

Free radical halogenation is a reaction mechanism where alkanes react with halogens (like Cl2 or Br2) in the presence of heat or light to form alkyl halides. This process involves the formation of free radicals, which are highly reactive species with unpaired electrons. The reaction proceeds through initiation, propagation, and termination steps, and understanding this mechanism is essential for predicting the products and their stereochemistry.

Stereoisomerism

Stereoisomerism occurs when compounds have the same molecular formula and connectivity but differ in the spatial arrangement of their atoms. In the context of alkyl halides, the presence of chiral centers can lead to the formation of enantiomers or diastereomers. Recognizing the potential for stereoisomers is important when determining the total number of distinct products formed from reactions like monochlorination, as each stereoisomer represents a unique compound.

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