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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5:03 minutes

Problem 20b

Textbook Question

When (1R,3S)-1-tert-butyl-1,3-dimethylcyclopentane is halogenated, one stereoisomer is produced in excess.
(b) explain why this reaction did not produce an equal mixture of stereoisomers.

Verified step by step guidance

Identify the type of reaction: Halogenation of alkanes typically proceeds via a radical mechanism, which involves the formation of a radical intermediate.

Consider the stereochemistry: The starting material, (1R,3S)-1-tert-butyl-1,3-dimethylcyclopentane, has chiral centers. The reaction can lead to the formation of different stereoisomers depending on the radical intermediate's stability and the approach of the halogen.

Analyze the radical stability: In radical halogenation, the most stable radical intermediate is favored. The tertiary radical at the 1-position (where the tert-butyl group is attached) is more stable than a secondary or primary radical due to hyperconjugation and inductive effects.

Predict the major product: The formation of the more stable radical intermediate leads to a preference for one stereoisomer over others. The major product will be the one where the halogen adds to the most stable radical, maintaining the configuration at the other chiral center.

Explain the excess of one stereoisomer: The reaction does not produce an equal mixture of stereoisomers because the formation of the more stable radical intermediate is favored, leading to a predominant formation of one stereoisomer over the others.

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Key Concepts

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

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and its impact on chemical reactions. In this context, understanding the stereochemistry of (1R,3S)-1-tert-butyl-1,3-dimethylcyclopentane is crucial, as the configuration of its chiral centers influences the formation of specific stereoisomers during halogenation.

Chiral Centers

Chiral centers are atoms in a molecule that have four different substituents, leading to non-superimposable mirror images called enantiomers. The presence of chiral centers in (1R,3S)-1-tert-butyl-1,3-dimethylcyclopentane results in stereoisomers, and the reaction conditions can favor the formation of one stereoisomer over another due to steric and electronic effects.

Reaction Mechanism

The reaction mechanism describes the step-by-step process by which reactants are transformed into products. In halogenation, factors such as steric hindrance and electronic effects can influence the pathway, leading to the preferential formation of one stereoisomer. Understanding the mechanism helps explain why an unequal mixture of stereoisomers is produced.

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Related Practice

Textbook Question

Show how free-radical halogenation might be used to synthesize the following compounds. In each case, explain why we expect to get a single major product.

(a) 1-chloro-2,2-dimethylpropane (neopentyl chloride)

(b) 2-bromo-2-methylbutane

Textbook Question

Rationalize the fact that reaction A results in an unequal mixture of products, but reaction B yields an equal mixture of two products.

Textbook Question

Because of the angle strain present in cyclopropanes, they tend to open up in the presence of nearby radicals. Show a mechanism for the following reaction that demonstrates this principle.

Textbook Question

When (1R,3S)-1-tert-butyl-1,3-dimethylcyclopentane is halogenated, one stereoisomer is produced in excess.

(a) Predict the identity of the major stereoisomer

Textbook Question

Predict the major products of the following alkane halogenation reactions. [The number of products shown ignores the formation of racemic mixtures.]

(b)

Textbook Question

Predict the major products of the following alkane halogenation reactions. [The number of products shown ignores the formation of racemic mixtures.]

(d)

Textbook Question

Can you make a 1° bromoalkane like (3-bromopropyl)cyclopentane using alkane halogenation? Why or why not?

Textbook Question

Predict the major product of the following bromination reactions.

(b)

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When (1R,3S)-1-tert-butyl-1,3-dimethylcyclopentane is halogenated, one stereoisomer is produced in excess.(b) explain why this reaction did not produce an equal mixture of stereoisomers.

Key Concepts

Stereochemistry

Chiral Centers

Reaction Mechanism

Watch next

When (1R,3S)-1-tert-butyl-1,3-dimethylcyclopentane is halogenated, one stereoisomer is produced in excess.
(b) explain why this reaction did not produce an equal mixture of stereoisomers.