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

10. Addition Reactions

Halohydrin

Organic Chemistry

10. Addition Reactions

Halohydrin

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Problem 48c

Textbook Question

In light of your answer to Assessment 9.47, predict the product of the following reactions we have seen previously where an alcohol is substituted for water.
(c)

Verified step by step guidance

Step 1: Analyze the reactants. The first reactant is a bicyclohexane structure with two methyl groups attached. The second reactant is chlorine gas (Cl₂) in the presence of an alcohol solvent (2-methyl-2-butanol). This suggests a substitution or addition reaction involving chlorine.

Step 2: Consider the role of the alcohol solvent. Alcohols can act as nucleophiles or solvents that stabilize intermediates. In this case, the alcohol is likely to participate in the reaction as a solvent, influencing the reaction pathway.

Step 3: Predict the reaction mechanism. Chlorine gas (Cl₂) typically undergoes homolytic cleavage under light or heat to form chlorine radicals. These radicals can initiate a radical substitution reaction, especially at the most reactive hydrogen positions in the bicyclohexane structure.

Step 4: Identify the most reactive hydrogen positions. In the bicyclohexane structure, the hydrogens on the bridgehead carbons are less reactive due to steric hindrance. The hydrogens on the methyl groups are more accessible and likely to be substituted by chlorine radicals.

Step 5: Predict the product. The chlorine radical will replace one of the hydrogens on the methyl groups, forming a chlorinated bicyclohexane derivative. The alcohol solvent stabilizes the reaction intermediates but does not directly participate in the substitution.

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Key Concepts

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

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In this process, the aromatic system donates electrons to the electrophile, forming a sigma complex, which then loses a proton to restore aromaticity. Understanding EAS is crucial for predicting the products of reactions involving aromatic compounds, such as the one presented in the question.

Alcohol as a Nucleophile

In organic reactions, alcohols can act as nucleophiles due to the presence of a lone pair of electrons on the oxygen atom. This property allows alcohols to participate in substitution reactions, where they can replace leaving groups like water. Recognizing the role of alcohols in nucleophilic substitution is essential for predicting the outcome of the reaction shown in the question.

Halogenation of Aromatic Compounds

Halogenation involves the introduction of halogen atoms (like chlorine) into an organic molecule, often through EAS mechanisms. In the presence of a halogen and a catalyst, aromatic compounds can undergo substitution reactions where a hydrogen atom is replaced by a halogen. Understanding the conditions and mechanisms of halogenation is vital for predicting the products of the reaction depicted in the question.

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Related Practice

Textbook Question

Suggest an alkene that could be used to make each of the following halohydrins.

(c)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br₂, H₂O ; (iv) Cl₂, CH₃OH.

(e)

Textbook Question

Predict the product of the following haloalkane syntheses.

(e)

Textbook Question

Halohydrin formation is a stereospecific reaction. Identify the products of halohydrin formation of the following diastereomeric alkenes to demonstrate this stereospecificity.

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br₂, H₂O ; (iv) Cl₂, CH₃OH;

(l)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br₂, H₂O ; (iv) Cl₂, CH₃OH

(f)

Textbook Question

Retrosynthetic analysis is the process of working backward to develop the synthesis of a new compound. In Chapter 10, we begin developing multistep syntheses in this manner. For now, try to work backward a single step by suggesting an alkene and a reagent that would give products (a)–(i). [Your answers should not include alkenes that undergo rearrangement to give the desired products.]

(i)

Textbook Question

What will be the major product obtained from the reaction of Br₂ with 1-butene if the reaction is carried out in

c. ethyl alcohol?

d. methyl alcohol?

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