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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1:29 minutes

Problem 67d

Textbook Question

Using any alkene and any other reagents, how would you prepare the following compounds?
d.

Verified step by step guidance

Step 1: Identify the target molecule's functional groups. The compound contains a bromine (Br) and a hydroxyl group (OH) attached to adjacent carbons, indicating a vicinal halohydrin structure.

Step 2: Choose an appropriate alkene precursor. The target molecule can be synthesized from 2-hexene (CH3CH=CHCH2CH2CH3), as the double bond provides the reactive site for addition reactions.

Step 3: Select reagents for halohydrin formation. Use bromine (Br2) in the presence of water (H2O). This reaction involves electrophilic addition of Br2 to the alkene, followed by nucleophilic attack by water to form the halohydrin.

Step 4: Predict the regioselectivity and stereochemistry. The bromine adds to one carbon of the double bond, and the hydroxyl group adds to the adjacent carbon. The reaction proceeds via anti-addition, resulting in the bromine and hydroxyl group being on opposite sides of the molecule.

Step 5: Verify the product structure. Ensure that the bromine and hydroxyl group are attached to the correct carbons (C3 and C4 in the hexane chain) and that the stereochemistry matches the target molecule.

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Key Concepts

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

Alkene Reactivity

Alkenes are unsaturated hydrocarbons characterized by at least one carbon-carbon double bond. Their reactivity is primarily due to this double bond, which can undergo various reactions such as addition, oxidation, and polymerization. Understanding the types of reactions that alkenes can participate in is crucial for synthesizing target compounds.

Addition Reactions

Addition reactions involve the addition of atoms or groups to the carbon atoms of the double bond in alkenes, resulting in the formation of saturated compounds. Common addition reactions include hydrogenation, halogenation, and hydrohalogenation. Recognizing the specific reagents and conditions required for these reactions is essential for preparing desired products from alkenes.

Functional Group Transformation

Functional group transformation refers to the process of converting one functional group into another through chemical reactions. This concept is vital in organic synthesis, as it allows chemists to modify the structure and reactivity of molecules. Identifying the appropriate reagents and reaction conditions for transforming functional groups is key to achieving the desired compound from an alkene.

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Related Practice

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?

Textbook Question

1-Methylcyclohexene forms two products when it reacts with bromine in methanol.

a. Draw the mechanism for the formation of the products.

b. Describe their stereochemical relationship—that is, are they enantiomers or diastereomers?

Textbook Question

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

a. dichloromethane?

b. water?

Textbook Question

Each of the following reactions has two nucleophiles that could add to the intermediate formed by the reaction of the alkene with an electrophile. What is the major product of each reaction?

Textbook Question

What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?

j. Br₂/CH₃OH

Textbook Question

A graduate student attempted to form the iodohydrin of the alkene shown below. Her analysis of the products showed a good yield of an unexpected product. Propose a mechanism to explain the formation of this product.

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Using any alkene and any other reagents, how would you prepare the following compounds?d.

Key Concepts

Alkene Reactivity

Addition Reactions

Functional Group Transformation

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Using any alkene and any other reagents, how would you prepare the following compounds?
d.