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

Hydrohalogenation

Organic Chemistry

10. Addition Reactions

Hydrohalogenation

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1:10 minutes

Problem 59a

Textbook Question

At the beginning of Chapter 9, we stated that after finishing Chapters 8 and 9, we would have the ability to make a large variety of functional groups using related reactions. Show the reagent(s) necessary to convert 1-isobutylcyclohexene into the following molecules.
(a)

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Analyze the structure of 1-isobutylcyclohexene. It contains a cyclohexene ring with a double bond and an isobutyl group attached to the ring. Identify the functional group transformations required for the target molecule.

Determine the type of reaction needed to modify the double bond in the cyclohexene ring. For example, if the target molecule requires an alcohol, consider hydroboration-oxidation or oxymercuration-demercuration.

If the target molecule involves oxidation or reduction, select the appropriate reagents. For example, to oxidize the double bond to an epoxide, use a peracid like mCPBA. To reduce the double bond, use hydrogen gas (H₂) with a metal catalyst like Pd/C.

If the isobutyl group needs to be modified, identify the necessary reagents. For example, if the target molecule requires oxidation of the isobutyl group to a carboxylic acid, use a strong oxidizing agent like KMnO₄ or CrO₃ under acidic conditions.

Combine the steps logically, ensuring that the reagents and reaction conditions are compatible with the functional groups present in the molecule. Write out the sequence of reactions and reagents required to achieve the transformation.

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Key Concepts

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

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Understanding functional groups is essential in organic chemistry as they dictate the reactivity and properties of compounds. Examples include hydroxyl (-OH), carboxyl (-COOH), and amine (-NH2) groups, each influencing how a molecule interacts with others.

Reagents in Organic Reactions

Reagents are substances that are added to a system to cause a chemical reaction or to see if a reaction occurs. In organic chemistry, different reagents are used to facilitate transformations between functional groups. For instance, reagents like bromine (Br2) can be used for halogenation, while sulfuric acid (H2SO4) can promote dehydration reactions, making it crucial to select the appropriate reagent for the desired transformation.

Reaction Mechanisms

A reaction mechanism is a step-by-step description of the process by which reactants are converted into products. Understanding mechanisms helps predict the outcome of reactions and the conditions required for them. Key concepts include nucleophiles and electrophiles, transition states, and intermediates, which are vital for comprehending how and why specific reagents lead to particular functional group transformations.

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Related Practice

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions:(ii) HCl

(g)

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (i) HBr

(k)

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions:(ii) HCl

(k)

Textbook Question

Imagine an electrophilic addition where the first step is exothermic. Which carbocation—2°, 3°, or neither—would you expect to form preferentially? Explain.

Textbook Question

Specify the conditions that would allow the synthesis of the 1° and 3° bromoalkanes from the same starting alkene.

Textbook Question

The following haloalkanes can all be prepared starting from the same alkene. Give the alkene and the reagents needed for each.

Textbook Question

Predict the product and provide a mechanism for the reaction of 1-methylcyclohexene with HBr.

Textbook Question

Provide a mechanism for the following reactions occurring with rearrangement.

(b)

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At the beginning of Chapter 9, we stated that after finishing Chapters 8 and 9, we would have the ability to make a large variety of functional groups using related reactions. Show the reagent(s) necessary to convert 1-isobutylcyclohexene into the following molecules.(a)

Key Concepts

Functional Groups

Reagents in Organic Reactions

Reaction Mechanisms

Watch next

At the beginning of Chapter 9, we stated that after finishing Chapters 8 and 9, we would have the ability to make a large variety of functional groups using related reactions. Show the reagent(s) necessary to convert 1-isobutylcyclohexene into the following molecules.
(a)