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

Dihydroxylation

Organic Chemistry

10. Addition Reactions

Dihydroxylation

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1:42 minutes

Problem 59d

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.
(d)

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Analyze the structure of 1-isobutylcyclohexene. It contains a cyclohexene ring with an isobutyl group attached to one of the carbons in the double bond. Identify the functional group in the target molecule to determine the transformation required.

Determine the type of reaction needed to achieve the transformation. For example, if the target molecule involves the addition of a functional group to the double bond, consider reactions such as hydroboration-oxidation, halogenation, or epoxidation.

Select the appropriate reagent(s) for the reaction. For instance, if the target molecule is an alcohol, hydroboration-oxidation using BH₃·THF followed by H₂O₂/NaOH would be suitable. If the target is a halohydrin, use Br₂ in the presence of water.

Consider the regioselectivity and stereoselectivity of the reaction. For example, hydroboration-oxidation proceeds with anti-Markovnikov regioselectivity and syn addition, while halogenation with water forms a halohydrin with anti addition.

Write the reaction mechanism to confirm the transformation. Show how the reagent interacts with 1-isobutylcyclohexene to form the desired product, ensuring all intermediates and stereochemical outcomes are accounted for.

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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 bring about a chemical reaction or to see if a reaction occurs. In organic chemistry, different reagents are used to facilitate the transformation of one functional group into another. For instance, reagents like bromine (Br2) can be used for halogenation, while sulfuric acid (H2SO4) can promote dehydration reactions.

Reaction Mechanisms

A reaction mechanism is a step-by-step description of how a chemical reaction occurs at the molecular level. It outlines the sequence of events, including bond breaking and forming, that lead to the final products. Understanding mechanisms is crucial for predicting the outcomes of reactions and for designing synthetic pathways to create desired compounds from starting materials.

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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: (vi) 1. OsO₄ 2. NaHSO₃

(d)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vi) 1. OsO₄ 2. NaHSO₃

(h)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vi) 1. OsO₄ 2. NaHSO₃

(k)

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.

(b)

Textbook Question

The concertedness of the OsO₄ reaction results in both oxygens being added to the same face of the molecule (i.e., syn addition). How might these conditions be modified in order to prepare a trans-diol?

Textbook Question

Predict the product(s) of each of the following reactions, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers.

(b)

Textbook Question

When using a terminal alkene under the conditions shown here, explain why it is unnecessary to show the relative stereochemical outcome in the product.

Textbook Question

Which of molecules A–D would you expect to give a positive permanganate test? That is, which would result in a purple KMnO₄ solution turning brown?

(d)

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