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

Oxymercuration

Organic Chemistry

10. Addition Reactions

Oxymercuration

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2:38 minutes

Problem 59h

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.
(h)

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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 transformation required for the target molecule.

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 requires the formation of an alcohol, hydroboration-oxidation can be used with reagents such as BH₃·THF followed by H₂O₂/NaOH.

Consider the regioselectivity and stereoselectivity of the reaction. For example, hydroboration-oxidation adds an -OH group to the less substituted carbon of the double bond (anti-Markovnikov addition) and occurs with syn stereochemistry.

Write the reaction mechanism to confirm the transformation. Show how the reagent(s) interact with 1-isobutylcyclohexene to produce 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. For example, alkenes, alcohols, and carboxylic acids each have distinct functional groups that influence how they interact with other substances.

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 transformations of functional groups, such as oxidation, reduction, or substitution. Knowing the appropriate reagents for specific transformations is crucial for synthesizing desired products from starting materials.

Reaction Mechanisms

Reaction mechanisms describe the step-by-step process by which reactants are converted into products. Understanding these mechanisms helps predict the outcome of reactions and the conditions required for them to occur. For instance, knowing whether a reaction proceeds via an electrophilic addition or a nucleophilic substitution can guide the choice of reagents and conditions needed to achieve the desired transformation.

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Related Practice

Textbook Question

Predict the products you would get when the following alkenes react under the following conditions: (ii) 1. Hg(OAc)₂ , H₂O , 2. NaBH₄

(a)

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (v) 1. Hg(OAc)₂ , H₂O 2. NaBH₄

(g)

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (v) 1. Hg(OAc)₂ , H₂O 2. NaBH₄

(k)

Textbook Question

Would you expect the following to produce an equal or unequal mixture of stereoisomers?

(a)

Textbook Question

For the alkynes shows here, show the product(s) expected to form when treated under the following conditions: (vi) H₂SO₄, HgSO₄, H₂O. If you expect two products, show both.

(c)

Textbook Question

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (ii) 1. Hg(OAc)₂ 2. NaBH₄.If there is no reaction, write 'no reaction.'

(a)

Textbook Question

Predict the product of the following aldehyde/ketone syntheses.

(d)

Textbook Question

Would you expect the following to produce an equal or unequal mixture of stereoisomers?

(c)

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