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

Acid-Catalyzed Hydration

Organic Chemistry

10. Addition Reactions

Acid-Catalyzed Hydration

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3:47 minutes

Problem 14b

Textbook Question

Suggest a reagent to carry out each of the following conversions to an alcohol.
(b)

Verified step by step guidance

Identify the starting material and the target alcohol product. Understanding the structure of both will help in selecting the appropriate reagent.

Consider the functional group present in the starting material. Common functional groups that can be converted to alcohols include alkenes, alkyl halides, carbonyl compounds, and esters.

For alkenes, a common method to convert them to alcohols is through hydroboration-oxidation. This involves using a reagent like borane (BH₃) followed by hydrogen peroxide (H₂O₂) in a basic solution.

If the starting material is an alkyl halide, consider using a nucleophilic substitution reaction with a hydroxide ion (OH⁻) to replace the halide with an alcohol group.

For carbonyl compounds such as ketones or aldehydes, reduction reactions using reagents like sodium borohydride (NaBH₄) or lithium aluminum hydride (LiAlH₄) can convert them to alcohols.

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Key Concepts

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

Reduction Reactions

Reduction reactions in organic chemistry involve the gain of electrons or hydrogen atoms, often converting carbonyl compounds to alcohols. Common reducing agents include lithium aluminum hydride (LiAlH4) and sodium borohydride (NaBH4), which are used to reduce aldehydes, ketones, and esters to their corresponding alcohols.

Functional Group Transformation

Functional group transformation is a key concept in organic synthesis, where one functional group is converted into another. In the context of converting a compound to an alcohol, understanding the nature of the starting material and the appropriate reagent to facilitate this transformation is crucial for successful synthesis.

Reagent Selection

Reagent selection involves choosing the appropriate chemical substance to achieve a desired chemical transformation. Factors influencing this choice include the reactivity of the reagent, the stability of the intermediate, and the specificity of the reaction. For alcohol synthesis, selecting a suitable reducing agent is essential to ensure efficient conversion without side reactions.

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Related Practice

Textbook Question

How can the following compounds be prepared from 3,3-dimethyl-1-butene?

b. 3,3-dimethyl-2-butanol

Textbook Question

In Chapter 8, we learned about the chemistry of terpenes and the interesting reactions they can undergo. One such reaction is the acid-catalyzed conversion of nerol to terpineol. Suggest a mechanism for this transformation

Textbook Question

The acid-catalyzed dehydration we learned in this chapter is reversible, as shown below.

(a) Propose a mechanism for the formation of an alcohol from an alkene.

Textbook Question

The acid-catalyzed dehydration we learned in this chapter is reversible, as shown below.

Textbook Question

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (iii) H₂SO₄ , H₂O . If there is no reaction, write 'no reaction.'

(a)

Textbook Question

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (v) H₂O. If there is no reaction, write 'no reaction.'

(a)

Textbook Question

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (vi) NaOH, H₂O . If there is no reaction, write 'no reaction.'

(a)

Textbook Question

The mechanism of the acid-catalyzed hydration of an alkene to make an alcohol is shown. If this reaction is reversible, draw a mechanism that justifies formation of the alkene from the alcohol under similar conditions. How do you know this mechanism is correct?

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Suggest a reagent to carry out each of the following conversions to an alcohol. (b)

Key Concepts

Reduction Reactions

Functional Group Transformation

Reagent Selection

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Suggest a reagent to carry out each of the following conversions to an alcohol.
(b)