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

12. Alcohols, Ethers, Epoxides and Thiols

Alcohol Synthesis

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Alcohol Synthesis

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Problem 15c

Textbook Question

Suggest a reagent and a reactant that could be combined to make each of the following alcohols.
(c)

Verified step by step guidance

Identify the functional groups in the starting material and the product. The starting material has a chlorine atom attached to a carbon chain, indicating it is an alkyl halide. The product has an alcohol group (-OH) in place of the chlorine.

Recognize that the transformation involves replacing the chlorine atom with a hydroxyl group. This suggests a nucleophilic substitution reaction, where the chlorine is replaced by a hydroxide ion.

Consider the type of nucleophilic substitution reaction. Since the starting material is a primary alkyl halide, an SN2 reaction is likely, where a strong nucleophile attacks the carbon attached to the chlorine.

Select a suitable reagent for the nucleophilic substitution. A common choice is sodium hydroxide (NaOH) or potassium hydroxide (KOH), which provides the hydroxide ion (OH⁻) needed for the substitution.

Propose the reaction: Treat the alkyl halide with NaOH or KOH in a suitable solvent, such as water or an alcohol, to facilitate the SN2 reaction and form the desired alcohol product.

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Key Concepts

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

Alcohol Functional Group

Alcohols are organic compounds characterized by the presence of one or more hydroxyl (-OH) groups attached to a carbon atom. Understanding the structure and properties of alcohols is essential for identifying suitable reagents and reactants for their synthesis. The position of the hydroxyl group can significantly influence the reactivity and properties of the alcohol.

Reagents in Organic Synthesis

Reagents are substances that are added to a reaction to cause a chemical change. In the context of synthesizing alcohols, common reagents include reducing agents like lithium aluminum hydride (LiAlH4) or borane (BH3), which can convert carbonyl compounds (like aldehydes or ketones) into alcohols. Knowing the appropriate reagents is crucial for successful alcohol synthesis.

Reaction Mechanisms

Understanding reaction mechanisms is vital for predicting the products of chemical reactions. For alcohol synthesis, mechanisms such as nucleophilic addition or reduction pathways are often involved. Familiarity with these mechanisms helps in selecting the correct reactants and reagents to achieve the desired alcohol structure.

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Related Practice

Textbook Question

Starting from bromobenzene and any other reagents and solvents you need, show how you would synthesize the following compounds. Any of these products may be used as starting materials in subsequent parts of this problem.

a. 1-phenylpropan-1-ol