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

Previous problemNext problem

2:48 minutes

Problem 57a(9)

Textbook Question

a. Show the reagents required to form the primary alcohol in each of the following reactions.

Verified step by step guidance

Identify the starting material and the product. The starting material is 1-bromobutane (C4H9Br), and the product is 1-butanol (C4H9OH), a primary alcohol.

Recognize that the transformation involves replacing the bromine atom (Br) with a hydroxyl group (OH). This is a nucleophilic substitution reaction.

Determine the type of nucleophilic substitution. Since the substrate is a primary alkyl halide, the reaction will proceed via the SN2 mechanism.

Select an appropriate nucleophile and solvent. Use hydroxide ion (OH⁻) as the nucleophile, which can be provided by a strong base like sodium hydroxide (NaOH) or potassium hydroxide (KOH). The reaction is typically carried out in an aqueous or aqueous-alcoholic solvent.

Write the reaction conditions: Heat the reaction mixture to promote the substitution reaction, as SN2 reactions often require mild heating to proceed efficiently.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophilic carbon atom, replacing a leaving group. In this case, the bromide (Br) acts as the leaving group, and the hydroxide ion (OH-) serves as the nucleophile, leading to the formation of a primary alcohol.

Reagents for Alcohol Formation

To convert an alkyl halide to an alcohol, specific reagents are required. For the reaction shown, the hydroxide ion (OH-) is typically provided by a strong base such as sodium hydroxide (NaOH) or potassium hydroxide (KOH). These reagents facilitate the nucleophilic attack on the carbon atom bonded to the bromine.

Primary Alcohols

Primary alcohols are characterized by having the hydroxyl (-OH) group attached to a carbon atom that is bonded to only one other carbon atom. This structure influences their reactivity and properties, making them distinct from secondary and tertiary alcohols. Understanding the structure of primary alcohols is essential for predicting their behavior in chemical reactions.

Watch next

Master Forming alcohols through Oxymercuration-Reduction. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Show how you would synthesize the following alcohol from appropriate alkene.

(a)

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

Textbook Question

Predict the product of each of the following alcohol synthesis reactions.

(b)

Textbook Question

Show a mechanism for each of the alcohol synthesis reactions in Table 13.8.

<IMAGE>

Textbook Question

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

(c)

Textbook Question

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