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

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

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4:11 minutes

Problem 57a(6)

Textbook Question

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

Verified step by step guidance

Step 1: Identify the starting material and the product. The starting material is an aldehyde (ethanal, CH₃CHO), and the product is a primary alcohol (ethanol, CH₃CH₂OH).

Step 2: Recognize the type of reaction. This is a reduction reaction where the aldehyde is reduced to a primary alcohol.

Step 3: Select the appropriate reducing agent. Common reducing agents for this transformation include sodium borohydride (NaBH₄) or lithium aluminum hydride (LiAlH₄).

Step 4: Consider the reaction conditions. NaBH₄ is typically used in protic solvents like ethanol or water, while LiAlH₄ requires anhydrous conditions and is often used in ether solvents such as diethyl ether.

Step 5: Write the reaction mechanism. The reducing agent donates hydride ions (H⁻) to the carbonyl carbon of the aldehyde, breaking the C=O double bond and forming the primary alcohol.

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Key Concepts

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

Carbonyl Compounds

Carbonyl compounds contain a carbon atom double-bonded to an oxygen atom (C=O). They are classified into aldehydes and ketones, depending on the carbonyl's position in the molecule. Aldehydes, like the one shown in the reaction, have at least one hydrogen atom attached to the carbonyl carbon, making them more reactive in nucleophilic addition reactions.

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, such as that in a carbonyl group. This reaction typically leads to the formation of alcohols when the carbonyl compound is reduced. In the context of the question, a nucleophile will add to the carbonyl carbon, resulting in the formation of a primary alcohol.

Reagents for Alcohol Formation

To convert a carbonyl compound into a primary alcohol, specific reagents are required. Commonly, lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4) are used as reducing agents. These reagents donate hydride ions (H-) to the carbonyl carbon, effectively reducing it and resulting in the formation of a primary alcohol.

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Related Practice

Textbook Question

Using bromocyclohexane as a starting material, how could you synthesize the following compounds?

Textbook Question

How can the following compounds be prepared from the given starting materials?

Textbook Question

Show how each of the following compounds can be prepared, using the given starting material:

Textbook Question

Identify A through O:

Textbook Question

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

Textbook Question

Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.

(c)

Textbook Question

Predict the major products of the following reactions.

(d)

Textbook Question

Two of the methods for converting alkyl halides to carboxylic acids are covered in Sections 20-8B and 20-8C. One is formation of a Grignard reagent followed by addition of carbon dioxide and then dilute acid. The other is substitution by cyanide ion, followed by hydrolysis of the resulting nitrile. For each of the following conversions, decide whether either or both of these methods would work, and explain why. Show the reactions you would use.

(a)

(b)

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