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

21. Aldehydes and Ketones: Nucleophilic Addition

Acetal

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Acetal

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1:50 minutes

Problem 61a

Textbook Question

There are three dioxane isomers: 1,2-dioxane, 1,3-dioxane, and 1,4-dioxane. One of these acts like an ether and is an excellent solvent for Grignard reactions. Another one is potentially explosive when heated. The third one quickly hydrolyzes in dilute acid. Show which isomer acts like a simple ether, and then explain why one of them is potentially explosive.

Verified step by step guidance

Identify the structural differences between the three dioxane isomers: 1,2-dioxane, 1,3-dioxane, and 1,4-dioxane. These isomers differ in the position of the oxygen atoms in the six-membered ring.

Consider the chemical properties of ethers. Ethers are generally stable and do not react easily, making them good solvents for Grignard reactions. The isomer that acts like a simple ether will have a structure that minimizes strain and reactivity.

Analyze the stability of each isomer. 1,4-dioxane is the most stable due to its symmetrical structure, which reduces ring strain and makes it behave like a simple ether. This stability makes it an excellent solvent for Grignard reactions.

Examine the potential explosiveness of the isomers. 1,2-dioxane is potentially explosive when heated due to its high ring strain and the presence of two adjacent oxygen atoms, which can lead to peroxide formation.

Consider the hydrolysis of the isomers in dilute acid. 1,3-dioxane quickly hydrolyzes in dilute acid because the oxygen atoms are positioned to facilitate ring opening, making it less stable compared to the other isomers.

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Key Concepts

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

Dioxane Isomers

Dioxane isomers refer to the three structural variations of dioxane, which differ in the positioning of the oxygen atoms within the six-membered ring. The isomers are 1,2-dioxane, 1,3-dioxane, and 1,4-dioxane. Each isomer exhibits distinct chemical properties and reactivity, influencing their behavior in reactions, such as their role as solvents or their stability under heat.

Grignard Reactions

Grignard reactions involve the use of Grignard reagents, which are organomagnesium compounds that react with electrophiles to form carbon-carbon bonds. The choice of solvent is crucial, as it must not react with the Grignard reagent. 1,3-dioxane acts like a simple ether and is an excellent solvent for these reactions due to its ability to stabilize the Grignard reagent without participating in the reaction.

Explosive Potential of 1,4-Dioxane

1,4-Dioxane can be potentially explosive when heated due to its ability to form peroxides, which are highly reactive and can decompose violently. The presence of oxygen atoms in the cyclic structure can lead to the formation of these unstable peroxide compounds, especially when exposed to heat or light, making it necessary to handle this isomer with caution.

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Related Practice

Textbook Question

Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.

(d) excess ethanol and acid

Textbook Question

Alcohols combine with ketones and aldehydes to form interesting derivatives, which we will discuss in Chapter 18. The following reactions show the hydrolysis of two such derivatives. Propose mechanisms for these reactions.

(a)

Textbook Question

For each compound,

1. name the functional group.

2. show what compound(s) result from complete hydrolysis.

(d)

Textbook Question

For each compound,

1. name the functional group.

2. show what compound(s) result from complete hydrolysis.

(e)

Textbook Question

There are three dioxane isomers: 1,2-dioxane, 1,3-dioxane, and 1,4-dioxane. One of these acts like an ether and is an excellent solvent for Grignard reactions. Another one is potentially explosive when heated. The third one quickly hydrolyzes in dilute acid. Propose a mechanism for the acid hydrolysis of the third isomer.

Textbook Question

Simple aminoacetals hydrolyze quickly and easily in dilute acid. Propose a mechanism for hydrolysis of the following aminoacetal:

Textbook Question

Hydration of an aldehyde is also catalyzed by hydroxide ion. Propose a mechanism for the reaction.

Textbook Question

Which of the following are a. hemiacetals? b. acetals? c. hydrates?

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