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

Imine vs Enamine

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

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2:38 minutes

Problem 39(4)

Textbook Question

Which of the following are a. hemiacetals? b. acetals? c. hydrates?
4.

Verified step by step guidance

Step 1: Understand the definitions of the terms provided in the question. A hemiacetal contains one hydroxyl group (-OH) and one alkoxy group (-OR) attached to the same carbon atom. An acetal contains two alkoxy groups (-OR) attached to the same carbon atom. A hydrate contains two hydroxyl groups (-OH) attached to the same carbon atom.

Step 2: Analyze the given chemical structure (CH3)2C(OH)2. This molecule has two hydroxyl groups (-OH) attached to the same carbon atom, which matches the definition of a hydrate.

Step 3: Compare the structure to the definitions of hemiacetals and acetals. Since the molecule does not contain any alkoxy groups (-OR), it cannot be classified as a hemiacetal or an acetal.

Step 4: Confirm the classification of the molecule as a hydrate based on the presence of two hydroxyl groups (-OH) attached to the same carbon atom.

Step 5: Conclude that the molecule (CH3)2C(OH)2 is a hydrate and does not fall under the categories of hemiacetals or acetals.

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Key Concepts

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

Hemiacetals

Hemiacetals are formed when an aldehyde or ketone reacts with an alcohol, resulting in a compound that contains both an alcohol (-OH) and an ether (-O-) functional group. They typically exist in equilibrium with their corresponding carbonyl compounds and are characterized by having one -OH group and one -OR group attached to the same carbon atom.

Acetals

Acetals are derived from hemiacetals through a reaction with an additional alcohol, leading to a compound with two -OR groups attached to the same carbon atom. This transformation involves the loss of water and is significant in organic synthesis, as acetals are often more stable than their hemiacetal precursors and can serve as protecting groups for carbonyl functionalities.

Hydrates

Hydrates are formed when water adds to a carbonyl compound, such as an aldehyde or ketone, resulting in a molecule that contains two -OH groups attached to the same carbon atom. This process is reversible and is important in various biochemical pathways, as it can influence the reactivity and stability of carbonyl compounds in aqueous environments.

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

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Textbook Question

LOOKING AHEAD CHAPTERS 8, 17 In Chapters 8 and 17 we learn two reaction for the synthesis of the alcohol shown. (a) Show a mechanism for each of the reactions. (b) If you were designing a synthetic route, which would be considered more sustainable? Consider all factors. [Assume the starting organic molecules are equally green.]

Textbook Question

Rank the following compounds from largest K_eq to smallest K_eq for hydrate formation:

Textbook Question

Can the rate of hydrate formation be increased by hydroxide ion as well as by acid? Explain.

Textbook Question

Rank the following carbonyl compounds in order of increasing equilibrium constant for hydration:

CH₃COCH₂Cl ClCH₂CHO CH₂O CH₃COCH₃ CH₃CHO