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

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Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

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2:35 minutes

Problem 49e

Textbook Question

For each compound,
1. name the functional group.
2. show what compound(s) result from complete hydrolysis.
(e)

Verified step by step guidance

Step 1: Identify the functional group in the compound. The structure contains a cyclic ester functional group, which is known as a lactone. Lactones are cyclic esters formed by the intramolecular reaction of a hydroxy acid.

Step 2: Understand the concept of hydrolysis. Hydrolysis of esters involves breaking the ester bond using water, typically under acidic or basic conditions, resulting in the formation of an alcohol and a carboxylic acid.

Step 3: Analyze the structure of the lactone. The cyclic ester bond will break during hydrolysis, leading to the formation of a linear compound. The oxygen atom in the ester bond will form part of the alcohol group, while the carbonyl carbon will form the carboxylic acid group.

Step 4: Predict the products of hydrolysis. For this lactone, hydrolysis will yield a hydroxy acid. Specifically, the ring will open, and the hydroxyl group (-OH) will attach to the carbon that was part of the ester oxygen, while the carbonyl group will form a carboxylic acid (-COOH).

Step 5: Write the general reaction for hydrolysis. The lactone reacts with water to produce a hydroxy acid. The chemical equation can be represented as:

R_{1} (CO) R_{2} (O) + H O_{2} \to R_{1} (COOH) R_{2} (OH)

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Key Concepts

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

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. They determine the properties and reactivity of organic compounds. Common functional groups include hydroxyl (-OH), carboxyl (-COOH), and amine (-NH2), each imparting distinct behaviors to the compounds they are part of.

Hydrolysis

Hydrolysis is a chemical reaction in which water is used to break down a compound. In organic chemistry, it often involves the cleavage of bonds in larger molecules, resulting in smaller molecules or functional groups. Complete hydrolysis typically refers to the full breakdown of a compound into its constituent parts, such as converting esters into acids and alcohols.

Naming Organic Compounds

Naming organic compounds follows the IUPAC (International Union of Pure and Applied Chemistry) nomenclature rules, which provide a systematic way to name compounds based on their structure. This includes identifying the longest carbon chain, the presence of functional groups, and the position of substituents. Proper naming is essential for clear communication in chemistry.

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Textbook Question

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

(b) excess CH₃OH, H⁺

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

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.

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.

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For each compound,1. name the functional group.2. show what compound(s) result from complete hydrolysis.(e)

Key Concepts

Functional Groups

Hydrolysis

Naming Organic Compounds

Watch next

For each compound,
1. name the functional group.
2. show what compound(s) result from complete hydrolysis.
(e)