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 Protecting Group

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Acetal Protecting Group

Previous problemNext problem

5:10 minutes

Problem 68b

Textbook Question

One of these reacts with dilute aqueous acid and the other does not. Give a mechanism for the one that reacts, and show why this mechanism does not work for the other one.
(b)

Verified step by step guidance

Identify the functional groups present in both compounds. Look for groups that are known to react with dilute aqueous acid, such as esters, amides, or epoxides.

Determine the reactivity of each functional group with dilute aqueous acid. For example, esters can undergo hydrolysis in the presence of acid, while amides are generally more resistant.

For the compound that reacts, propose a mechanism. If it is an ester, the mechanism involves protonation of the carbonyl oxygen, followed by nucleophilic attack by water, leading to the formation of a tetrahedral intermediate.

Explain why the mechanism does not work for the other compound. If the other compound is an amide, discuss the resonance stabilization of the amide bond, which makes it less susceptible to acid-catalyzed hydrolysis.

Illustrate the complete mechanism for the reacting compound, showing each step with curved arrows to indicate electron movement, and highlight the key differences in structure or stability that prevent the reaction in the non-reacting compound.

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.

Acid-Base Reactions

Acid-base reactions involve the transfer of protons (H+) between reactants. In organic chemistry, understanding how different functional groups interact with acids is crucial. For example, alcohols can react with acids to form alkyl halides through protonation, while other groups, like alkenes, may not undergo the same reaction due to their structural characteristics.

Reaction Mechanisms

A reaction mechanism outlines the step-by-step process by which reactants transform into products. It includes details about bond breaking and forming, intermediates, and transition states. For the compound that reacts with dilute aqueous acid, the mechanism may involve protonation followed by nucleophilic attack, while the non-reacting compound may lack a suitable site for protonation or nucleophilic attack.

Functional Group Reactivity

Different functional groups exhibit varying reactivities based on their electronic and steric properties. For instance, alcohols are generally more reactive towards acids than alkenes due to their ability to form stable carbocations. Understanding the specific functional groups present in the compounds in question is essential to predict their behavior in acid reactions.

Watch next

Master Protecting Groups with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

One of these reacts with dilute aqueous acid and the other does not. Give a mechanism for the one that reacts, and show why this mechanism does not work for the other one.

(a)

Textbook Question

Predict the major products of the following reactions:

(d)

Textbook Question

Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.

(d)

Textbook Question

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

(d)

Textbook Question

Rationalize the difference in Kₑq for the following reactions. Be sure to account for both ∆S and ∆H.

1. Analyze ∆S and ∆H differences." width="737">

Open Question

Provide the chemical steps necessary for the following synthesis.

Open Question

Provide the chemical steps necessary for the following synthesis.

Textbook Question

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

(b)

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap

One of these reacts with dilute aqueous acid and the other does not. Give a mechanism for the one that reacts, and show why this mechanism does not work for the other one.(b)

Key Concepts

Acid-Base Reactions

Reaction Mechanisms

Functional Group Reactivity

Watch next

One of these reacts with dilute aqueous acid and the other does not. Give a mechanism for the one that reacts, and show why this mechanism does not work for the other one.
(b)