1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 19m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 18m
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 Acids3h 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

18. Aromaticity

Acidity of Aromatic Hydrocarbons

Organic Chemistry

18. Aromaticity

Acidity of Aromatic Hydrocarbons

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7:28 minutes

Problem 15Bruice - 8th Edition

Textbook Question

Rank the following amides from greatest reactivity to least reactivity toward acid-catalyzed hydrolysis: A.
B.
C.

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Identify the substituents on the nitrogen atom of each amide: A has a cyclohexyl group, B has a nitrophenyl group, and C has a methylphenyl group.

Consider the electron-withdrawing or electron-donating effects of these substituents: the nitro group in B is a strong electron-withdrawing group, while the methyl group in C is a weak electron-donating group.

Recall that electron-withdrawing groups increase the reactivity of amides towards acid-catalyzed hydrolysis by stabilizing the transition state.

Rank the amides based on the electron-withdrawing ability of their substituents: B (strong electron-withdrawing) > A (neutral) > C (electron-donating).

Conclude that the order of reactivity from greatest to least is B > A > C.

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Key Concepts

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

Amide Reactivity

Amides are generally less reactive than other carbonyl compounds due to the resonance stabilization provided by the nitrogen atom. The lone pair of electrons on the nitrogen can delocalize into the carbonyl group, reducing the electrophilicity of the carbonyl carbon. Understanding the factors that influence amide reactivity, such as steric hindrance and electronic effects, is crucial for predicting their behavior in reactions like acid-catalyzed hydrolysis.

Electronic Effects

The electronic environment around the carbonyl group significantly affects the reactivity of amides. Electron-withdrawing groups, such as nitro groups, increase the electrophilicity of the carbonyl carbon, making the amide more reactive. Conversely, electron-donating groups can decrease reactivity by stabilizing the carbonyl through resonance. Analyzing the substituents on the amides in the question helps determine their relative reactivity in hydrolysis.

Steric Hindrance

Steric hindrance refers to the crowding around a reactive site that can impede the approach of reactants. In the context of amides, bulky substituents near the carbonyl group can hinder the access of water molecules during acid-catalyzed hydrolysis, thus reducing reactivity. Evaluating the steric effects of the substituents in the given amides is essential for ranking their reactivity accurately.