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

Nucleophilic Addition

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Nucleophilic Addition

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4:07 minutes

Problem 71

Textbook Question

Rank the following compounds from most reactive to least reactive toward nucleophilic addition:

Verified step by step guidance

Identify the functional groups present in each compound. Nucleophilic addition reactions typically occur at carbonyl groups (C=O), so focus on compounds containing aldehydes, ketones, esters, or other carbonyl-containing groups.

Consider the electronic effects of substituents attached to the carbonyl carbon. Electron-withdrawing groups (e.g., halogens, nitro groups) increase the electrophilicity of the carbonyl carbon, making it more reactive toward nucleophiles. Electron-donating groups (e.g., alkyl groups) decrease electrophilicity, reducing reactivity.

Evaluate steric hindrance around the carbonyl carbon. Compounds with less steric hindrance (e.g., aldehydes) are generally more reactive than those with more steric hindrance (e.g., ketones or bulky esters).

Rank the compounds based on the combined effects of electronic and steric factors. Aldehydes are typically more reactive than ketones, which are more reactive than esters or amides. Within each category, consider the specific substituents to refine the ranking.

Verify the ranking by considering resonance effects or other stabilizing interactions that might influence the reactivity of the carbonyl group. For example, conjugation with an aromatic ring can reduce reactivity by delocalizing the positive charge on the carbonyl carbon.

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Key Concepts

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

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophilic carbon atom, typically in carbonyl compounds. This process is crucial for forming new bonds and is influenced by the electrophilicity of the carbonyl carbon, which is affected by the substituents attached to it. Understanding the mechanism and factors that enhance or diminish reactivity is essential for ranking compounds.

Electrophilicity

Electrophilicity refers to the tendency of a molecule to attract electrons, making it susceptible to nucleophilic attack. In the context of carbonyl compounds, the presence of electron-withdrawing groups increases the electrophilicity of the carbonyl carbon, enhancing its reactivity. Conversely, electron-donating groups can decrease electrophilicity, making the compound less reactive toward nucleophiles.

Steric Hindrance

Steric hindrance is the repulsion that occurs when atoms are brought close together, which can impede the approach of nucleophiles to the electrophilic center. In nucleophilic addition reactions, bulky substituents around the carbonyl group can create steric barriers, reducing the reactivity of the compound. Evaluating steric effects is crucial when ranking compounds based on their reactivity toward nucleophilic addition.

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