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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2:06 minutes

Problem 55

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 their reactivity toward nucleophilic addition, considering both electronic and steric factors. Typically, the order of reactivity is: aldehydes > ketones > esters > amides, but this can vary depending on specific substituents.

Verify your ranking by considering resonance effects or other stabilizing interactions that might influence the reactivity of the carbonyl group in each compound.

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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 center, typically a carbon atom in a carbonyl group. This reaction is crucial for forming new carbon-carbon or carbon-heteroatom bonds. The reactivity of compounds toward nucleophilic addition depends on the electrophilicity of the carbonyl carbon, which is influenced by factors such as steric hindrance and electronic effects.

Electrophilicity

Electrophilicity refers to the tendency of a chemical species to accept electrons, making it a target for nucleophiles. In the context of carbonyl compounds, the more positive the carbonyl carbon is, the more reactive it is toward nucleophilic attack. Factors that enhance electrophilicity include the presence of electron-withdrawing groups and the overall stability of the molecule, which can affect the carbonyl's susceptibility to nucleophiles.

Steric Hindrance

Steric hindrance is the prevention of chemical reactions due to the spatial arrangement of atoms within a molecule. In nucleophilic addition reactions, bulky substituents around the electrophilic center can impede the approach of nucleophiles, thereby decreasing reactivity. Understanding steric effects is essential for predicting the reactivity of various carbonyl compounds, as more sterically hindered compounds are generally less reactive toward nucleophilic addition.

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