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

Imine vs Enamine

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

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1:39 minutes

Problem 43

Textbook Question

Explain why acetals do not react with nucleophiles.

Verified step by step guidance

Acetals are compounds that contain two alkoxy groups (-OR) attached to the same carbon atom, which is also bonded to a hydrogen atom or another carbon atom. This structure makes acetals relatively stable under neutral or basic conditions.

The carbon atom in an acetal is fully saturated (sp³ hybridized) and does not possess a partial positive charge. This is because the electron-donating alkoxy groups stabilize the carbon atom, reducing its electrophilicity.

Nucleophiles are species that donate electron pairs to electrophilic centers. Since the carbon atom in an acetal is not electrophilic, it does not attract nucleophiles effectively.

Additionally, acetals are stable under basic conditions and do not undergo hydrolysis or other reactions unless exposed to acidic conditions. Acidic conditions can protonate one of the alkoxy groups, making the carbon atom more electrophilic and susceptible to nucleophilic attack.

In summary, acetals do not react with nucleophiles because their carbon atom is not electrophilic due to the electron-donating effects of the alkoxy groups, and they are stable under neutral or basic conditions.

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Key Concepts

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

Acetal Structure

Acetals are formed from the reaction of an aldehyde or ketone with an alcohol in the presence of an acid catalyst. They consist of a carbon atom bonded to two alkoxy groups (–OR) and a hydrogen atom or another carbon atom. This structure stabilizes the carbon atom, making it less electrophilic and less susceptible to nucleophilic attack.

Nucleophilicity

Nucleophiles are species that donate an electron pair to form a chemical bond. They are typically attracted to positively charged or electron-deficient centers. In the case of acetals, the carbon atom is not electron-deficient due to the presence of the two electron-donating alkoxy groups, which reduces its reactivity towards nucleophiles.

Stability of Acetals

Acetals are generally stable under neutral or basic conditions and do not readily undergo hydrolysis or react with nucleophiles. This stability arises from the strong C–O bonds in the acetal structure and the steric hindrance provided by the bulky alkoxy groups, which further protect the carbon center from nucleophilic attack.

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