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

3. Acids and Bases

Reaction Mechanism

Organic Chemistry

3. Acids and Bases

Reaction Mechanism

Previous problemNext problem

2:48 minutes

Problem 61c

Textbook Question

Would you expect the following species to be electrophiles or nucleophiles? Some may be both. Explain your answer.
(c)

Verified step by step guidance

Step 1: Begin by understanding the definitions of electrophiles and nucleophiles. Electrophiles are species that are electron-deficient and can accept a pair of electrons, often having a positive charge or partial positive charge. Nucleophiles are species that are electron-rich and can donate a pair of electrons, often having a negative charge or lone pairs of electrons.

Step 2: Examine the structure and composition of the given species (c). Look for features such as lone pairs, negative charges, or electron-rich regions to determine nucleophilic behavior. Similarly, look for positive charges, partial positive charges, or electron-deficient regions to determine electrophilic behavior.

Step 3: Consider resonance effects, inductive effects, and hybridization of the atoms in the species. These factors can influence the electron density and determine whether the species acts as an electrophile or nucleophile. For example, resonance can delocalize electron density, affecting reactivity.

Step 4: Evaluate whether the species can act as both an electrophile and a nucleophile. Some species may have regions that are electron-rich (nucleophilic) and regions that are electron-deficient (electrophilic). For example, a molecule with a lone pair and a positive charge could exhibit dual behavior.

Step 5: Summarize your findings by explaining the reasoning behind the classification of the species as an electrophile, nucleophile, or both. Use the structural and electronic features of the species to justify your conclusion.

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.

Electrophiles

Electrophiles are species that are electron-deficient and seek to accept electrons from nucleophiles during chemical reactions. They typically have a positive charge or a partial positive charge due to electronegative atoms. Common examples include carbocations and carbonyl compounds, which can react with nucleophiles to form new bonds.

Nucleophiles

Nucleophiles are electron-rich species that donate an electron pair to electrophiles in a chemical reaction. They often possess a negative charge or have lone pairs of electrons available for bonding. Examples include anions like hydroxide (OH-) and neutral molecules like ammonia (NH3), which can attack electrophilic centers.

Dual Reactivity

Some species can act as both electrophiles and nucleophiles depending on the reaction conditions and the other reactants involved. For instance, a molecule with both a nucleophilic site (like a lone pair) and an electrophilic site (like a carbonyl) can participate in different types of reactions, showcasing its versatility in organic chemistry.

Watch next

Master How to tell if a molecule will be reactive or not. with a bite sized video explanation from Johnny

Start learning