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

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Problem 1b

Textbook Question

In each case, circle the stronger nucleophile.
(b)

Verified step by step guidance

Step 1: Understand the concept of nucleophilicity. Nucleophilicity refers to the ability of a species to donate a pair of electrons to an electrophile. It is influenced by factors such as charge, electronegativity, steric hindrance, and the solvent used.

Step 2: Compare the electronegativity of the atoms involved. Oxygen (in -OH) is more electronegative than nitrogen (in -NH2), meaning oxygen holds onto its electrons more tightly, making it less likely to donate them compared to nitrogen.

Step 3: Consider the lone pair availability. Nitrogen in -NH2 has a lone pair of electrons that is less tightly held due to its lower electronegativity, making it a stronger nucleophile compared to oxygen in -OH.

Step 4: Evaluate the steric hindrance. Both -OH and -NH2 groups are similar in size and steric hindrance, so this factor does not significantly affect their nucleophilicity in this comparison.

Step 5: Conclude based on the above factors. Nitrogen in -NH2 is the stronger nucleophile compared to oxygen in -OH due to its lower electronegativity and greater ability to donate electrons.

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Key Concepts

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

Nucleophilicity

Nucleophilicity refers to the ability of a species to donate an electron pair to an electrophile during a chemical reaction. Stronger nucleophiles are more reactive and can more readily form bonds with electrophiles. Factors influencing nucleophilicity include charge, electronegativity, and steric hindrance.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In this case, the hydroxyl group (–OH) and the amino group (–NH2) are functional groups that influence the nucleophilicity of the compounds they are part of, with the amino group generally being a stronger nucleophile.

Basicity and Nucleophilicity Relationship

Basicity and nucleophilicity are related concepts, as both involve the donation of electron pairs. However, basicity refers to the ability to accept protons (H+), while nucleophilicity focuses on the ability to donate electrons to electrophiles. Generally, stronger bases are also stronger nucleophiles, but this is not always the case due to steric and solvent effects.

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Related Practice

Textbook Question

In each case, circle the stronger nucleophile.

(c)

Textbook Question

Provide a reasonable arrow-pushing mechanism for the following Lewis acid–Lewis base reactions.

(a)

Textbook Question

Provide an arrow-pushing mechanism for the following hypothetical base half-reactions.

(b)

Textbook Question

BCl₃ has an empty p orbital, so it is a strong Lewis acid. Would you expect an amide to react with BCl₃ at nitrogen or oxygen?

Textbook Question

Based on the analysis you used in Assessment 17.3, which carbonyl would you expect to react most quickly with a nucleophile?

(c)

Textbook Question

Classify the following nucleophiles as strong, weak, or intermediate. Would you expect each to add to a carbonyl directly or wait for a carbocation to form?

Textbook Question

Would you expect a ketone or an ester to be more reactive with a strong nucleophile? Justify your answer.

Textbook Question

Rank the reactivity of the following carbonyls with nucleophiles, from least reactive to most reactive.

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