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 12b

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?
b)

Verified step by step guidance

Step 1: Analyze the structure of the nucleophile provided in the image. The molecule shown is a carboxylic acid, which contains a carbonyl group (C=O) and a hydroxyl group (-OH) attached to the same carbon.

Step 2: Evaluate the nucleophilicity of the molecule. Carboxylic acids are generally weak nucleophiles because the oxygen atoms are involved in resonance stabilization, reducing their availability to donate electrons.

Step 3: Consider the reactivity of the nucleophile with a carbonyl group. Weak nucleophiles typically do not add directly to a carbonyl group unless the carbonyl is activated (e.g., by protonation or the formation of a carbocation).

Step 4: Determine whether the nucleophile would wait for a carbocation to form. In this case, the carboxylic acid would likely require activation of the carbonyl group before it can react, as its nucleophilicity is insufficient for direct addition.

Step 5: Classify the nucleophile. Based on the analysis, the carboxylic acid is classified as a weak nucleophile, and it would wait for a carbocation or an activated carbonyl to form before reacting.

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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, such as a carbonyl carbon. Strong nucleophiles are typically negatively charged or have lone pairs that can readily participate in reactions, while weak nucleophiles are neutral or less reactive. Understanding the strength of nucleophiles is crucial for predicting their behavior in reactions involving carbonyl compounds.

Carbonyl Chemistry

Carbonyl compounds, characterized by a carbon-oxygen double bond, are key functional groups in organic chemistry. They can undergo nucleophilic addition reactions where nucleophiles attack the electrophilic carbon atom. The reactivity of carbonyls is influenced by the nature of the substituents attached to the carbonyl carbon, which can stabilize or destabilize the transition state during nucleophilic attack.

Carbocation Stability

Carbocations are positively charged carbon species that can form during certain organic reactions, particularly when a leaving group departs. The stability of a carbocation is influenced by its degree (primary, secondary, tertiary) and the presence of electron-donating groups. Understanding carbocation stability is essential for predicting whether a nucleophile will add directly to a carbonyl or wait for a carbocation to form, as more stable carbocations are more likely to form and react.

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Related Practice

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

In each case, circle the stronger nucleophile.

(b)

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

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.

Textbook Question

The following reaction steps are shown using conventional electron pushing. (a) Draw the second product whose formation would have been rationalized with this same arrow.

(a)

Textbook Question

The following reaction steps are shown using conventional electron pushing. (b) Use the bouncing arrow formalism to illustrate the formation of only the product shown.

(a)

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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?b)

Key Concepts

Nucleophilicity

Carbonyl Chemistry

Carbocation Stability

Watch next

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?
b)