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

Ranking Acidity

Organic Chemistry

3. Acids and Bases

Ranking Acidity

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3:07 minutes

Problem 34c,d

Textbook Question

For each of the following compounds, indicate the atom that is protonated when an acid is added to a solution of the compound.
c.
d.

Verified step by step guidance

Step 1: Analyze the structure of compound A. It contains a carbonyl group (C=O) and an ether oxygen atom. The ether oxygen has lone pairs of electrons, making it a likely site for protonation when an acid is added.

Step 2: Consider the structure of compound B. It contains a carbonyl group (C=O) and an amine group (-NH). The nitrogen atom in the amine group has lone pairs of electrons, making it a likely site for protonation when an acid is added.

Step 3: Recall that protonation occurs at the atom with the highest electron density or lone pairs that can interact with the proton (H⁺). In compound A, the ether oxygen is the most likely site for protonation due to its lone pairs.

Step 4: In compound B, the nitrogen atom in the amine group is the most likely site for protonation because nitrogen is more basic than oxygen and readily accepts a proton.

Step 5: Summarize the findings: For compound A, the ether oxygen is protonated. For compound B, the nitrogen in the amine group is protonated.

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Key Concepts

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

Protonation

Protonation is the addition of a proton (H⁺) to a molecule, which can significantly alter its chemical properties. In organic chemistry, this process often occurs in the presence of acids, where the proton attaches to a site on the molecule that has a lone pair of electrons, typically resulting in a positively charged species. Understanding which atom is protonated helps predict the behavior of the compound in reactions.

Acid-Base Chemistry

Acid-base chemistry involves the transfer of protons between species, where acids donate protons and bases accept them. This concept is fundamental in organic reactions, as the nature of the acid and the basicity of the functional groups in the compounds dictate the site of protonation. Recognizing the acidic and basic sites in a molecule is crucial for predicting the outcome of acid-base reactions.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the context of the provided compounds, identifying functional groups such as alcohols, amines, or carbonyls is essential, as they influence the site of protonation. Each functional group has distinct properties that determine its reactivity in acid-base chemistry.

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Related Practice

Textbook Question

Ethanol, methylamine, and acetic acid are all amphoteric, reacting as either acids or bases depending on the conditions.

b. Rank ethanol, methylamine, and acetic acid in decreasing order of basicity. In each case, show the equation for the reaction with a generic acid (HA) to give the conjugate acid.

Textbook Question

Ethanol, methylamine, and acetic acid are all amphoteric, reacting as either acids or bases depending on the conditions.

a. Rank ethanol, methylamine, and acetic acid in decreasing order of acidity. In each case, show the equation for the reaction with a generic base (B:⁻) to give the conjugate base.

Textbook Question

Which is a stronger acid?

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d. CH₃CH₂CH₂OH or CH₃CH₂CH₂SH

Textbook Question

Which is a stronger acid?

Textbook Question

For each of the following compounds, indicate the atom that is protonated when an acid is added to a solution of the compound.

Textbook Question

Rank the carbanions shown in the margin from most basic to least basic.

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Textbook Question