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

Acids and Bases

Organic Chemistry

3. Acids and Bases

Acids and Bases

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2:41 minutes

Problem 20b(i,ii,iii)

Textbook Question

In the following reactions,
(i) identify the acid and base,
(ii) identify the most electron-rich atom in the base,
(iii) identify the most acidic hydrogen in the acid,
(b)

Verified step by step guidance

Step 1: Identify the acid and base in the reaction. Ethylamide contains a nitrogen atom with a lone pair of electrons, making it a potential base. Propan-2-ol contains an -OH group, which can donate a proton (H⁺), making it the acid in this reaction.

Step 2: Determine the most electron-rich atom in the base. In ethylamide, the nitrogen atom is the most electron-rich due to its lone pair of electrons, which makes it capable of accepting a proton.

Step 3: Identify the most acidic hydrogen in the acid. In propan-2-ol, the hydrogen atom attached to the oxygen in the -OH group is the most acidic because the oxygen atom is electronegative and stabilizes the negative charge formed after losing the proton.

Step 4: Analyze the reaction mechanism. The nitrogen atom in ethylamide (base) will use its lone pair to attack the acidic hydrogen of propan-2-ol (acid), leading to the formation of a conjugate acid and conjugate base.

Step 5: Consider the equilibrium. The reaction will establish an equilibrium between the acid-base pairs, and the position of equilibrium will depend on the relative strengths of the acid and base involved.

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Key Concepts

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

Acids and Bases

In organic chemistry, acids are substances that can donate a proton (H+), while bases are substances that can accept a proton. This concept is fundamental for understanding acid-base reactions, where the transfer of protons occurs between the acid and the base, leading to the formation of conjugate acid-base pairs.

Electron-Rich Atoms

Electron-rich atoms are typically those with lone pairs of electrons or negative charges, making them more likely to donate electrons in a reaction. In the context of bases, identifying the most electron-rich atom helps in understanding its reactivity and ability to accept protons during acid-base interactions.

Acidic Hydrogens

Acidic hydrogens are those that can be easily removed as protons in an acid-base reaction. They are usually attached to electronegative atoms, such as oxygen or nitrogen, which stabilize the resulting negative charge after deprotonation. Identifying the most acidic hydrogen is crucial for predicting the outcome of the reaction.

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Related Practice

Textbook Question

For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.

(a)

Textbook Question

In the following reactions,

(iv) provide an arrow-pushing mechanism of the proton transfer that will occur, and

(v) predict the product of the reactions. [You'll need to provide the lone pairs here.]

(c)

Textbook Question

In the following reactions,

(i) identify the acid and base,

(ii) identify the most electron-rich atom in the base,

(iii) identify the most acidic hydrogen in the acid,

(c)

Textbook Question

In the following reactions,

(iv) provide an arrow-pushing mechanism of the proton transfer that will occur, and

(v) predict the product of the reactions. [You'll need to provide the lone pairs here.]

(b)

Textbook Question

In the following reactions,

(iv) provide an arrow-pushing mechanism of the proton transfer that will occur, and

(v) predict the product of the reactions. [You'll need to provide the lone pairs here.]

(a)

Textbook Question

Provide an arrow-pushing mechanism for the following hypothetical acid half-reactions. [These are only intended to help you learn about arrow pushing in acid–base reactions.]

(b)

Textbook Question

Provide an arrow-pushing mechanism for the following hypothetical acid half-reactions. [These are only intended to help you learn about arrow pushing in acid–base reactions.]

(a)

Textbook Question

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

(c)

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