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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1:16 minutes

Problem 17c

Textbook Question

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

Verified step by step guidance

Identify the base in the reaction. A base is a species that donates a pair of electrons to accept a proton (H⁺). Look for a lone pair of electrons or a negative charge on the base molecule.

Locate the acidic proton (H⁺) in the reaction. This is typically a hydrogen atom bonded to an electronegative atom, such as oxygen or nitrogen, which makes it more likely to be donated.

Draw a curved arrow starting from the lone pair of electrons on the base and pointing toward the acidic proton. This represents the base using its electrons to form a bond with the proton.

If the acidic proton is part of a bond (e.g., O-H or N-H), draw a second curved arrow starting from the bond between the proton and its atom, pointing toward the atom (e.g., oxygen or nitrogen). This shows the bond breaking and the electrons moving to the electronegative atom.

Verify the products of the reaction. The base should now have gained a proton (forming its conjugate acid), and the acidic molecule should have lost a proton (forming its conjugate base). Ensure the charges and electron counts are balanced in the final structures.

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Key Concepts

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

Arrow-Pushing Mechanism

The arrow-pushing mechanism is a visual representation used in organic chemistry to illustrate the movement of electrons during chemical reactions. Arrows indicate the direction of electron flow, showing how bonds are formed or broken. This technique is essential for understanding reaction mechanisms, particularly in acid-base reactions, where proton transfer occurs.

Acid-Base Reactions

Acid-base reactions involve the transfer of protons (H+) between reactants. An acid is defined as a proton donor, while a base is a proton acceptor. Understanding the strength of acids and bases, as well as their conjugate pairs, is crucial for predicting the outcome of these reactions and for applying the arrow-pushing mechanism effectively.

Conjugate Acid-Base Pairs

Conjugate acid-base pairs consist of two species that differ by the presence or absence of a proton. When an acid donates a proton, it forms its conjugate base, and when a base accepts a proton, it forms its conjugate acid. Recognizing these pairs is vital for understanding the equilibrium of acid-base reactions and for applying the arrow-pushing mechanism correctly.

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Related Practice

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)

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 acid–base reactions.

(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,

(a)

Textbook Question

For the following acid–base pairs,