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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Problem 13

Textbook Question

When an atom loses a proton in an acid–base reaction, its formal charge is decreased by one. Thinking about the equation for calculating formal charge, explain this observation in your own words.

Verified step by step guidance

The formal charge of an atom is calculated using the formula:

F C = V - (N +_{B} /2)

, where

V

is the number of valence electrons in the neutral atom,

N

is the number of non-bonding electrons, and

B

is the number of bonding electrons.

When an atom loses a proton (H⁺) in an acid-base reaction, it typically loses a bond to hydrogen. This reduces the number of bonding electrons (

B

) by 2, as a single bond consists of two electrons.

In the formal charge equation, the term

B /2

decreases because the number of bonding electrons has been reduced. This makes the subtraction in the formula less negative, effectively decreasing the formal charge by 1.

Additionally, the atom does not gain or lose any non-bonding electrons (

N

) or valence electrons (

V

) in this process, so the change in formal charge is solely due to the loss of bonding electrons.

Thus, the decrease in formal charge by 1 reflects the loss of a proton and the associated bonding electrons in the acid-base reaction.

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Key Concepts

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

Formal Charge

Formal charge is a theoretical charge assigned to an atom in a molecule, calculated using the formula: Formal Charge = Valence Electrons - (Non-bonding Electrons + 1/2 Bonding Electrons). It helps in understanding the distribution of electrons in a molecule and predicting reactivity. A lower formal charge generally indicates a more stable structure.

Acid-Base Reactions

Acid-base reactions involve the transfer of protons (H+) between reactants. In these reactions, acids donate protons while bases accept them. The loss of a proton by an atom can lead to a change in its formal charge, as the number of protons in the nucleus directly influences the charge balance of the atom.

Proton Loss and Charge Change

When an atom loses a proton during an acid-base reaction, it effectively reduces its positive charge, as protons contribute to the overall charge of the atom. This decrease in positive charge results in a lower formal charge, which can stabilize the atom and influence the overall stability of the molecule involved in the reaction.

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Related Practice

Textbook Question

Identify the acid from which the following conjugate bases were formed. [The most basic atom is indicated.]

(c)

Textbook Question

Identify the base from which the following conjugate acids were formed. [The most acidic proton is indicated.]

(c)

Textbook Question

Using the convention that the acid and base are on the left side of the chemical equation, label the acid, base, conjugate acid, and conjugate base in the following reactions.

(a)

Textbook Question

Using the convention that the acid and base are on the left side of the chemical equation, label the acid, base, conjugate acid, and conjugate base in the following reactions.

(c)

Open Question

An unknown base (B⁻) has been identified as very weak. What does this tell you about the strength of its conjugate acid, HB? Is it stable or unstable? Is it reactive or unreactive?

Open Question

An unknown base (B⁻) has been identified as very weak. What does this tell you about the strength of its conjugate acid, HB? Is it stable or unstable? Is it reactive or unreactive?

Textbook Question

An unknown base (B⁻) has been identified as very weak. What does this tell you about the strength of its conjugate acid, HB? Is it stable or unstable? Is it reactive or unreactive?

Textbook Question

An unknown acid (HA) has been identified as very strong. What does this tell you about the stability of the conjugate base, A⁻? Is it strong or weak? Is it reactive or unreactive?

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