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)
Ch. 4 - Acids and Bases: Electron Flow
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 3, Problem 13
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.
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The formal charge of an atom is calculated using the formula: , where is the number of valence electrons in the neutral atom, is the number of non-bonding electrons, and 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 () by 2, as a single bond consists of two electrons.
In the formal charge equation, the term 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 () or valence electrons () 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.
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Calculating formal and net charge.
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.
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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 acid from which the following conjugate bases were formed. [The most basic atom is indicated.]
(d)
1
views
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.
(b)
1
views
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.
(c)