Domanda del libro di testo
Each of the three molecules shown here contains an OH group, but one molecule acts as a base, one as an acid, and the third is neither acid nor base. (c) Which one is neither acidic nor basic?
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Ch.16 - Acid-Base Equilibria
Brown14th EditionChemistry: The Central ScienceISBN: 9780134414232
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TOC.tableOfContents
- Ch.1 - Introduction: Matter, Energy, and Measurement177
- Ch.2 - Atoms, Molecules, and Ions231
- Ch.3 - Chemical Reactions and Reaction Stoichiometry216
- Ch.4 - Reactions in Aqueous Solution189
- Ch.5 - Thermochemistry175
- Ch.6 - Electronic Structure of Atoms168
- Ch.7 - Periodic Properties of the Elements150
- Ch.8 - Basic Concepts of Chemical Bonding177
- Ch.9 - Molecular Geometry and Bonding Theories200
- Ch.10 - Gases179
- Ch.11 - Liquids and Intermolecular Forces113
- Ch.12 - Solids and Modern Materials154
- Ch.13 - Properties of Solutions157
- Ch.14 - Chemical Kinetics199
- Ch.15 - Chemical Equilibrium128
- Ch.16 - Acid-Base Equilibria164
- Ch.17 - Additional Aspects of Aqueous Equilibria163
- Ch.18 - Chemistry of the Environment105
- Ch.19 - Chemical Thermodynamics164
- Ch.20 - Electrochemistry171
- Ch.21 - Nuclear Chemistry122
- Ch.22 - Chemistry of the Nonmetals82
- Ch.23 - Transition Metals and Coordination Chemistry79
- Ch.24 - The Chemistry of Life: Organic and Biological Chemistry16
Brown14th EditionChemistry: The Central ScienceISBN: 9780134414232Non è quello che usi tu?Cambia libro di testo
Capitolo 16, Problema 11a
Consider the molecular models shown here, where X represents a halogen atom. (a) If X is the same atom in both molecules, which molecule will be more acidic?
Guida verificata passo dopo passo1
Identify the functional groups in both molecules A and B. Molecule A has a hydroxyl group (-OH) attached to a carbon that is also bonded to a halogen (X). Molecule B has a carboxyl group (-COOH) attached to a carbon that is bonded to a halogen (X).
Recall that the acidity of a molecule is influenced by the stability of its conjugate base. The more stable the conjugate base, the more acidic the molecule.
Consider the inductive effect of the halogen (X). Halogens are electronegative and can withdraw electron density through the sigma bonds, stabilizing the conjugate base.
Compare the inductive effect in both molecules. In molecule B, the halogen (X) is closer to the carboxyl group, which can enhance the electron-withdrawing effect, making the conjugate base more stable.
Conclude that molecule B will be more acidic than molecule A because the inductive effect of the halogen (X) is stronger in molecule B, leading to a more stable conjugate base.
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Acidity and pKa
Acidity refers to the ability of a compound to donate a proton (H+) in solution. The strength of an acid is often measured by its pKa value; lower pKa values indicate stronger acids. In the context of the given molecules, the presence of electron-withdrawing groups can stabilize the negative charge on the conjugate base, thus increasing acidity.
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04:30
Acid-Base Indicators
Inductive Effect
The inductive effect describes the electron-withdrawing or electron-donating influence of substituents on a molecule. Halogens, being electronegative, exert a strong inductive effect, which can stabilize the conjugate base of an acid. In the comparison of the two molecules, the position and number of halogen atoms can significantly affect their acidity through this effect.
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02:31Photoelectric Effect
Resonance Stabilization
Resonance stabilization occurs when a molecule can be represented by multiple valid Lewis structures, allowing for the delocalization of electrons. This delocalization can stabilize the conjugate base formed after deprotonation, enhancing acidity. In the context of the two molecules, if one has a carbonyl group adjacent to the acidic site, it may provide additional resonance stabilization, making it more acidic.
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01:42Resonance Structures
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