Textbook Question
What happens when a strong base such as KOH is dissolved in water?
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Ch.10 Acids and Bases
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187
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Table of contents
- Ch.1 Matter and Measurements27
- Ch.2 Atoms and the Periodic Table20
- Ch.3 Ionic Compounds8
- Ch.4 Molecular Compounds23
- Ch.5 Classification & Balancing of Chemical Reactions12
- Ch.6 Chemical Reactions: Mole and Mass Relationships28
- Ch.7 Chemical Reactions: Energy, Rate and Equilibrium64
- Ch.8 Gases, Liquids and Solids24
- Ch.9 Solutions52
- Ch.10 Acids and Bases25
- Ch.11 Nuclear Chemistry22
- Ch.12 Introduction to Organic Chemistry: Alkanes57
- Ch.13 Alkenes, Alkynes, and Aromatic Compounds47
- Ch.14 Some Compounds with Oxygen, Sulfur, or a Halogen50
- Ch.15 Aldehydes and Ketones45
- Ch.16 Amines42
- Ch.17 Carboxylic Acids and Their Derivatives57
- Ch.18 Amino Acids and Proteins82
- Ch.19 Enzymes and Vitamins63
- Ch.20 Carbohydrates44
- Ch.21 The Generation of Biochemical Energy65
- Ch.22 Carbohydrate Metabolism45
- Ch.23 Lipids42
- Ch.24 Lipid Metabolism33
- Ch.25 Protein and Amino Acid Metabolism24
- Ch.26 Nucleic Acids and Protein Synthesis45
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187Not the one you use?Change textbook
Chapter 10, Problem 34
Electrostatic potential maps of acetic acid (CH3CO2H) and ethyl alcohol (CH3CH2OH) are shown. Identify the most acidic hydrogen in each, and tell which of the two is likely to be the stronger acid.
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Verified step by step guidance1
Step 1: Examine the electrostatic potential maps provided for acetic acid (CH₃CO₂H) and ethyl alcohol (CH₃CH₂OH). The colors on the map indicate electron density, with red representing areas of high electron density (negative charge) and blue representing areas of low electron density (positive charge). Identify regions near hydrogen atoms to determine their acidity.
Step 2: In acetic acid (CH₃CO₂H), the hydrogen atom bonded to the oxygen in the carboxylic acid group (-CO₂H) is the most acidic. This is because the oxygen atoms in the carboxylic group are highly electronegative, pulling electron density away from the hydrogen, making it easier to lose as a proton (H⁺).
Step 3: In ethyl alcohol (CH₃CH₂OH), the hydrogen atom bonded to the oxygen in the hydroxyl group (-OH) is the most acidic. However, the alcohol group is less acidic compared to the carboxylic acid group because the single oxygen atom in the hydroxyl group does not stabilize the negative charge as effectively as the carboxylic group.
Step 4: Compare the acidity of acetic acid and ethyl alcohol. Acetic acid is likely to be the stronger acid because the carboxylic acid group can stabilize the negative charge on the conjugate base (CH₃CO₂⁻) through resonance, whereas the hydroxyl group in ethyl alcohol cannot.
Step 5: Conclude that the most acidic hydrogen in acetic acid is the one in the carboxylic acid group (-CO₂H), and the most acidic hydrogen in ethyl alcohol is the one in the hydroxyl group (-OH). Acetic acid is the stronger acid due to the resonance stabilization of its conjugate base.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acidity and Acid Strength
Acidity refers to the ability of a substance to donate protons (H⁺ ions) in a solution. The strength of an acid is determined by its tendency to dissociate in water, with stronger acids dissociating more completely. In organic compounds, factors such as electronegativity, resonance, and inductive effects influence acid strength, making some compounds more likely to release protons than others.
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Electrostatic Potential Maps
Electrostatic potential maps visually represent the distribution of electron density in a molecule, indicating regions of positive and negative charge. These maps help identify areas of high acidity by showing where protons are more likely to be released. In the context of acetic acid and ethyl alcohol, these maps can highlight the most acidic hydrogen atoms based on their surrounding electronic environment.
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Inductive Effect
The inductive effect refers to the electron-withdrawing or electron-donating influence of substituents on a molecule's acidity. Electronegative atoms or groups, such as halogens, can stabilize the negative charge of the conjugate base formed after deprotonation, enhancing acidity. In comparing acetic acid and ethyl alcohol, the presence of electron-withdrawing groups can significantly affect their relative acid strengths.
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Related Practice
Textbook Question
What happens when a weak acid such as CH3CO2H is dissolved in water?
Textbook Question
What happens when a strong acid such as HBr is dissolved in water?
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Textbook Question
Show how ethylamine (C2H5NH2) reacts with hydrochloric acid to form an ethylammonium salt.
Textbook Question
From this electrostatic potential map of the amino acid alanine, identify the most acidic hydrogens in the molecule:
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Textbook Question
Write a balanced equation for the proton transfer reaction between hydrofluoric acid (HF) and ammonia (NH3). Identify each conjugate acid-base pair, and rewrite the equilibrium arrows to indicate if the forward or reverse reaction is favored.
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