Textbook Question
Given the following Keq values, how much stronger of a base is acetate (CH3CO2-) than chloride (Cl⁻)?
1055
views
Ch. 4 - Acids and Bases: Electron Flow
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
Not the one you use?Change textbookSelect a different textbook
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 28
Given the following Keq values, how much stronger of an acid is methanol (CH3OH) than acetylene (HC≡CH)?
Verified step by step guidance1
Identify the equilibrium constant (K_eq) values for methanol (CH₃OH) and acetylene (HC≡CH). These values are typically related to the acid dissociation constants (K_a) of the acids.
Recall that the strength of an acid is directly proportional to its K_a value. A higher K_a indicates a stronger acid.
To compare the acid strengths, calculate the ratio of the K_a values of methanol to acetylene. This can be expressed as:
Take the logarithm (base 10) of the ratio to express the difference in acid strength in terms of pKa values. Recall that .
Interpret the result: A difference of 1 in pKa corresponds to a 10-fold difference in acid strength. Use this relationship to determine how much stronger methanol is as an acid compared to acetylene.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
1mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acid-Base Strength
Acid-base strength is determined by the ability of an acid to donate protons (H⁺) in a solution. Stronger acids have a greater tendency to dissociate and release protons, leading to higher concentrations of H⁺ ions. The strength of an acid can be quantitatively expressed using the acid dissociation constant (K_a), where a larger K_a indicates a stronger acid.
Recommended video:
2:50
Acid-Base Catalysis Concept 3
Equilibrium Constant (K_eq)
The equilibrium constant (K_eq) is a numerical value that expresses the ratio of the concentrations of products to reactants at equilibrium for a given reaction. In acid-base reactions, K_eq can be used to compare the strengths of different acids. A higher K_eq value for an acid indicates that it is more likely to donate protons compared to another acid, thus being stronger.
Recommended video:
Guided course
02:19The relationship between equilibrium constant and pKa.
Comparative Acid Strength
To compare the strength of two acids, one can use the relationship between their K_a values or K_eq values. The difference in their K_eq values can be used to calculate how many times stronger one acid is compared to another. This comparison is essential in organic chemistry to predict the behavior of acids in various chemical reactions and their reactivity.
Recommended video:
Guided course
02:41Comparing hydrocarbon acidity
Related Practice
Textbook Question
Design an acid–base extraction scheme to separate a mixture of the basic amine N,N-dimethylaniline and naphthalene.
1353
views
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?
1100
views
Textbook Question
Given that the indicated pKa values correspond to the acid dissociation reactions shown, calculate the ratio of acid to conjugate base for the reactions shown.
(a)
925
views
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?
844
views
Textbook Question
Given that the indicated pKa values correspond to the acid dissociation reactions shown, calculate the ratio of acid to conjugate base for the reactions shown.
(b)
1261
views