Textbook Question
In each pair of atoms, which has the larger atomic radius? Which is more electronegative?
(c) O vs. S
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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 7b
Sodium amide (NaNH₂) dissociates to give a sodium cation (Na+) and amide ion (NH2–) a very strong base. In the following three equations, identify which definition of base is being exemplified.
(b) 
Verified step by step guidance1
Step 1: Analyze the chemical equation provided. Sodium amide (NaNH₂) reacts with water (H₂O) to produce hydroxide ion (OH⁻), sodium ion (Na⁺), and ammonia (NH₃).
Step 2: Recognize the role of NaNH₂ in the reaction. The amide ion (NH₂⁻) acts as a base by accepting a proton (H⁺) from water, forming NH₃.
Step 3: Identify the definition of a base being exemplified. According to the Brønsted-Lowry definition, a base is a substance that accepts a proton. Here, NH₂⁻ accepts a proton from H₂O, demonstrating the Brønsted-Lowry base behavior.
Step 4: Note the products formed. The hydroxide ion (OH⁻) is left behind after water donates a proton, and ammonia (NH₃) is formed as a result of NH₂⁻ accepting the proton.
Step 5: Conclude that the reaction exemplifies the Brønsted-Lowry definition of a base, as the amide ion (NH₂⁻) acts as a proton acceptor.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Brønsted-Lowry Base
A Brønsted-Lowry base is defined as a substance that can accept protons (H⁺ ions) in a chemical reaction. This concept emphasizes the role of bases in proton transfer processes, distinguishing them from other definitions that may focus solely on hydroxide ion production. In the context of sodium amide, the amide ion (NH₂⁻) acts as a Brønsted-Lowry base by accepting protons from acids.
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The Bronsted-Lowry definition of acids and bases.
Lewis Base
A Lewis base is defined as an electron pair donor in a chemical reaction. This definition broadens the concept of basicity beyond proton acceptance to include any species that can donate a pair of electrons to form a covalent bond. Sodium amide, through its amide ion, can act as a Lewis base by donating its lone pair of electrons to electrophiles.
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Strong Base
A strong base is a substance that completely dissociates in solution to produce hydroxide ions or other strong basic species. Sodium amide is classified as a strong base because it dissociates fully in water to yield sodium cations and amide ions, which are highly reactive and capable of deprotonating weak acids, thus demonstrating strong basic behavior.
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Related Practice
Textbook Question
What is the conjugate base of each of the following acids? [The most acidic proton is indicated.]
(a)
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Textbook Question
Sulfuric acid is a very strong acid. Show how the following equation can be used to explain that sulfuric acid is at once an Arrhenius, Brønsted–Lowry, and Lewis acid.
Textbook Question
Sodium amide (NaNH2) dissociates to give a sodium cation (Na+) and amide ion (NH2-) a very strong base. In the following three equations, identify which definition of base is being exemplified.
(c)
Textbook Question
Sodium amide (NaNH2) dissociates to give a sodium cation (Na+) and amide ion (NH2-) a very strong base. In the following three equations, identify which definition of base is being exemplified.
(a)
Textbook Question
In each pair of atoms, which has the larger atomic radius? Which is more electronegative?
(b) C vs. O
1
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