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 7a
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) 
Verified step by step guidance1
Step 1: Recall the three main definitions of a base in chemistry: (1) Arrhenius base - a substance that increases the concentration of OH⁻ ions in aqueous solution, (2) Brønsted-Lowry base - a substance that accepts a proton (H⁺), and (3) Lewis base - a substance that donates a pair of electrons.
Step 2: Analyze the dissociation of sodium amide (NaNH₂). When NaNH₂ dissociates, it forms Na⁺ and NH₂⁻. The NH₂⁻ ion is a strong base. Determine which definition of a base applies to this behavior.
Step 3: For each equation provided, examine the role of NH₂⁻. If NH₂⁻ is accepting a proton (H⁺), it is acting as a Brønsted-Lowry base. If NH₂⁻ is donating a pair of electrons to form a bond, it is acting as a Lewis base.
Step 4: For equation (a), identify whether NH₂⁻ is increasing the concentration of OH⁻ ions in solution (Arrhenius base), accepting a proton (Brønsted-Lowry base), or donating an electron pair (Lewis base).
Step 5: Match the behavior of NH₂⁻ in equation (a) to the appropriate base definition and repeat this process for the other equations to identify the base definition being exemplified in each case.
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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. In the context of sodium amide, the amide ion (NH₂⁻) acts as a Brønsted-Lowry base by accepting protons from acids, thereby facilitating various acid-base reactions.
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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. Sodium amide's amide ion can donate a pair of electrons to form a bond with a Lewis acid, demonstrating its behavior as a Lewis base. This concept broadens the understanding of basicity beyond proton transfer.
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Strong Base
A strong base is a substance that completely dissociates in solution to produce hydroxide ions (OH⁻) or other strong basic ions. Sodium amide is classified as a strong base because it dissociates fully in solution, resulting in the formation of the highly reactive amide ion, which can readily deprotonate weak acids.
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Related Practice
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.
780
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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.
(b)
1047
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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)
1327
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Textbook Question
In each pair of atoms, which has the larger atomic radius? Which is more electronegative?
(b) C vs. O
1014
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Textbook Question
Draw the molecular orbital picture of the following molecules and ions. In each, how many electrons are in the p orbital on the central atom? (c) AlCl3
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