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.
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)
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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)
Textbook Question
In each pair of atoms, which has the larger atomic radius? Which is more electronegative?
(b) C vs. O
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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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