Textbook Question
Provide an arrow-pushing mechanism for the following hypothetical base half-reactions.
(b)
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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 17c
Provide an arrow-pushing mechanism for the following hypothetical base half-reactions.
(c) 
Verified step by step guidance1
Identify the base in the reaction. A base is a species that donates a pair of electrons to accept a proton (H⁺). Look for a lone pair of electrons or a negative charge on the base molecule.
Locate the acidic proton (H⁺) in the reaction. This is typically a hydrogen atom bonded to an electronegative atom, such as oxygen or nitrogen, which makes it more likely to be donated.
Draw a curved arrow starting from the lone pair of electrons on the base and pointing toward the acidic proton. This represents the base using its electrons to form a bond with the proton.
If the acidic proton is part of a bond (e.g., O-H or N-H), draw a second curved arrow starting from the bond between the proton and its atom, pointing toward the atom (e.g., oxygen or nitrogen). This shows the bond breaking and the electrons moving to the electronegative atom.
Verify the products of the reaction. The base should now have gained a proton (forming its conjugate acid), and the acidic molecule should have lost a proton (forming its conjugate base). Ensure the charges and electron counts are balanced in the final structures.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Arrow-Pushing Mechanism
The arrow-pushing mechanism is a visual representation used in organic chemistry to illustrate the movement of electrons during chemical reactions. Arrows indicate the direction of electron flow, showing how bonds are formed or broken. This technique is essential for understanding reaction mechanisms, particularly in acid-base reactions, where proton transfer occurs.
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04:32
General Mechanism
Acid-Base Reactions
Acid-base reactions involve the transfer of protons (H+) between reactants. An acid is defined as a proton donor, while a base is a proton acceptor. Understanding the strength of acids and bases, as well as their conjugate pairs, is crucial for predicting the outcome of these reactions and for applying the arrow-pushing mechanism effectively.
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02:49The Lewis definition of acids and bases.
Conjugate Acid-Base Pairs
Conjugate acid-base pairs consist of two species that differ by the presence or absence of a proton. When an acid donates a proton, it forms its conjugate base, and when a base accepts a proton, it forms its conjugate acid. Recognizing these pairs is vital for understanding the equilibrium of acid-base reactions and for applying the arrow-pushing mechanism correctly.
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2:56Base Pairing Concept 1
Related Practice
Textbook Question
Provide an arrow-pushing mechanism for the following acid–base reactions.
(c)
1630
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Textbook Question
Acid–base reactions are reversible. Show a mechanism for the reverse of the reactions in Assessment 4.18.
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Textbook Question
Provide an arrow-pushing mechanism for the following acid–base reactions.
(d)
1672
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Textbook Question
Provide an arrow-pushing mechanism for the following hypothetical acid half-reactions. [These are only intended to help you learn about arrow pushing in acid–base reactions.]
(b)
1589
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Textbook Question
Provide an arrow-pushing mechanism for the following hypothetical acid half-reactions. [These are only intended to help you learn about arrow pushing in acid–base reactions.]
(a)
1018
views