Textbook Question
Provide an arrow-pushing mechanism for the following acid–base reactions.
(c)
1630
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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 17b
Provide an arrow-pushing mechanism for the following hypothetical base half-reactions.
(b) 
Verified step by step guidance1
Step 1: Identify the nucleophile and electrophile in the reaction. The oxygen atom with lone pairs in the ketone acts as the nucleophile, while the H⁺ (proton) acts as the electrophile.
Step 2: Draw the curved arrow to represent the movement of electrons. The lone pair of electrons on the oxygen atom will attack the H⁺, forming a bond between the oxygen and hydrogen.
Step 3: Update the structure of the ketone after the protonation. The oxygen atom now has a positive charge due to the addition of the proton, as it has gained a bond but lost one lone pair.
Step 4: Ensure the reaction is balanced. Verify that the number of atoms and charges are conserved in the reaction. The protonation of the ketone does not alter the carbon skeleton.
Step 5: Review the mechanism for clarity. Confirm that the arrow-pushing correctly represents the electron flow from the nucleophile (oxygen) to the electrophile (H⁺), resulting in the protonated ketone.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Arrow-Pushing Mechanism
Arrow-pushing is a notation used in organic chemistry to illustrate the movement of electrons during chemical reactions. It involves using arrows to show the direction of electron flow, indicating how bonds are formed or broken. This mechanism is crucial for visualizing reaction pathways, especially 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 donates a proton, while a base accepts it. Understanding the strength of acids and bases, as well as their conjugate pairs, is essential for predicting the outcome of these reactions and for applying the arrow-pushing mechanism correctly.
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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 becomes its conjugate base, and when a base accepts a proton, it becomes its conjugate acid. Recognizing these pairs is vital for understanding the equilibrium of acid-base reactions and the stability of the resulting species.
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2:56Base Pairing Concept 1
Related Practice
Textbook Question
Provide an arrow-pushing mechanism for the following acid–base reactions.
(d)
1672
views
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 base half-reactions.
(c)
1169
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Textbook Question
Based on the one species that is identified for you, label the remaining molecules as acid, base, conjugate acid, or conjugate base.
(c)
1105
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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