Textbook Question
In the following reactions,
(i) identify the acid and base,
(ii) identify the most electron-rich atom in the base,
(iii) identify the most acidic hydrogen in the acid,
(c)
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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 20c(iv,v)
In the following reactions,
(iv) provide an arrow-pushing mechanism of the proton transfer that will occur, and
(v) predict the product of the reactions. [You'll need to provide the lone pairs here.]
(c) 
Verified step by step guidance1
Step 1: Identify the reactants and their roles in the proton transfer. Ethanolate (CH3CH2O⁻) is a strong base due to its negatively charged oxygen atom, which has lone pairs of electrons. Acetic acid (CH3COOH) is a weak acid, capable of donating a proton (H⁺) from its hydroxyl group (-OH).
Step 2: Recognize the site of interaction. The negatively charged oxygen atom in ethanolate will act as a nucleophile and attack the hydrogen atom of the hydroxyl group (-OH) in acetic acid. This is the proton transfer step.
Step 3: Draw the arrow-pushing mechanism. Use curved arrows to show the movement of electrons: (i) A lone pair of electrons on the oxygen atom of ethanolate attacks the hydrogen atom of acetic acid, forming a bond. (ii) Simultaneously, the bond between the hydrogen and oxygen in acetic acid breaks, and the electrons move to the oxygen atom of acetic acid, creating an acetate ion (CH3COO⁻).
Step 4: Predict the products of the reaction. The proton transfer results in the formation of ethanol (CH3CH2OH) and acetate ion (CH3COO⁻). Ethanol is formed as the ethanolate gains a proton, and acetate ion is formed as acetic acid loses a proton.
Step 5: Verify the stability of the products. Ethanol is neutral and stable, while acetate ion is resonance-stabilized due to the delocalization of electrons between the two oxygen atoms in the carboxylate group. This makes the reaction thermodynamically favorable.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Proton Transfer Mechanism
Proton transfer mechanisms involve the movement of a proton (H+) from one molecule to another, often facilitated by the presence of a base or acid. In this case, ethanolate acts as a base, accepting a proton from acetic acid. Understanding the arrow-pushing notation is crucial, as it visually represents the flow of electrons during the reaction, indicating how bonds are formed and broken.
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Acid-Base Reactions
Acid-base reactions are fundamental in organic chemistry, characterized by the transfer of protons between reactants. Acetic acid, a weak acid, donates a proton to the ethanolate ion, which is a strong base. Recognizing the strength of acids and bases helps predict the direction of the reaction and the stability of the resulting products.
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Lone Pairs and Bond Formation
Lone pairs are pairs of valence electrons that are not involved in bonding and can play a significant role in chemical reactions. In the context of the given reaction, the lone pair on the ethanolate ion is used to form a bond with the proton from acetic acid. Understanding how lone pairs participate in bond formation is essential for predicting the products of reactions and the overall mechanism.
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Related Practice
Textbook Question
In the following reactions,
(iv) provide an arrow-pushing mechanism of the proton transfer that will occur, and
(v) predict the product of the reactions. [You'll need to provide the lone pairs here.]
(b)
Textbook Question
Write the Keq expression for the following acid–base reactions. [You don't need to calculate Keq here.]
(c)
6
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Textbook Question
In the following reactions,
(i) identify the acid and base,
(ii) identify the most electron-rich atom in the base,
(iii) identify the most acidic hydrogen in the acid,
(iv) provide an arrow-pushing mechanism of the proton transfer that will occur, and
(v) predict the product of the reactions. [You'll need to provide the lone pairs here.]
(d) H2O + HCl ⇌
Textbook Question
In the following reactions,
(iv) provide an arrow-pushing mechanism of the proton transfer that will occur, and
(v) predict the product of the reactions. [You'll need to provide the lone pairs here.]
(a)
1
views
Textbook Question
In the following reactions,
(i) identify the acid and base,
(ii) identify the most electron-rich atom in the base,
(iii) identify the most acidic hydrogen in the acid,
(b)
3
views