Textbook Question
Label the reactants in these acid–base reactions as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions.
(d)
Ch. 2 - Acids and Bases; Functional Groups
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 2, Problem 51b
In each reaction, label the reactants as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions. Draw any nonbonding electrons to show how they participate in the reactions.
(b) 
Verified step by step guidance1
Identify the reactants: (CH3)2NH and CH3Cl. Determine which is the Lewis acid and which is the Lewis base. A Lewis acid is an electron pair acceptor, while a Lewis base is an electron pair donor.
Recognize that (CH3)2NH has a lone pair of electrons on the nitrogen atom, making it a Lewis base (nucleophile) because it can donate an electron pair.
Identify CH3Cl as the Lewis acid (electrophile) because the carbon atom is electron-deficient due to the electronegativity of the chlorine atom, making it capable of accepting an electron pair.
Use curved arrows to indicate the movement of electron pairs: Draw a curved arrow from the lone pair on the nitrogen atom of (CH3)2NH to the carbon atom of CH3Cl, showing the formation of a new bond.
Show the result of the electron movement: The nitrogen atom forms a bond with the carbon atom, resulting in (CH3)3(+NH) with a positive charge on nitrogen due to the addition of a proton, and Cl- as the leaving group with a negative charge.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Lewis Acids and Bases
Lewis acids are species that accept electron pairs, while Lewis bases donate electron pairs. In the given reaction, (CH3)2NH acts as a Lewis base because it donates an electron pair, and CH3Cl acts as a Lewis acid by accepting the electron pair, facilitating the formation of a new bond.
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The Lewis definition of acids and bases.
Curved Arrow Notation
Curved arrows are used in organic chemistry to depict the movement of electron pairs during chemical reactions. In this reaction, arrows should be drawn from the lone pair on the nitrogen atom in (CH3)2NH to the carbon atom in CH3Cl, indicating the nucleophilic attack and bond formation, and from the bond between carbon and chlorine to chlorine, showing bond cleavage.
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Nonbonding Electrons
Nonbonding electrons, or lone pairs, are valence electrons not involved in bonding. They play a crucial role in reactions as they can be donated to form new bonds. In this reaction, the lone pair on the nitrogen atom in (CH3)2NH is essential for the nucleophilic attack on CH3Cl, leading to the formation of (CH3)3(+NH) and Cl-.
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Related Practice
Textbook Question
Label the reactants in these acid–base reactions as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions.
i.
1
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Textbook Question
Each of these compounds can react as an electrophile. In each case, use curved arrows to show how the electrophile would react with the strong nucleophile sodium ethoxide, Na+ −OCH2CH3.
a.
b. NH4+
4
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Textbook Question
In each reaction, label the reactants as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions. Draw any nonbonding electrons to show how they participate in the reactions.
c.
1
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Textbook Question
In each reaction, label the reactants as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions. Draw any nonbonding electrons to show how they participate in the reactions.
(a)
1
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Textbook Question
Each of these compounds can react as an electrophile. In each case, use curved arrows to show how the electrophile would react with the strong nucleophile sodium ethoxide, Na+ −OCH2CH3.
(c) CH3CH2Br
(d) BH3
1
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