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)
1867
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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 51a
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) 
Verified step by step guidance1
Step 1: Identify the reactants in the given reaction. We have dimethylamine ((CH3)2NH) and hydrochloric acid (HCl).
Step 2: Determine the role of each reactant. Dimethylamine ((CH3)2NH) has a lone pair of electrons on the nitrogen atom, making it a Lewis base (nucleophile). Hydrochloric acid (HCl) can donate a proton (H+), making it a Lewis acid (electrophile).
Step 3: Use curved arrows to indicate the movement of electron pairs. The lone pair on the nitrogen atom of dimethylamine will attack the hydrogen atom of HCl, forming a bond between nitrogen and hydrogen.
Step 4: Draw the nonbonding electrons. After the nitrogen atom donates its lone pair to form a bond with hydrogen, the nitrogen will have a positive charge, resulting in (CH3)2(+NH2). The chloride ion (Cl-) will have a full octet and a negative charge.
Step 5: Review the electron movement and charges. The curved arrow should start from the lone pair on nitrogen and point towards the hydrogen atom in HCl, indicating the formation of a new N-H bond and the generation of Cl- as a byproduct.
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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, HCl acts as a Lewis acid because it accepts an electron pair from (CH3)2NH, which acts as a Lewis base by donating an electron pair.
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The Lewis definition of acids and bases.
Electrophiles and Nucleophiles
Electrophiles are electron-deficient species that seek electrons, whereas nucleophiles are electron-rich species that donate electrons. In the reaction, HCl is the electrophile as it seeks electrons, and (CH3)2NH is the nucleophile as it donates electrons to form a bond.
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Curved Arrow Notation
Curved arrows are used in organic chemistry to depict the movement of electron pairs during reactions. In this reaction, a curved arrow would show the electron pair from the nitrogen in (CH3)2NH moving towards the hydrogen in HCl, indicating the formation of a new bond and the generation of (CH3)2(+NH2) and Cl-.
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Related Practice
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.
(b)
1531
views
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.
942
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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+
1650
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1
rank
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.
750
views
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.
(c)
1568
views