Textbook Question
Methyllithium (CH3Li) is often used as a base in organic reactions.
b. What is the conjugate acid of CH3Li? Would you expect CH3Li to be a strong base or a weak base?
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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 50c
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) 
Verified step by step guidance1
Identify the reactants: In the given reaction, the reactants are formaldehyde (HCOH) and ammonia (NH3).
Determine the Lewis acid and Lewis base: A Lewis acid is an electron pair acceptor, while a Lewis base is an electron pair donor. In this reaction, formaldehyde (HCOH) acts as the Lewis acid because the carbonyl carbon can accept an electron pair. Ammonia (NH3) acts as the Lewis base because it has a lone pair of electrons on the nitrogen atom that can be donated.
Draw the curved arrow notation: Use a curved arrow to show the movement of the electron pair from the nitrogen atom of NH3 to the carbonyl carbon of HCOH. This represents the nucleophilic attack of the Lewis base on the Lewis acid.
Analyze the product formation: As a result of the electron pair donation, the carbonyl carbon forms a new bond with the nitrogen atom, resulting in the formation of a tetrahedral intermediate. The oxygen atom in the carbonyl group gains a negative charge, and the nitrogen atom gains a positive charge.
Label the products: The products of the reaction are the ammonium ion (NH4+) and the alkoxide ion (CH3C(OH)CH3-). The ammonium ion is formed by the protonation of NH3, and the alkoxide ion is formed by the deprotonation of the hydroxyl group in the intermediate.
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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 can accept an electron pair, while Lewis bases are species that can donate an electron pair. In the given reaction, the carbonyl compound acts as a Lewis acid due to the electrophilic carbon, and ammonia acts as a Lewis base because it has a lone pair of electrons available for donation.
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Guided course
02:49
The Lewis definition of acids and bases.
Curved Arrows in Mechanisms
Curved arrows are used in organic chemistry to illustrate the movement of electron pairs during chemical reactions. The tail of the arrow indicates the source of the electrons, while the head points to where the electrons are going. This notation helps visualize the flow of electrons, which is crucial for understanding reaction mechanisms.
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04:32General Mechanism
Acid-Base Reactions
Acid-base reactions involve the transfer of protons (H+) or electron pairs between reactants. In this case, the reaction between the carbonyl compound and ammonia is an acid-base reaction where the Lewis base (ammonia) donates an electron pair to the Lewis acid (carbonyl), forming a new bond and resulting in a charged intermediate.
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02:49The Lewis definition of acids and bases.
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.
(d)
1867
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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
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.
(b)
1446
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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)
1597
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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.
(a)
1286
views