Textbook Question
Predict the product of the following Lewis acid–Lewis base reactions.
(c)
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 72d
Predict the product of the following Lewis acid–Lewis base reactions.
(d) [an intramolecular reaction]
Verified step by step guidance1
Step 1: Identify the Lewis acid and Lewis base in the reaction. In this case, the positively charged carbon atom (carbocation) is the Lewis acid, and the hydroxyl group (-OH) is the Lewis base.
Step 2: Recall that a Lewis acid is an electron pair acceptor, while a Lewis base is an electron pair donor. The hydroxyl group (-OH) has lone pairs of electrons on the oxygen atom, which can be donated to the carbocation.
Step 3: Predict the interaction between the Lewis acid and Lewis base. The lone pair of electrons from the oxygen atom in the hydroxyl group will form a bond with the carbocation, resulting in a new covalent bond.
Step 4: Consider the structure of the product. The oxygen atom from the hydroxyl group will now be directly bonded to the carbon atom that was previously the carbocation. This forms a new ether-like structure.
Step 5: Ensure the product is stable. Verify that all atoms in the product have complete octets and that the formal charges are minimized. The oxygen atom will likely retain a positive charge due to the bonding interaction.
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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 electron pair acceptors, while Lewis bases are electron pair donors. In a Lewis acid-base reaction, the base donates an electron pair to the acid, forming a coordinate covalent bond. Understanding this concept is crucial for predicting the products of reactions involving these species, as it determines how they interact and the resulting molecular structures.
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02:49
The Lewis definition of acids and bases.
Resonance Structures
Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. In the context of Lewis acid-base reactions, recognizing resonance can help predict the stability of intermediates and products. This is particularly important when dealing with charged species, as resonance can stabilize positive or negative charges, influencing the reaction pathway.
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03:04Drawing Resonance Structures
Nucleophilicity and Electrophilicity
Nucleophilicity refers to the ability of a species to donate an electron pair, while electrophilicity refers to the ability of a species to accept an electron pair. In the given reaction, the hydroxyl group (OH) acts as a nucleophile due to its lone pairs, while the positively charged site acts as an electrophile. Understanding these properties is essential for predicting the direction and outcome of the reaction.
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03:Nucleophile or Electrophile
Related Practice
Textbook Question
Using pKa values for the conjugate acids of the bases on each side of the reaction arrow, identify which side of the equilibrium would be favored in the following hypothetical reactions.
(c)
1
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Textbook Question
Suggest an arrow-pushing mechanism for each of the following acid–base reactions.
(d) [an intramolecular reaction]
Textbook Question
One of the more reactive species we will study in organic chemistry is the carbene (molecular formula of CH2). The carbene can react as both a Lewis acid and a Lewis base. Explain these properties.
Textbook Question
Using pKa values for the conjugate acids of the bases on each side of the reaction arrow, identify which side of the equilibrium would be favored in the following hypothetical reactions.
(a)
1
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Textbook Question
Suggest an arrow-pushing mechanism for each of the following acid–base reactions
(c)
2
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