Textbook Question
Predict the product of the following Lewis acid–Lewis base reactions.
(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 73d
Suggest an arrow-pushing mechanism for each of the following acid–base reactions.
(d) [an intramolecular reaction]
Verified step by step guidance1
Identify the functional groups involved in the reaction. The molecule contains a hydroxyl group (-OH) and a positively charged bromonium ion (+Br) attached to a cyclopropane ring.
Recognize that this is an intramolecular reaction, meaning the nucleophile (the hydroxyl group) and the electrophile (the bromonium ion) are part of the same molecule.
Determine the nucleophilic attack. The lone pair of electrons on the oxygen atom in the hydroxyl group will attack the electrophilic carbon in the bromonium ion, leading to the opening of the strained cyclopropane ring.
Show the arrow-pushing mechanism. Draw an arrow from the lone pair on the oxygen atom to the electrophilic carbon of the bromonium ion. Simultaneously, draw an arrow showing the breaking of the bond between the electrophilic carbon and the bromonium ion, resulting in the ring opening.
Account for the final structure. The attack forms a new bond between the oxygen and the carbon, creating a cyclic ether (a five-membered ring with oxygen). The bromonium ion is now attached to the other carbon atom in the ring.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acid-Base Reactions
Acid-base reactions involve the transfer of protons (H+) between reactants. In these reactions, acids donate protons while bases accept them. Understanding the strength of acids and bases, as well as their conjugate pairs, is crucial for predicting the direction of the reaction and the stability of the resulting species.
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02:49
The Lewis definition of acids and bases.
Arrow-Pushing Mechanism
Arrow-pushing mechanisms are a way to illustrate the movement of electrons during chemical reactions. Curved arrows represent the flow of electron pairs, indicating bond formation and breaking. This visual representation helps in understanding the stepwise progression of reactions, particularly in complex mechanisms like those involving intramolecular interactions.
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04:32General Mechanism
Intramolecular vs. Intermolecular Reactions
Intramolecular reactions occur within a single molecule, often leading to the formation of cyclic structures or rearrangements. In contrast, intermolecular reactions involve different molecules. Recognizing the distinction is essential for predicting the products and understanding the spatial orientation of reactants in acid-base reactions, especially in complex organic systems.
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Related Practice
Textbook Question
Predict the product of the following Lewis acid–Lewis base reactions.
(d) [an intramolecular reaction]
1448
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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.
1103
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Textbook Question
Consider the following drugs used to treat the indicated diseases. Would you expect the activity of these drugs to be impacted by a patient taking other medicines for acid reflux disease?
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Textbook Question
Suggest an arrow-pushing mechanism for each of the following acid–base reactions
(c)
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Textbook Question
BCl3 has an empty p orbital, so it is a strong Lewis acid. Would you expect an amide to react with BCl3 at nitrogen or oxygen?
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