Textbook Question
What products are formed when each of the following reacts with HO−?
e. +CH3
f. FeBr3
3
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Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 2 - Acids and Bases: Central to Understanding Organic ChemistryProblem 57
Bruice 8th EditionCh. 2 - Acids and Bases: Central to Understanding Organic ChemistryProblem 57Chapter 3, Problem 57
Draw the products of the following reactions:
a. 
b. 
c. 
Verified step by step guidance1
Step 1: Analyze the reaction in part (a). The reactants are CH₃CH₂OCH₃ (an ether) and BH₃ (borane). Borane is an electron-deficient species due to the incomplete octet of boron, making it a Lewis acid. The lone pair of electrons on the oxygen atom in the ether can act as a Lewis base and donate electrons to boron.
Step 2: Predict the product for part (a). The oxygen atom in CH₃CH₂OCH₃ will form a coordinate covalent bond with boron in BH₃. This results in the formation of a Lewis acid-base adduct. The structure of the product will show the oxygen atom bonded to boron, with boron completing its octet.
Step 3: Analyze the reaction in part (b). The reactants are CH₃CH₂NH₂ (an amine) and AlF₃ (aluminum trifluoride). Aluminum in AlF₃ is electron-deficient due to its incomplete octet, making it a Lewis acid. The lone pair of electrons on the nitrogen atom in the amine can act as a Lewis base and donate electrons to aluminum.
Step 4: Predict the product for part (b). The nitrogen atom in CH₃CH₂NH₂ will form a coordinate covalent bond with aluminum in AlF₃. This results in the formation of a Lewis acid-base adduct. The structure of the product will show the nitrogen atom bonded to aluminum, with aluminum completing its octet.
Step 5: For both reactions, ensure that the products are drawn with proper chemical structures, showing the new bonds formed between the Lewis base (oxygen or nitrogen) and the Lewis acid (boron or aluminum). Include any lone pairs and formal charges if applicable.
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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 the reactions shown, BH3 acts as a Lewis acid, accepting electron pairs from the ether (CH3CH2OCH3), and AlF3 acts as a Lewis acid, interacting with the amine (CH3CH2NH2). Understanding these definitions is crucial for predicting the products of these reactions.
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02:49
The Lewis definition of acids and bases.
Nucleophilic Attack
Nucleophilic attack occurs when a nucleophile (an electron-rich species) donates an electron pair to an electrophile (an electron-deficient species). In the first reaction, the ether oxygen donates a pair of electrons to BH3, forming a new bond. Recognizing the nucleophile and electrophile in a reaction helps in determining the products formed.
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08:27Nucleophilic Addition
Reaction Mechanisms
Understanding reaction mechanisms involves knowing the step-by-step process by which reactants transform into products. This includes identifying intermediates and transition states. In the provided reactions, recognizing how the Lewis acids interact with the bases and the resulting bond formations is essential for accurately drawing the products.
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Related Practice
Textbook Question
b. How does the presence of an electronegative substituent such as Cl affect the acidity of a carboxylic acid?
c. How does the location of the substituent affect the acidity of the carboxylic acid?
Textbook Question
Explain the relative acidities.
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Textbook Question
Rank the following compounds from strongest to weakest acid:
CH3CH2OH; CH3CH2NH2; CH3CH2SH; CH3CH2CH3
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Textbook Question
For each of the following compounds, draw the form that predominates at pH = 3, pH = 6, pH = 10, and pH = 14:
a. CH3COOH (pKa = 4.8)
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Textbook Question
For each of the following compounds, draw the form that predominates at pH = 3, pH = 6, pH = 10, and pH = 14:
b. CH3CH2N+H3 (pKa = 11.0)
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