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 51a,b
Bruice 8th EditionCh. 2 - Acids and Bases: Central to Understanding Organic ChemistryProblem 51a,bChapter 3, Problem 51a,b
Draw the products of the following reactions. Use curved arrows to show where the pair of electrons starts and where it ends up.
a. 
b. 
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Verified step by step guidance1
Step 1: Analyze the reaction (i) ZnBr₂ + H₂O. ZnBr₂ is a Lewis acid because Zn has an incomplete octet, and H₂O is a Lewis base due to the lone pairs on oxygen. The reaction involves the donation of a lone pair of electrons from H₂O to ZnBr₂.
Step 2: Use curved arrows to show the movement of electrons in reaction (i). Draw an arrow starting from one of the lone pairs on the oxygen atom of H₂O and pointing toward the Zn atom in ZnBr₂, indicating the formation of a coordinate covalent bond.
Step 3: Predict the product of reaction (i). The product will be a complex where ZnBr₂ is bonded to H₂O through the oxygen atom. Represent this as [ZnBr₂(H₂O)] with the oxygen atom donating its lone pair to Zn.
Step 4: Analyze the reaction (ii) FeCl₃ + Cl⁻. FeCl₃ is a Lewis acid because Fe has an incomplete octet, and Cl⁻ is a Lewis base due to its negative charge and lone pairs. The reaction involves the donation of a lone pair of electrons from Cl⁻ to Fe in FeCl₃.
Step 5: Use curved arrows to show the movement of electrons in reaction (ii). Draw an arrow starting from one of the lone pairs on Cl⁻ and pointing toward the Fe atom in FeCl₃, indicating the formation of a coordinate covalent bond. The product will be a complex represented as [FeCl₄]⁻, where Fe is bonded to four Cl atoms.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Curved Arrows in Organic Chemistry
Curved arrows are used to represent the movement of electron pairs during chemical reactions. The tail of the arrow indicates the starting point of the electrons, while the head shows where they are moving. This notation helps visualize mechanisms, including nucleophilic attacks and bond formations or breakages, which are crucial for understanding reaction pathways.
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What is an organic molecule?
Lewis Acids and Bases
In organic chemistry, Lewis acids are electron pair acceptors, while Lewis bases are electron pair donors. In the reactions shown, ZnBr2 acts as a Lewis acid by accepting electron pairs from water, while FeCl3 accepts electrons from the chloride ion. Understanding these roles is essential for predicting the products of reactions and the stability of intermediates.
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02:49The Lewis definition of acids and bases.
Electrophiles and Nucleophiles
Electrophiles are species that seek electrons and are typically positively charged or neutral with an electron-deficient atom, while nucleophiles are electron-rich species that donate electron pairs. In the given reactions, ZnBr2 and FeCl3 serve as electrophiles, reacting with nucleophiles like water and chloride ions, respectively. Recognizing these roles is vital for analyzing reaction mechanisms and predicting outcomes.
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Related Practice
Textbook Question
Given the data in Problem 47:
b. What pH would you make the water layer to cause the carboxylic acid to dissolve in the water layer and the amine to dissolve in the ether layer?
1
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Textbook Question
Given the data in Problem 47:
a. What pH would you make the water layer to cause the carboxylic acid to dissolve in the water layer and the amine to dissolve in the ether layer?
1
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Textbook Question
What products are formed when each of the following reacts with HO−?
a. CH3OH
b. +NH4
3
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Textbook Question
Write the equation that shows how a buffer made by dissolving CH3COOH and CH3COO−Na+ in water prevents the pH of a solution from changing appreciably when
a. a small amount of H+ is added to the solution.
b. a small amount of HO− is added to the solution.
1
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Textbook Question
What products are formed when each of the following reacts with HO−?
c. CH3N+H3
d. BF3