Textbook Question
Predict the products formed when m-cresol (m-methylphenol) reacts with
(a) NaOH and then ethyl bromide
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Ch. 17 - Reactions of Aromatic Compounds
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 17, Problem 40
The bombardier beetle defends itself by spraying a hot quinone solution from its abdomen. This solution is formed by the enzyme-catalyzed oxidation of hydroquinone by hydrogen peroxide. Write a balanced equation for this oxidation.
Verified step by step guidance1
Identify the reactants and products in the reaction. The reactants are hydroquinone (C₆H₄(OH)₂) and hydrogen peroxide (H₂O₂), and the product is quinone (C₆H₄O₂). Water (H₂O) is also formed as a byproduct.
Write the unbalanced chemical equation for the reaction: C₆H₄(OH)₂ + H₂O₂ → C₆H₄O₂ + H₂O.
Balance the carbon atoms. Since the number of carbon atoms is already equal on both sides of the equation, no changes are needed here.
Balance the hydrogen atoms. Hydroquinone has 4 hydrogen atoms, and hydrogen peroxide has 2 hydrogen atoms, while quinone has 2 hydrogen atoms and water has 2 hydrogen atoms. The hydrogen atoms are already balanced in this case.
Balance the oxygen atoms. There are 4 oxygen atoms on the reactant side (2 from hydroquinone and 2 from hydrogen peroxide) and 4 oxygen atoms on the product side (2 from quinone and 2 from water). The oxygen atoms are balanced, so the equation is complete.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Enzyme-Catalyzed Reactions
Enzyme-catalyzed reactions involve biological catalysts that speed up chemical reactions without being consumed in the process. In the case of the bombardier beetle, enzymes facilitate the oxidation of hydroquinone, allowing the reaction to occur more efficiently at physiological temperatures. Understanding how enzymes work, including their specificity and the role of active sites, is crucial for writing balanced chemical equations.
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Oxidation-Reduction Reactions
Oxidation-reduction (redox) reactions involve the transfer of electrons between substances, leading to changes in oxidation states. In the oxidation of hydroquinone, hydroquinone loses electrons (is oxidized) while hydrogen peroxide acts as the oxidizing agent. Recognizing the roles of oxidizing and reducing agents is essential for balancing chemical equations and understanding the underlying chemistry.
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Balanced Chemical Equations
A balanced chemical equation represents a chemical reaction with equal numbers of each type of atom on both sides of the equation. Balancing involves adjusting coefficients to ensure mass conservation. For the oxidation of hydroquinone by hydrogen peroxide, it is important to identify the products formed and ensure that the equation adheres to the law of conservation of mass, which is fundamental in chemistry.
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Related Practice
Textbook Question
(c) Based on what you know about the relative stabilities of alkyl radicals and benzylic radicals, predict the product of addition of HBr to 1-phenylpropene in the presence of a free-radical initiator.
(d) Propose a mechanism for this reaction.
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Textbook Question
(a) Based on what you know about the relative stabilities of alkyl cations and benzylic cations, predict the product of addition of HBr to 1-phenylpropene.
(b) Propose a mechanism for this reaction.
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Textbook Question
Show how you would synthesize the following compounds, using the indicated starting materials.
(a) 3-phenylbutan-1-ol from styrene
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Textbook Question
Predict the products formed when m-cresol (m-methylphenol) reacts with
(c) bromine in CCl4 in the dark
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Textbook Question
Predict the products formed when m-cresol (m-methylphenol) reacts with
(b) acetyl chloride,
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