Textbook Question
What are the product(s) of each of the following reactions? Disregard stereoisomers.
c.
1
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Ch. 12 - Radicals
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
Chapter 13, Problem 24
How many atoms share the unpaired electron in semiquinone?
Verified step by step guidance1
Step 1: Recognize the structure of semiquinone. Semiquinone is a radical species derived from quinones, where one of the oxygen atoms has an unpaired electron. The structure provided shows a benzene ring with an oxygen atom attached, carrying an unpaired electron.
Step 2: Understand the delocalization of the unpaired electron. In semiquinone, the unpaired electron is not localized on the oxygen atom alone but is delocalized over the conjugated π-system of the benzene ring and the oxygen atom.
Step 3: Analyze the conjugated system. The benzene ring has alternating double bonds, which form a conjugated π-system. The oxygen atom is connected to the ring, allowing the unpaired electron to interact with the π-system.
Step 4: Determine the atoms involved in delocalization. The delocalization occurs over the oxygen atom and the carbon atoms of the benzene ring that are part of the conjugated π-system. This includes the oxygen atom and six carbon atoms of the benzene ring.
Step 5: Conclude the number of atoms sharing the unpaired electron. The unpaired electron is shared among seven atoms: the oxygen atom and the six carbon atoms of the benzene ring.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Radicals
Radicals are species that contain unpaired electrons, making them highly reactive. In organic chemistry, they often participate in various reactions, including addition and substitution. Understanding the nature of radicals is crucial for analyzing their stability and reactivity, particularly in compounds like semiquinone, which features an unpaired electron.
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Semiquinone Structure
Semiquinones are a class of organic compounds derived from quinones, characterized by having one unpaired electron. This unpaired electron can be localized on one of the carbon atoms in the ring structure, influencing the compound's chemical behavior. Recognizing the specific atom that holds the unpaired electron is essential for understanding the properties and reactivity of semiquinones.
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Electron Delocalization
Electron delocalization refers to the distribution of electrons across multiple atoms in a molecule, which can stabilize radicals and influence their reactivity. In semiquinones, the unpaired electron may be delocalized over the aromatic ring, affecting the overall stability and reactivity of the compound. This concept is vital for predicting how semiquinones will interact in chemical reactions.
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Related Practice
Textbook Question
Design a multistep synthesis to show how the following compounds can be prepared from the given starting material:
d.
Textbook Question
What are the product(s) of each of the following reactions? Disregard stereoisomers.
e.
5
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Textbook Question
What are the product(s) of each of the following reactions? Disregard stereoisomers.
d.
2
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Textbook Question
Design a multistep synthesis to show how the following compounds can be prepared from the given starting material:
a.
8
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Textbook Question
For each reaction, show which stereoisomers are obtained
1. NBS/∆/peroxide
2. Br2/CH2Cl2
4
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