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How many atoms share the unpaired electron in semiquinone?
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Ch. 12 - Radicals
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- 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
Capitolo 12, Problema 26c
What are the product(s) of each of the following reactions? Disregard stereoisomers.
c. 
Guida verificata passo dopo passo1
Step 1: Recognize the type of reaction. The presence of Br₂ and light (hν) indicates a free radical halogenation reaction, specifically bromination.
Step 2: Identify the substrate. The given molecule is 2-methylbutane, a branched alkane.
Step 3: Determine the most reactive hydrogen for bromination. Bromine prefers to react with the hydrogen attached to the most substituted carbon due to the stability of the resulting radical. In this case, the tertiary carbon (the central carbon in the molecule) is the most substituted.
Step 4: Predict the product. Bromine will replace the hydrogen on the tertiary carbon, forming 2-bromo-2-methylbutane as the major product.
Step 5: Note that minor products may form due to bromination at other positions, but the major product is determined by the stability of the intermediate radical.
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Free Radical Halogenation
Free radical halogenation is a reaction where alkenes react with halogens (like Br2) in the presence of light (hν) to form alkyl halides. The process involves the generation of free radicals, which are highly reactive species with unpaired electrons. The reaction typically proceeds through initiation, propagation, and termination steps, leading to the substitution of hydrogen atoms in the alkene with halogen atoms.
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Radical Chain Reaction Mechanism.
Mechanism of Radical Reactions
The mechanism of radical reactions involves several key steps: initiation (where radicals are formed), propagation (where radicals react with stable molecules to form new radicals), and termination (where radicals combine to form stable products). In the case of bromination, the bromine molecule dissociates into two bromine radicals, which then react with the alkene to form bromoalkanes. Understanding this mechanism is crucial for predicting the products of the reaction.
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12:11Radical Chain Reaction Mechanism.
Regioselectivity in Electrophilic Addition
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple products are possible. In the context of alkene bromination, the regioselectivity is influenced by the stability of the radical intermediates formed during the reaction. The more stable radical will lead to the major product, which is often determined by the degree of substitution of the carbon atom where the bromine adds.
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