Textbook Question
Propose a mechanism for the following reaction:
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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 46f
Draw the products of the following reactions, including all stereoisomers:
f. 
Verified step by step guidance1
Step 1: Recognize the reaction type. The reaction involves NBS (N-Bromosuccinimide) in the presence of heat (Δ) and peroxide. This is a radical bromination reaction that selectively brominates allylic positions due to the stability of the allylic radical.
Step 2: Identify the allylic position in the given molecule. The allylic position is the carbon atom adjacent to the double bond. In this case, the allylic position is the carbon atom directly connected to the double bond in the side chain.
Step 3: Generate the allylic radical intermediate. The peroxide initiates the formation of a bromine radical, which abstracts a hydrogen atom from the allylic position, forming a stable allylic radical.
Step 4: Add the bromine atom to the allylic radical. The bromine radical reacts with the allylic radical to form the brominated product at the allylic position.
Step 5: Consider stereoisomers. Since the allylic position is not a stereocenter in this molecule, no stereoisomers are formed. The product will be a single brominated compound at the allylic position.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Allylic Bromination
Allylic bromination is a reaction where bromine is added to the allylic position of an alkene, typically using N-bromosuccinimide (NBS) in the presence of a peroxide. This reaction proceeds via a radical mechanism, where the allylic hydrogen is abstracted, forming a resonance-stabilized radical that can then react with bromine to yield brominated products.
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Mechanism of Allylic Bromination.
Radical Mechanism
A radical mechanism involves the formation and reaction of free radicals, which are highly reactive species with unpaired electrons. In the context of allylic bromination, the reaction starts with the generation of a radical intermediate through the homolytic cleavage of a bond, allowing for subsequent reactions that lead to the formation of products, including stereoisomers.
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Stereoisomerism
Stereoisomerism refers to the existence of compounds with the same molecular formula and connectivity but different spatial arrangements of atoms. In the case of allylic bromination, the formation of stereoisomers occurs due to the different orientations of substituents around the double bond, leading to distinct products that must be accounted for when drawing the final reaction products.
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Related Practice
Textbook Question
Draw the products of the following reactions, including all stereoisomers:
c.
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Textbook Question
A possible alternative mechanism to that shown in Problem 47 for the monochlorination of methane involves the following propagation steps:
How do you know that the reaction does not take place by this mechanism?
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Textbook Question
Calculate the ∆H° value for the following reaction:
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Textbook Question
Draw the products of the following reactions, including all stereoisomers:
e.
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Textbook Question
Draw the products of the following reactions, including all stereoisomers:
d.
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