Textbook Question
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
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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 4h
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
h. 
Verified step by step guidance1
Step 1: Identify the structure of the given alkane. The image shows 2-methylbutane, which is a branched alkane with five carbon atoms.
Step 2: Determine the types of hydrogen atoms present in the molecule. In 2-methylbutane, there are primary, secondary, and tertiary hydrogens. Primary hydrogens are attached to primary carbons, secondary hydrogens are attached to secondary carbons, and tertiary hydrogens are attached to tertiary carbons.
Step 3: Analyze the possible sites for monochlorination. Monochlorination replaces one hydrogen atom with a chlorine atom. Each unique type of hydrogen atom leads to a different alkyl chloride product.
Step 4: Count the unique positions for hydrogen replacement. In 2-methylbutane, there are three unique positions: (1) the primary hydrogens on the terminal carbons, (2) the secondary hydrogens on the carbon adjacent to the methyl group, and (3) the tertiary hydrogen on the central carbon.
Step 5: Conclude the number of alkyl chlorides formed. Since stereoisomers are disregarded, each unique position leads to one distinct alkyl chloride. Therefore, the total number of alkyl chlorides is equal to the number of unique positions identified in Step 4.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Free Radical Halogenation
Free radical halogenation is a reaction mechanism where alkanes react with halogens (like chlorine) to form alkyl halides. This process involves the generation of free radicals through the homolytic cleavage of the halogen bond, followed by a series of propagation steps that lead to the substitution of hydrogen atoms with halogen atoms. Understanding this mechanism is crucial for predicting the products of monochlorination.
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Radical Chain Reaction Mechanism.
Monochlorination
Monochlorination refers to the substitution of a single hydrogen atom in an alkane with a chlorine atom. This process can yield multiple products depending on the number of unique hydrogen atoms available for substitution. The resulting alkyl chlorides can vary based on the structure of the alkane and the position of the chlorine substitution, making it essential to analyze the alkane's structure to determine the number of distinct products.
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04:37Draw all of the monochlorination products and calculate percentage yields.
Alkyl Chlorides
Alkyl chlorides are organic compounds formed when one or more hydrogen atoms in an alkane are replaced by chlorine atoms. They are classified based on the carbon atom to which the chlorine is attached, such as primary, secondary, or tertiary alkyl chlorides. The type of alkyl chloride produced during monochlorination is influenced by the stability of the resulting free radicals, which affects the likelihood of each substitution occurring.
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Related Practice
Textbook Question
If cyclopentane reacts with more than one equivalent of Cl2 at a high temperature, how many dichlorocyclopentanes would you expect to obtain as products?
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Textbook Question
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
g.
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Textbook Question
How many alkyl halides are obtained from monochlorination of the alkanes in Problem 4 if stereoisomers are included?
b.
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Textbook Question
How many alkyl halides are obtained from monochlorination of the alkanes in Problem 4 if stereoisomers are included?
a.
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Textbook Question
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
e.
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