Textbook Question
Write the steps for formation of tetrachloromethane (CCl4) from the reaction of methane with Cl2 + hv.
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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 4a
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
a. 
Verified step by step guidance1
Step 1: Identify the structure of the given alkane. The image shows a straight-chain alkane with five carbon atoms, which is pentane (C₅H₁₂).
Step 2: Understand monochlorination. Monochlorination involves replacing one hydrogen atom in the alkane with a chlorine atom, resulting in alkyl chlorides.
Step 3: Determine the types of hydrogen atoms in pentane. Pentane has three types of hydrogen atoms based on the carbon they are attached to: primary (on the terminal carbons), secondary (on the carbons adjacent to the terminal carbons), and tertiary (none in this case).
Step 4: Analyze the possible products. Chlorination at different types of hydrogen atoms will yield different alkyl chlorides. For pentane, chlorination at the primary hydrogens (on C1 and C5) and secondary hydrogens (on C2, C3, and C4) will result in distinct products.
Step 5: Count the unique alkyl chlorides. Since stereoisomers are disregarded, focus only on the unique connectivity of the chlorine atom to the carbon chain. Chlorination at C1 and C5 yields the same product, while chlorination at C2, C3, and C4 yields distinct products. Thus, there are three unique alkyl chlorides.
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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, leading to a series of chain reactions. Understanding this mechanism is crucial for predicting the products formed during the monochlorination of alkanes.
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Radical Chain Reaction Mechanism.
Monochlorination
Monochlorination refers to the substitution of one hydrogen atom in an alkane with a chlorine atom, resulting in the formation of an alkyl chloride. The number of distinct alkyl chlorides produced depends on the structure of the alkane and the positions available for substitution. In this context, it is important to consider the unique carbon environments in the alkane to determine the possible products.
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04:37Draw all of the monochlorination products and calculate percentage yields.
Alkyl Chlorides
Alkyl chlorides are organic compounds derived from alkanes by replacing one or more hydrogen atoms with chlorine atoms. They can vary in structure based on the carbon chain and branching of the original alkane. Identifying the different alkyl chlorides formed during monochlorination is essential for understanding the reactivity and properties of these compounds in organic chemistry.
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Related Practice
Textbook Question
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
f.
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Textbook Question
Write the initiation, propagation, and termination steps for the monochlorination of cyclohexane.
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Textbook Question
a. Which of the hydrogens in the structure in the margin is the easiest for a chlorine radical to remove?
b. How many secondary hydrogens does the structure have?
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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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Textbook Question
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
b.
1169
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