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 4b
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
b. 
Verified step by step guidance1
Step 1: Identify the structure of the given alkane. The provided structure is 2,3-dimethylpentane, which is a branched alkane.
Step 2: Determine all unique types of hydrogen atoms in the molecule. Hydrogens attached to different carbon environments will lead to different alkyl chlorides upon monochlorination. In this molecule, there are primary, secondary, and tertiary hydrogens.
Step 3: Count the number of unique carbon environments. The molecule has primary carbons (at the ends of the chain), secondary carbons (connected to two other carbons), and tertiary carbons (connected to three other carbons). Each unique carbon environment corresponds to a unique alkyl chloride upon monochlorination.
Step 4: Disregard stereoisomers as instructed. Focus only on the unique carbon environments, not the spatial arrangement of substituents.
Step 5: Sum up the number of unique alkyl chlorides formed. Each unique carbon environment will produce one type of alkyl chloride upon monochlorination.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Monochlorination
Monochlorination is a specific type of halogenation where one chlorine atom replaces a hydrogen atom in an alkane. This process typically occurs through a free radical mechanism, which involves the generation of chlorine radicals that abstract hydrogen atoms from the alkane, leading to the formation of alkyl chlorides. Understanding this process is crucial for predicting the products formed during the reaction.
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Draw all of the monochlorination products and calculate percentage yields.
Free Radical Mechanism
The free radical mechanism is a reaction pathway that involves the formation and reaction of free radicals, which are highly reactive species with unpaired electrons. In the context of monochlorination, the mechanism consists of three main steps: initiation, propagation, and termination. Each step plays a vital role in determining the number and types of alkyl chlorides produced from the starting alkane.
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Alkyl Chlorides
Alkyl chlorides are organic compounds derived from alkanes by substituting one or more hydrogen atoms with chlorine atoms. The structure and branching of the original alkane influence the variety of alkyl chlorides formed during monochlorination. Identifying the different alkyl chlorides is essential for understanding the outcomes of the chlorination reaction and for predicting their chemical behavior.
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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
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
g.
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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.
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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