Textbook Question
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
f.
1705
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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 4e
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
e. 
Verified step by step guidance1
Step 1: Analyze the structure of the given alkane. The provided structure is methylcyclopentane, which consists of a cyclopentane ring with a single methyl group attached to one of the carbons.
Step 2: Identify the types of hydrogen atoms present in the molecule. In methylcyclopentane, there are two types of hydrogens: (1) hydrogens on the cyclopentane ring and (2) hydrogens on the methyl group.
Step 3: Determine the number of unique carbon environments. The cyclopentane ring has five carbons, but due to symmetry, only two distinct environments exist: (a) the carbon attached to the methyl group and (b) the other carbons in the ring. The methyl group contributes a third unique environment.
Step 4: Consider monochlorination at each unique carbon environment. Chlorination can replace a hydrogen atom on any of these environments, leading to different alkyl chlorides. Disregard stereoisomers as stated in the problem.
Step 5: Count the number of unique alkyl chlorides formed. Each unique carbon environment leads to a distinct alkyl chloride. Therefore, the total number of alkyl chlorides corresponds to the number of unique carbon environments identified in Step 3.
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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 chemical reaction where one chlorine atom is introduced into an organic molecule, typically an alkane, through a free radical mechanism. This process involves the generation of free radicals, which react with the alkane to form alkyl chlorides. Understanding the conditions and mechanisms of monochlorination is essential for predicting the products formed during the reaction.
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Draw all of the monochlorination products and calculate percentage yields.
Alkyl Chlorides
Alkyl chlorides, or haloalkanes, are organic compounds derived from alkanes by replacing one or more hydrogen atoms with chlorine atoms. The structure and branching of the alkane influence the number of distinct alkyl chlorides that can be formed. Recognizing the different positions where chlorination can occur is crucial for determining the total number of products.
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Stereoisomers
Stereoisomers are compounds that have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of their atoms. In the context of monochlorination, disregarding stereoisomers means that only unique structural isomers are counted, simplifying the analysis of the products. This concept is important for accurately determining the number of distinct alkyl chlorides formed from the reaction.
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Related Practice
Textbook Question
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
g.
1120
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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?
859
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Textbook Question
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
a.
1172
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Textbook Question
How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.
h.
1134
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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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