Textbook Question
What are the product(s) of each of the following reactions? Disregard stereoisomers.
c.
1
views
Ch. 12 - Radicals
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
Not the one you use?Change textbookSelect a different textbook
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 26e
What are the product(s) of each of the following reactions? Disregard stereoisomers.
e. 
Verified step by step guidance1
Step 1: Identify the type of reaction. The reaction involves cyclohexane (C6H12) and chlorine (Cl2) in the presence of dichloromethane (CH2Cl2) as the solvent. This is a free radical halogenation reaction, typically initiated by light or heat.
Step 2: Understand the mechanism. Free radical halogenation proceeds via three steps: initiation, propagation, and termination. In the initiation step, chlorine molecules are split into two chlorine radicals (Cl•) by light or heat.
Step 3: Analyze the propagation step. A chlorine radical abstracts a hydrogen atom from cyclohexane, forming a cyclohexyl radical and HCl. The cyclohexyl radical then reacts with another chlorine molecule to form chlorocyclohexane and regenerate a chlorine radical.
Step 4: Consider the product. Since stereoisomers are disregarded, the major product will be chlorocyclohexane (C6H11Cl), where one hydrogen atom on the cyclohexane ring is replaced by a chlorine atom.
Step 5: Note the regioselectivity. In this case, all hydrogens in cyclohexane are equivalent, so the chlorine can attach to any carbon atom in the ring, resulting in a single product without regioselectivity concerns.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
2mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophilic Halogenation
Electrophilic halogenation is a reaction where an alkene or alkane reacts with a halogen (like Cl2) to form a haloalkane. In this process, the halogen acts as an electrophile, attacking the electron-rich double bond or the C-H bonds in alkanes, leading to the substitution of hydrogen atoms with halogen atoms.
Recommended video:
Guided course
03:45
Halogenation Mechanism
Mechanism of Free Radical Halogenation
The mechanism of free radical halogenation involves three main steps: initiation, propagation, and termination. In the initiation step, Cl2 is dissociated into two chlorine radicals. During propagation, these radicals react with cyclohexane to form dichlorocyclohexane and additional radicals, which can continue the reaction. Termination occurs when two radicals combine to form a stable product.
Recommended video:
Guided course
12:11Radical Chain Reaction Mechanism.
Dichlorocyclohexane Isomers
Dichlorocyclohexane can exist in multiple isomeric forms due to the different positions where chlorine atoms can be substituted on the cyclohexane ring. However, the question specifies to disregard stereoisomers, focusing only on the structural isomers that result from the substitution of hydrogen atoms with chlorine, leading to products like 1,2-dichlorocyclohexane and 1,4-dichlorocyclohexane.
Recommended video:
Guided course
01:10What is a constitutional isomer?
Related Practice
Textbook Question
How many atoms share the unpaired electron in semiquinone?
10
views
Textbook Question
What are the product(s) of each of the following reactions? Disregard stereoisomers.
f.
2
views
Textbook Question
Explain why iodine (I2) does not react with ethane, even though I2 is more easily cleaved homolytically than the other halogens.
1
views
Textbook Question
What are the product(s) of each of the following reactions? Disregard stereoisomers.
d.
2
views
Textbook Question
What alkane, with molecular formula C5H12, forms only one monochlorinated product when it is heated with Cl2?
7
views