Textbook Question
The radical fluorination of 2-methyl propane resulted in a 14:86 ratio of products.
(a) On the basis of this ratio, calculate the relative reactivity of 1° and 3° C―H bonds in the radical fluorination.
1
views
Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
Not the one you use?Change textbookSelect a different textbook
Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
All textbooks
Mullins 1st EditionCh. 5 - Chemical Reaction Analysis: Thermodynamics and KineticsProblem 46c
Mullins 1st EditionCh. 5 - Chemical Reaction Analysis: Thermodynamics and KineticsProblem 46cChapter 4, Problem 46c
Predict the major monohalogenation product(s) of the following reactions. Indicate whether you think the reaction will be selective and justify your position.
(c) 
Verified step by step guidance1
Step 1: Recognize the reaction type. This is a free radical halogenation reaction involving chlorine (Cl₂) and heat. Free radical halogenation typically proceeds via a radical mechanism and is less selective compared to bromination.
Step 2: Analyze the structure of the starting compound. The molecule is 2,2,3-trimethylbutane, which has primary, secondary, and tertiary hydrogens available for substitution.
Step 3: Determine the relative reactivity of the hydrogens. In free radical halogenation, tertiary hydrogens are the most reactive, followed by secondary hydrogens, and then primary hydrogens. This is due to the stability of the resulting radical intermediates.
Step 4: Identify the possible sites for monohalogenation. The tertiary hydrogen on the central carbon (C3) is the most likely site for substitution due to the formation of a highly stable tertiary radical. Secondary hydrogens on adjacent carbons (C2) may also be substituted, but less likely.
Step 5: Evaluate the selectivity of the reaction. Chlorination is not highly selective, so multiple products may form. However, the major product will likely result from substitution at the tertiary position due to the stability of the tertiary radical intermediate.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Was this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Monohalogenation
Monohalogenation refers to the substitution reaction where one halogen atom replaces a hydrogen atom in an organic compound. This process typically occurs in alkanes and can be initiated by heat or light, leading to the formation of haloalkanes. Understanding the mechanism of this reaction, including radical formation and stability, is crucial for predicting the products.
Recommended video:
Guided course
03:09
Acid Catalyzed
Selectivity in Halogenation
Selectivity in halogenation describes the preference of a halogen to react with certain hydrogen atoms over others in a molecule. Factors influencing selectivity include the stability of the resulting radical intermediates and the nature of the halogen used. For example, bromination is generally more selective than chlorination due to the relative stabilities of the radicals formed.
Recommended video:
Guided course
03:45Halogenation Mechanism
Radical Mechanism
The radical mechanism involves the formation of free radicals during the halogenation process. This mechanism typically consists of three steps: initiation, propagation, and termination. Understanding how radicals are generated and how they react with substrates is essential for predicting the major products of monohalogenation reactions.
Recommended video:
Guided course
03:28The mechanism of Radical Polymerization.
Related Practice
Textbook Question
For each of the following acid–base reactions, (i) predict which side of the reaction you expect to be favored. If a pKa is not one of the ten common ones we learned in Chapter 4, it will be given to you.
(a)
1
views
Textbook Question
The radical fluorination of 2-methyl propane resulted in a 14:86 ratio of products.
(b) From the relative reactivity, calculate the difference in energy between the transition states of the first propagation steps leading to a 1° and 3° radical.
1
views
Textbook Question
The following table of strain energies is associated with a variety of 1,2-gauche interactions. Use this table to answer the questions (i)–(iv).
For each of the bond rotations shown, (i) identify which you believe to be more stable, (ii) calculate ∆G°, (iii) calculate the equilibrium constant, and (iv) draw the transition state.
(c)
5
views
Textbook Question
For each of the following acid–base reactions, (iii) calculate ∆G°. If a pKa is not one of the ten common ones we learned in Chapter 4, it will be given to you.
(a)
5
views
Textbook Question
Predict the major monohalogenation product(s) of the following reactions. Indicate whether you think the reaction will be selective and justify your position.
(a)
1
views