Domanda del libro di testo
Tributyltin hydride (Bu3SnH) is often used as a 'radical carrier' in radical reactions. Which bond would you expect to be weaker, Sn–H or C–H? How might this relate to radical stability? Explain your answer.
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Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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TOC.tableOfContents
- 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 1: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes 2: 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 1: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification 2: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution 1: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution 2: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems 1: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems 2: Pericyclic Reactions54
- Ch. 23 - Benzene 1: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene 2: 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: 9780137566471Non è quello che usi tu?Cambia libro di testo
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Mullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblema 61
Mullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblema 61Capitolo 10, Problema 61
Cyclizations can be carried out under radical conditions involving Bu₃SnH and a catalytic amount of AIBN. Suggest a mechanism for this reaction. [Pay close attention to the bonds formed and broken in developing your mechanism. It may be helpful to number the carbons.]
Guida verificata passo dopo passo1
Begin by understanding the role of AIBN (azobisisobutyronitrile) in the reaction. AIBN is a radical initiator that decomposes upon heating to form nitrogen gas and two 2-cyanoprop-2-yl radicals. These radicals are crucial for initiating the radical chain reaction.
The radical chain reaction starts with the generation of a radical from Bu₃SnH. The 2-cyanoprop-2-yl radical abstracts a hydrogen atom from Bu₃SnH, forming a Bu₃Sn radical.
The Bu₃Sn radical then abstracts the bromine atom from the alkyl bromide substrate, generating an alkyl radical. This step is key as it sets the stage for the cyclization process.
The alkyl radical undergoes intramolecular cyclization by attacking the double bond, forming a new carbon-carbon bond and generating a new radical at the terminal carbon of the double bond.
Finally, the newly formed radical abstracts a hydrogen atom from another molecule of Bu₃SnH, completing the cyclization and regenerating the Bu₃Sn radical, which can continue the chain reaction. The final products are the cyclized compound and Bu₃SnBr.
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Radical Reactions
Radical reactions involve species with unpaired electrons, known as radicals, which are highly reactive. These reactions typically proceed through three main steps: initiation, propagation, and termination. In the context of cyclization, radicals can facilitate the formation of cyclic structures by promoting bond formation between carbon atoms, often leading to the closure of rings.
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03:49
What are Radical Initiators?
Mechanism of Cyclization
Cyclization refers to the process of forming a cyclic compound from a linear precursor. Understanding the mechanism involves identifying the specific steps and intermediates that occur during the reaction. In radical cyclization, the mechanism often includes the generation of a radical species that attacks another part of the molecule, leading to the formation of new bonds and the closure of the ring.
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12:58Monosaccharides - Cyclization
Catalysis in Organic Reactions
Catalysis involves the use of a substance that increases the rate of a chemical reaction without being consumed in the process. In this case, AIBN acts as a radical initiator, facilitating the generation of radicals necessary for the cyclization reaction. Understanding how catalysts influence reaction pathways and mechanisms is crucial for predicting the outcomes of organic reactions.
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Percorso guidato
2:10Introduction to Catalysis Concept 1
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Domanda del libro di testo
Haloalkanes can be reduced to alkanes using radical reactions involving Bu₃SnH and a catalytic amount of AIBN. Suggest a mechanism for this reaction. [Pay close attention to the bonds formed and broken in developing your mechanism.]
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Domanda del libro di testo
A halogenation intended to make compound A formed B instead.
(c) Given the two mechanisms you drew, why might B have formed selectively?
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Domanda del libro di testo
Other molecules can be used as initiators in radical reactions. One such molecule is 2, 2'-azobisisobutyronitrile (AIBN). Show an arrow-pushing mechanism that rationalizes the formation of the following radical species. What are the driving forces of this reaction?
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Domanda del libro di testo
A halogenation intended to make compound A formed B instead.
(a) Suggest a mechanism for the intended formation of A.
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Domanda del libro di testo
A halogenation intended to make compound A formed B instead.
(b) Suggest a mechanism that rationalizes the formation of B.
799
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