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Would you expect but-2-ene or 2-methylbut-2-ene to react more quickly with HBr?
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Ch. 8 - Alkenes 1: Properties and Electrophilic Additions
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. 8 - Alkenes 1: Properties and Electrophilic AdditionsProblema 35b
Mullins 1st EditionCh. 8 - Alkenes 1: Properties and Electrophilic AdditionsProblema 35bCapitolo 7, Problema 35b
Provide the expected product for the reaction of each of the following alkenes with (i) HBr and (ii) HBr, H2O2
(b) 
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Identify the structure of the alkene involved in the reaction. Alkenes are hydrocarbons with a carbon-carbon double bond, which is the site of reactivity in these reactions.
For the reaction with HBr alone, apply Markovnikov's rule. This rule states that in the addition of HX (where X is a halogen) to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached, and the halogen will attach to the carbon with fewer hydrogen atoms. This results in the formation of the more stable carbocation intermediate.
Draw the intermediate carbocation formed after the initial addition of HBr to the alkene. Consider the stability of the carbocation, as tertiary carbocations are more stable than secondary, which are more stable than primary.
For the reaction with HBr and H₂O₂, apply anti-Markovnikov's rule. In the presence of peroxides, the addition of HBr to an alkene proceeds via a radical mechanism, where the bromine atom attaches to the carbon with more hydrogen atoms, opposite to Markovnikov's rule.
Draw the expected product for each reaction, considering the regioselectivity (Markovnikov vs. anti-Markovnikov) and the mechanism (ionic vs. radical) involved in each case.
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Markovnikov's Rule
Markovnikov's Rule states that in the addition of HX (where X is a halogen) to an alkene, the hydrogen atom will attach to the carbon with more hydrogen atoms, and the halogen will attach to the carbon with fewer hydrogen atoms. This rule helps predict the major product in the absence of peroxides.
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The 18 and 16 Electron Rule
Anti-Markovnikov Addition
Anti-Markovnikov addition occurs when HBr is added to an alkene in the presence of peroxides (H₂O₂). The reaction proceeds via a radical mechanism, resulting in the bromine atom attaching to the less substituted carbon, opposite to Markovnikov's Rule, due to the influence of the radical initiator.
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02:43Anti-Markovnikov addition of alcohols to terminal alkynes yields aldehydes
Radical Mechanism
A radical mechanism involves the formation of free radicals, which are highly reactive species with unpaired electrons. In the presence of peroxides, the addition of HBr to alkenes follows a radical pathway, leading to anti-Markovnikov products. Understanding this mechanism is crucial for predicting product formation in peroxide-mediated reactions.
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03:28The mechanism of Radical Polymerization.
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