Domanda del libro di testo
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA
(d)
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Ch. 9 - Alkenes 2: Oxidation and Reduction
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. 9 - Alkenes 2: Oxidation and ReductionProblema 45d(iii)
Mullins 1st EditionCh. 9 - Alkenes 2: Oxidation and ReductionProblema 45d(iii)Capitolo 8, Problema 45d(iii)
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br2, H2O
(d) 
Guida verificata passo dopo passo1
Identify the type of reaction: The reaction involves an alkene reacting with bromine (Br₂) in the presence of water (H₂O). This is an example of a halohydrin formation reaction, where the alkene undergoes an electrophilic addition reaction.
Understand the mechanism: The reaction proceeds via the formation of a bromonium ion intermediate. The π-electrons of the alkene attack a bromine molecule (Br₂), leading to the formation of a three-membered bromonium ion.
Determine the nucleophile: In the presence of water, the water molecule acts as the nucleophile. It attacks the more substituted carbon of the bromonium ion due to the partial positive charge being more stabilized at that position (Markovnikov's rule).
Add the nucleophile: The water molecule opens the bromonium ion ring by attacking the more substituted carbon, leading to the formation of a halohydrin. The hydroxyl group (-OH) attaches to the more substituted carbon, while the bromine atom attaches to the less substituted carbon.
Draw the product: The final product is a halohydrin, where the -OH group and the -Br group are added across the double bond in an anti-addition manner (opposite sides of the former double bond). Ensure stereochemistry is considered if the starting alkene is asymmetric.
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Electrophilic Addition
Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, typically involving alkenes. In the case of alkenes reacting with Br₂, the double bond acts as a nucleophile, attacking the electrophilic bromine molecule, leading to the formation of a cyclic bromonium ion intermediate.
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1,2 vs 1,4 Addition
Bromohydrin Formation
Bromohydrin formation occurs when an alkene reacts with bromine in the presence of water. The bromonium ion intermediate is attacked by water, resulting in the addition of a bromine atom and a hydroxyl group across the double bond, yielding a bromohydrin product. This reaction is stereospecific and can lead to different stereoisomers depending on the alkene's configuration.
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02:26Formation of Enolates
Regioselectivity
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple products are possible. In the reaction of alkenes with Br₂ and H₂O, the regioselectivity is influenced by the stability of the carbocation intermediates formed during the reaction, which can lead to Markovnikov or anti-Markovnikov products depending on the substituents on the alkene.
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05:09Heck Reaction
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