Textbook Question
How does the carbonyl in mCPBA weaken the O―O σ bond (i.e., make a better leaving group)?
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Ch. 9 - Alkenes II: Oxidation and Reduction
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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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
Chapter 8, Problem 13c
Suggest an alkene that could be used to make each of the following halohydrins.
(c) 
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Analyze the structure of the halohydrin provided. The molecule contains a chlorine atom and a hydroxyl group (-OH) attached to adjacent carbons. This suggests that the halohydrin was formed via the addition of Cl₂ and H₂O to an alkene.
Identify the stereochemistry of the halohydrin. The chlorine atom is on a wedge (indicating it is coming out of the plane), and the hydroxyl group is on a dash (indicating it is going into the plane). This anti-addition stereochemistry is characteristic of halohydrin formation.
Determine the location of the double bond in the starting alkene. The double bond must be between the two carbons where the chlorine and hydroxyl groups are now attached. This is because halohydrin formation involves the electrophilic addition of Cl₂ and H₂O across the double bond.
Consider the structure of the alkene. The alkene must have a cyclopentyl group on one side and an isopropyl group on the other side of the double bond to match the substituents in the halohydrin product.
Propose the alkene structure. Based on the analysis, the alkene should be 1-cyclopentyl-1-isopropylethene, with the double bond positioned between the two carbons that now bear the chlorine and hydroxyl groups.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alkenes
Alkenes are hydrocarbons that contain at least one carbon-carbon double bond (C=C). They are unsaturated compounds and can undergo various reactions, including addition reactions, where atoms or groups are added to the carbon atoms of the double bond. Understanding the structure and reactivity of alkenes is crucial for predicting the products of reactions, such as the formation of halohydrins.
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Alkene Metathesis Concept 1
Halohydrin Formation
Halohydrins are compounds formed when alkenes react with halogens and water, resulting in the addition of a halogen atom and a hydroxyl group (OH) across the double bond. This reaction typically occurs via a mechanism involving the formation of a cyclic halonium ion intermediate, which influences the regioselectivity and stereochemistry of the product. Recognizing the mechanism is essential for determining which alkene can yield the desired halohydrin.
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01:44General properties of halohydrin formation.
Regioselectivity
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the context of halohydrin formation, the regioselectivity is influenced by the stability of the carbocation intermediates formed during the reaction. Understanding regioselectivity helps in predicting which alkene will produce the desired halohydrin based on the substitution pattern of the alkene and the nature of the halogen.
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05:09Heck Reaction
Related Practice
Textbook Question
Suggest an alkene that could be used to make each of the following halohydrins.
(a)
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Textbook Question
Calculate the atom economy of the reaction in Figure 9.24. [Catalysts are not included in the atom economy calculation.]
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Textbook Question
Provide arrow-pushing mechanisms for Assessments 9.10(b) and 9.10(c) that rationalize the regioselective and stereospecific formation of each halohydrin.
(b)
(c)
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Textbook Question
Predict the product(s) when each of the following are reacted with mCPBA, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers.
(a)
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Textbook Question
Explain why water attacks the carbon of the bromonium ion as opposed to the bromonium ion itself in the second step of halohydrin formation.
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