Textbook Question
Identify the alkene that would react with Ti(OiPr)₄, (+) -diethyltartrate, and t-butylhydroperoxide to give the following chiral, nonracemic epoxides.
(c)
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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 43a
Calculate the oxidation number for the indicated carbons.
(a) 
Verified step by step guidance1
Identify the carbon atom for which you need to calculate the oxidation number. In organic molecules, this is often indicated by a specific label or context within the problem.
Understand the general rule for calculating oxidation numbers: the oxidation number of a carbon atom is determined by the number of electrons it 'owns' compared to the number of electrons it would own in its elemental state.
Assign oxidation numbers to the atoms directly bonded to the carbon in question. Typically, hydrogen is +1, oxygen is -2, and other carbons are 0. Halogens are usually -1.
Calculate the oxidation number of the carbon atom by considering the bonds it forms. For each bond to a more electronegative atom (like oxygen), subtract 1. For each bond to a less electronegative atom (like hydrogen), add 1. Bonds to other carbons do not affect the oxidation number.
Sum the contributions from each bond to determine the oxidation number of the carbon atom. Remember that the sum of oxidation numbers in a neutral molecule must equal zero, and in an ion, it must equal the charge of the ion.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Oxidation Number
The oxidation number is a theoretical charge assigned to an atom in a molecule, reflecting its electron control relative to a neutral atom. It helps determine the electron transfer in redox reactions. For carbon, it varies based on its bonding with other atoms, especially electronegative ones like oxygen.
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Strong oxidizing agents
Electronegativity
Electronegativity is the tendency of an atom to attract electrons in a chemical bond. It influences the oxidation number calculation, as more electronegative atoms pull electron density away from carbon, increasing its oxidation state. Understanding electronegativity differences is crucial for assigning oxidation numbers accurately.
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Bonding and Structure
The type of bonds and molecular structure around a carbon atom affect its oxidation number. Single, double, or triple bonds, as well as the presence of heteroatoms, alter electron distribution. Analyzing the bonding environment helps determine how electrons are shared or transferred, impacting the oxidation state.
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Related Practice
Textbook Question
Calculate the oxidation number for the indicated carbons.
(c)
1224
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Textbook Question
Calculate the oxidation number for the indicated carbons.
(b)
1327
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Textbook Question
The chiral catalyst (R)-BINAP(COD)RhOTf was used in a hydrogenation reaction as part of the synthesis of fragment C of indinavir. Using the same alkene, predict the product that would be obtained if (S)-BINAP(COD)RhOTf were used instead.
1434
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Textbook Question
Identify the alkene that would react with Ti(OiPr)4, (+) -diethyltartrate, and t-butylhydroperoxide to give the following chiral, nonracemic epoxides.
(b)
585
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Textbook Question
Calculate the oxidation number for the indicated carbons.
(d)
1207
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