Textbook Question
Rationalize the ranking of increasing reaction rate of the benzylic halides shown.
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Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring
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
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Mullins 1st EditionCh. 24 - Benzene II: Reactions Influenced by the Aromatic RingProblem 53
Mullins 1st EditionCh. 24 - Benzene II: Reactions Influenced by the Aromatic RingProblem 53Chapter 23, Problem 53
Identify the aromatic product that would result from the oxidation of the triol with an excess of PCC.
Verified step by step guidance1
Identify the functional groups present in the starting material. The compound is a triol, meaning it has three hydroxyl (OH) groups attached to a cyclohexane ring.
Understand the role of PCC (Pyridinium Chlorochromate) in oxidation reactions. PCC is a mild oxidizing agent that can oxidize primary alcohols to aldehydes and secondary alcohols to ketones without further oxidation to carboxylic acids.
Consider the structure of the triol. The hydroxyl groups are attached to a cyclohexane ring, which can be oxidized to form carbonyl groups (either aldehydes or ketones).
Recognize that the presence of excess PCC suggests that all oxidizable alcohol groups will be converted to carbonyl groups. In this case, the triol will be oxidized to a compound with three carbonyl groups.
Determine the final structure. The oxidation of the triol with excess PCC will result in the formation of a compound with three ketone groups, which can undergo further rearrangement to form an aromatic compound, such as a quinone, due to the stabilization provided by the aromaticity.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Oxidation with PCC
Pyridinium chlorochromate (PCC) is a reagent used to oxidize alcohols to carbonyl compounds. In excess, PCC can further oxidize primary alcohols to carboxylic acids and secondary alcohols to ketones. Understanding the role of PCC in transforming hydroxyl groups is crucial for predicting the final aromatic product in this reaction.
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05:53
Strong oxidizing agents
Aromaticity
Aromatic compounds are characterized by their cyclic, planar structure with conjugated pi electrons following Huckel's rule (4n+2 pi electrons). The transformation of the triol into an aromatic product involves the formation of a stable, conjugated ring system. Recognizing the conditions that lead to aromaticity is essential for identifying the final product.
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Triol Structure
A triol is a molecule containing three hydroxyl groups. In the given structure, these groups are attached to a cyclohexane ring. The oxidation process will convert these hydroxyl groups into carbonyl groups, facilitating the formation of an aromatic compound. Understanding the initial structure helps in predicting the changes during the reaction.
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Related Practice
Textbook Question
A chemist attempted to oxidize a primary alcohol to a carboxylic acid using chromic acid. The product shown was obtained as a major component in the mixture. Suggest an arrow-pushing mechanism that accounts for its formation. [Think about what chromic acid would normally do to a phenol and make a list of bonds formed and bonds broken.]
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Textbook Question
Phenol oxidation can be coupled with other reactions to form new C―C bonds using reactions studied previously. Predict the product of the following series of reactions.
(a)
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Textbook Question
In Chapter 23, we learned about the electrophilic aromatic nitration reaction. When phenol is subjected to these conditions with a large excess of nitric acid, a molecule called picric acid is produced. Predict the product of this reaction and explain why the pKa value of this compound is 0.38.
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Textbook Question
Rationalize the fact that 1,4-dihydroxybenzene melts at a significantly higher temperature than 1,2-diydroxybenzene.
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Textbook Question
In light of your answers to Assessments 24.54 and 24.55, rank the following based on the rate of protonation of the alkene (1 = most basic, 6 = least basic). [Ignore the fact that the alkene may not be the most basic site in the molecule.]
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