Domanda del libro di testo
Predict the products of the reactions of the following compounds with:
1. chromic acid or excess sodium hypochlorite with acetic acid.
2. PCC or NaOCl (1 equivalent) with TEMPO.
d. cyclohexanone
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Ch.11 - Reactions of Alcohols
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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TOC.tableOfContents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Capitolo 11, Problema 2e
Predict the products of the reactions of the following compounds with:
1. chromic acid or excess sodium hypochlorite with acetic acid.
2. PCC or NaOCl (1 equivalent) with TEMPO.
e. cyclohexane
Guida verificata passo dopo passo1
Step 1: Understand the reagents and their roles. Chromic acid (H2CrO4) and sodium hypochlorite (NaOCl) with acetic acid are strong oxidizing agents. They can oxidize primary alcohols to carboxylic acids and secondary alcohols to ketones. PCC (Pyridinium chlorochromate) and NaOCl with TEMPO are milder oxidizing agents. PCC oxidizes primary alcohols to aldehydes and secondary alcohols to ketones, while NaOCl with TEMPO selectively oxidizes primary alcohols to aldehydes.
Step 2: Analyze the structure of cyclohexane. Cyclohexane is a saturated hydrocarbon (alkane) with no functional groups like alcohols or double bonds. Since oxidation reactions typically target functional groups such as alcohols or alkenes, cyclohexane is unlikely to react with these oxidizing agents under normal conditions.
Step 3: Predict the reaction with chromic acid or excess sodium hypochlorite with acetic acid. Since cyclohexane lacks functional groups that can be oxidized, it will remain unreacted in the presence of these strong oxidizing agents.
Step 4: Predict the reaction with PCC or NaOCl (1 equivalent) with TEMPO. Similarly, as cyclohexane does not contain any alcohol groups, it will not undergo oxidation with these milder oxidizing agents.
Step 5: Conclude the analysis. Cyclohexane is inert to the given oxidizing agents because it lacks functional groups that can be oxidized. Therefore, no reaction occurs, and the product remains cyclohexane.
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Oxidation Reactions
Oxidation reactions involve the loss of electrons or an increase in oxidation state of a molecule. In organic chemistry, this often pertains to the conversion of alcohols to carbonyl compounds (aldehydes or ketones) or further to carboxylic acids. Understanding the specific oxidizing agents, such as chromic acid or sodium hypochlorite, is crucial for predicting the products of these reactions.
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03:20
Benzylic Oxidation
Oxidizing Agents
Oxidizing agents are substances that facilitate the oxidation of other compounds by accepting electrons. Chromic acid and sodium hypochlorite are common oxidizing agents used in organic synthesis. Their strength and reactivity can vary, influencing the extent of oxidation and the resulting products, such as whether a primary alcohol is oxidized to an aldehyde or a carboxylic acid.
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03:40Strong oxidizing agents
Selective Oxidation
Selective oxidation refers to the ability to oxidize specific functional groups in a molecule without affecting others. Reagents like PCC (Pyridinium chlorochromate) and TEMPO (2,2,6,6-tetramethylpiperidinyl-1-oxyl) are designed for this purpose, allowing for controlled oxidation of alcohols to aldehydes or ketones. Understanding the selectivity of these reagents is essential for predicting the outcomes of reactions involving complex organic molecules.
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03:20Benzylic Oxidation
Pratica correlata
Domanda del libro di testo
We have covered several oxidants that use a multi-valent atom (Cr, Cl, S, or I) as their active species, going from a higher oxidation state before the oxidation to a lower oxidation state after oxidizing the alcohol. Draw the Lewis structures of the following atoms, before and after the oxidation of an alcohol to a ketone or aldehyde. How many bonds to oxygen does each atom have before and after the oxidation?
a. the Cr in chromic acid
b. the Cl in sodium hypochlorite
c. the S in the Swern oxidation
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Domanda del libro di testo
Classify each reaction as an oxidation, a reduction, or neither.
(j)
(k)
(l)
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Domanda del libro di testo
Predict the products of the reactions of the following compounds with:
1. chromic acid or excess sodium hypochlorite with acetic acid.
2. PCC or NaOCl (1 equivalent) with TEMPO.
f. 1-phenylpropan-1-ol
681
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Domanda del libro di testo
Predict the products of the reactions of the following compounds with:
1. chromic acid or excess sodium hypochlorite with acetic acid.
2. PCC or NaOCl (1 equivalent) with TEMPO.
a. cyclohexanol
b. 1-methylcyclohexanol
c. cyclopentylmethanol
1908
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Domanda del libro di testo
Predict the products of the reactions of the following compounds with:
1. chromic acid or excess sodium hypochlorite with acetic acid.
2. PCC or NaOCl (1 equivalent) with TEMPO.
g. hexan-1-ol
h. acetaldehyde, CH3CHO
868
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