Textbook Question
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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Table of contents
- 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
Chapter 11, Problem 2f
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
Verified step by step guidance1
Step 1: Identify the functional group in 1-phenylpropan-1-ol. The compound contains a primary alcohol (-OH group) attached to a carbon that is part of a propyl chain, which is also connected to a phenyl group (C6H5).
Step 2: Analyze the reaction conditions for (1) chromic acid (H2CrO4) or excess sodium hypochlorite (NaOCl) with acetic acid. Both are strong oxidizing agents that can oxidize primary alcohols to carboxylic acids. The reaction proceeds through the intermediate formation of an aldehyde, which is further oxidized to a carboxylic acid.
Step 3: Predict the product for reaction (1). The primary alcohol group (-CH2OH) in 1-phenylpropan-1-ol will be oxidized to a carboxylic acid group (-COOH), resulting in the formation of 1-phenylpropanoic acid.
Step 4: Analyze the reaction conditions for (2) PCC (pyridinium chlorochromate) or NaOCl (1 equivalent) with TEMPO. These are milder oxidizing agents that selectively oxidize primary alcohols to aldehydes without further oxidation to carboxylic acids.
Step 5: Predict the product for reaction (2). The primary alcohol group (-CH2OH) in 1-phenylpropan-1-ol will be oxidized to an aldehyde group (-CHO), resulting in the formation of 1-phenylpropanal.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
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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Benzylic Oxidation
Oxidizing Agents
Oxidizing agents are substances that facilitate the oxidation of other compounds by accepting electrons. Chromic acid and sodium hypochlorite are strong oxidizers that can convert primary alcohols to carboxylic acids or secondary alcohols to ketones. The choice of oxidizing agent and its conditions (excess or limited) significantly influence the reaction pathway and final products.
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Selective Oxidation
Selective oxidation refers to the ability to oxidize specific functional groups in a molecule without affecting others. For instance, using PCC (Pyridinium chlorochromate) or NaOCl in the presence of TEMPO allows for the selective oxidation of alcohols to aldehydes or ketones, minimizing over-oxidation. This concept is essential for predicting the outcomes of reactions involving complex organic molecules.
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Related Practice
Textbook Question
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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Textbook Question
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
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Textbook Question
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
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Textbook Question
Give the structure of the principal product(s) when each of the following alcohols reacts with (1) Na2Cr2O7/H2SO4, (2) PCC, (3) DMP, and (4) 1 equiv NaOCl-TEMPO.
a. octan-1-ol
b. octan-3-ol
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Textbook Question
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
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