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
1
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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 2a,b,c
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
Verified step by step guidance1
Step 1: Understand the role of the oxidizing agents. Chromic acid (H2CrO4) and excess sodium hypochlorite (NaOCl) with acetic acid are strong oxidizing agents that can oxidize primary alcohols to carboxylic acids and secondary alcohols to ketones. PCC (pyridinium chlorochromate) and NaOCl with TEMPO are milder oxidizing agents that typically oxidize primary alcohols to aldehydes and secondary alcohols to ketones.
Step 2: Analyze the structure of cyclohexanol (a). Cyclohexanol is a secondary alcohol. When treated with chromic acid or excess NaOCl with acetic acid, it will be oxidized to cyclohexanone, a ketone. Similarly, PCC or NaOCl with TEMPO will also oxidize cyclohexanol to cyclohexanone.
Step 3: Examine 1-methylcyclohexanol (b). This compound is a secondary alcohol due to the hydroxyl group (-OH) attached to a carbon that is bonded to two other carbons. Both strong oxidizing agents (chromic acid or excess NaOCl with acetic acid) and mild oxidizing agents (PCC or NaOCl with TEMPO) will oxidize 1-methylcyclohexanol to 1-methylcyclohexanone, a ketone.
Step 4: Consider cyclopentylmethanol (c). Cyclopentylmethanol is a primary alcohol because the hydroxyl group is attached to a carbon bonded to only one other carbon. Strong oxidizing agents (chromic acid or excess NaOCl with acetic acid) will oxidize cyclopentylmethanol to cyclopentylcarboxylic acid, a carboxylic acid. Mild oxidizing agents (PCC or NaOCl with TEMPO) will oxidize cyclopentylmethanol to cyclopentylcarbaldehyde, an aldehyde.
Step 5: Summarize the expected products. For cyclohexanol (a), the product is cyclohexanone regardless of the oxidizing agent. For 1-methylcyclohexanol (b), the product is 1-methylcyclohexanone regardless of the oxidizing agent. For cyclopentylmethanol (c), the product is cyclopentylcarboxylic acid with strong oxidizing agents and cyclopentylcarbaldehyde with mild oxidizing agents.
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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 carboxylic acids. Understanding the specific oxidizing agents, such as chromic acid or PCC, is crucial as they dictate the extent of oxidation and the resulting products.
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Reactivity of Alcohols
Alcohols can undergo various reactions based on their structure and the reagents used. Primary, secondary, and tertiary alcohols react differently with oxidizing agents. For instance, primary alcohols can be oxidized to aldehydes or carboxylic acids, while secondary alcohols typically yield ketones. Recognizing the type of alcohol is essential for predicting the products of the reactions.
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Selectivity of Oxidizing Agents
Different oxidizing agents exhibit varying selectivity in their reactions with alcohols. For example, PCC is a mild oxidant that selectively oxidizes primary alcohols to aldehydes without further oxidation to carboxylic acids, while chromic acid is a stronger oxidant that can fully oxidize primary alcohols to carboxylic acids. Understanding these nuances helps in accurately predicting the products formed in the reactions.
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Related Practice
Textbook Question
Classify each reaction as an oxidation, a reduction, or neither.
(j)
(k)
(l)
2
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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
1
views
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.
f. 1-phenylpropan-1-ol
1
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Textbook Question
Classify each reaction as an oxidation, a reduction, or neither.
(g)
(h)
(i)
3
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Textbook Question
Classify each reaction as an oxidation, a reduction, or neither.
(d)
(e)
(f)
1
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