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 1g,h,i
Classify each reaction as an oxidation, a reduction, or neither.
(g) 
(h) 
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(i) 
Verified step by step guidance1
Step 1: Analyze reaction (g). The reaction involves the addition of HBr to a cycloalkene. This is an electrophilic addition reaction where the double bond is broken, and a bromine atom is added to one carbon while a hydrogen atom is added to the other. Since there is no change in the oxidation state of the carbons involved, this reaction is classified as 'neither oxidation nor reduction.'
Step 2: Analyze reaction (h). The first step involves dehydration of the alcohol using H2SO4, resulting in the formation of a double bond (alkene). The second step involves hydrogenation of the alkene using H2 and Pt, converting the double bond into a single bond (alkane). The hydrogenation step adds hydrogen atoms to the molecule, reducing the alkene to an alkane. Therefore, this reaction is classified as a 'reduction.'
Step 3: Analyze reaction (i). The reaction involves the addition of OsO4 and H2O2 to a cycloalkene, resulting in the formation of a diol (two hydroxyl groups added to the molecule). This process increases the number of oxygen atoms in the molecule, which is characteristic of an oxidation reaction. Therefore, this reaction is classified as an 'oxidation.'
Step 4: Summarize the classifications: (g) is neither oxidation nor reduction, (h) is a reduction, and (i) is an oxidation.
Step 5: Ensure understanding by reviewing the definitions: Oxidation involves an increase in the number of bonds to oxygen or a decrease in bonds to hydrogen, while reduction involves an increase in bonds to hydrogen or a decrease in bonds to oxygen. Reactions that do not involve changes in oxidation states are classified as 'neither.'
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Oxidation and Reduction
Oxidation refers to the loss of electrons or an increase in oxidation state, while reduction is the gain of electrons or a decrease in oxidation state. In organic chemistry, these processes often involve the addition or removal of oxygen or hydrogen atoms. Understanding these definitions is crucial for classifying reactions correctly.
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00:54
Distinguishing between Oxidation and Reduction
Electrophilic Addition Reactions
Electrophilic addition reactions occur when an electrophile reacts with a nucleophile, typically involving alkenes or alkynes. In the context of the provided reactions, the addition of HBr to an alkene in reaction A illustrates this concept, where the double bond is broken and new bonds are formed with the electrophile and nucleophile.
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05:39Features of Addition Mechanisms.
Hydrogenation
Hydrogenation is a specific type of reduction reaction where hydrogen (H2) is added to a compound, often in the presence of a catalyst like platinum (Pt). In reaction B, the conversion of an alkene to an alkane through hydrogenation exemplifies this process, highlighting the reduction of the carbon-carbon double bond.
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00:48The definition of hydrogenation.
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.
a. cyclohexanol
b. 1-methylcyclohexanol
c. cyclopentylmethanol
2
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Textbook Question
Classify each reaction as an oxidation, a reduction, or neither.
(d)
(e)
(f)
1
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Textbook Question
Classify each reaction as an oxidation, a reduction, or neither.
(a)
(b)
(c)
4
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