Textbook Question
Give the structure of the principal product(s) when each of the following alcohols reacts with (1) Na2Cr2O7/H2SO4, (2) PCC
d. 1-methylcyclohexan-1,4-diol
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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 5a,b,c
Predict the products you expect when the following starting material undergoes oxidation with an excess of each of the reagents shown below.
a. chromic acid
b. PCC (pyridinium chlorochromate)
c. sodium hypochlorite/acetic acid
Verified step by step guidance1
Step 1: Analyze the structure of the starting material. The molecule contains multiple hydroxyl (-OH) groups, including primary, secondary, and tertiary alcohols. Each reagent will oxidize these alcohols differently based on their chemical properties.
Step 2: For chromic acid (H2CrO4), it is a strong oxidizing agent. Primary alcohols are oxidized to carboxylic acids, and secondary alcohols are oxidized to ketones. Tertiary alcohols generally do not undergo oxidation under these conditions. Identify the primary and secondary alcohols in the structure and predict their oxidation products.
Step 3: For PCC (pyridinium chlorochromate), it is a milder oxidizing agent. Primary alcohols are oxidized to aldehydes, and secondary alcohols are oxidized to ketones. Tertiary alcohols remain unaffected. Determine which alcohols in the structure will react and predict their products.
Step 4: For sodium hypochlorite (NaOCl) in acetic acid, it is a strong oxidizing agent similar to chromic acid. Primary alcohols are oxidized to carboxylic acids, and secondary alcohols are oxidized to ketones. Tertiary alcohols do not react. Identify the primary and secondary alcohols in the structure and predict their oxidation products.
Step 5: Summarize the expected products for each reagent based on the oxidation reactions described. Ensure that the products are consistent with the functional groups present in the starting material and the reactivity of the reagents.
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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 in organic chemistry involve the loss of electrons or an increase in oxidation state, often resulting in the addition of oxygen or the removal of hydrogen. Common oxidizing agents include chromic acid and PCC, which can convert alcohols into carbonyl compounds. Understanding the specific conditions and mechanisms of these reactions is crucial for predicting the products formed.
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Types of Alcohols
Alcohols can be classified as primary, secondary, or tertiary based on the carbon atom to which the hydroxyl (-OH) group is attached. This classification affects their reactivity during oxidation. For instance, primary alcohols typically oxidize to aldehydes, while secondary alcohols can be oxidized to ketones, and tertiary alcohols are resistant to oxidation under mild conditions.
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Reactivity of Oxidizing Agents
Different oxidizing agents have varying strengths and selectivities. Chromic acid is a strong oxidizer that can fully oxidize primary alcohols to carboxylic acids, while PCC is milder and typically oxidizes primary alcohols to aldehydes without further oxidation. Sodium hypochlorite in acetic acid can also oxidize alcohols, but its mechanism and products can differ, making it essential to understand the specific reagents used in the reaction.
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Related Practice
Textbook Question
Suggest the most appropriate method for each of the following laboratory syntheses. In each case, suggest both a chromium reagent and a chromium-free reagent.
(a) butan-1-ol → butanal, CH3CH2CH2CHO
(b) but-2-en-1-ol → but-2-enoic acid, CH3CH=CH–COOH
(c) butan-2-ol → butan-2-one, CH3COCH2CH3
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Textbook Question
Suggest the most appropriate method for each of the following laboratory syntheses. In each case, suggest both a chromium reagent and a chromium-free reagent.
(d) cyclopentanol → 1-ethylcyclopentanol (two steps)
(e) cyclopentylmethanol → 1-cyclopentylpropan-1-ol (two steps)
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Textbook Question
Give the structure of the principal product(s) when each of the following alcohols reacts with (3) DMP, and (4) 1 equiv NaOCl-TEMPO.
c. 4-hydroxydecanal
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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
c. 4-hydroxydecanal
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Textbook Question
Predict the products you expect when the following starting material undergoes oxidation with an excess of each of the reagents shown below.
d. DMSO and oxalyl chloride
e. DMP (periodinane) reagent
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