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 5d,e
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
Verified step by step guidance1
Analyze the structure of the starting material: The molecule contains two primary alcohol groups (-CH2OH) and one secondary alcohol group (-CHOH). These functional groups are susceptible to oxidation under the given conditions.
Understand the role of DMSO and oxalyl chloride (Swern oxidation): This reagent combination selectively oxidizes primary alcohols to aldehydes and secondary alcohols to ketones without over-oxidizing to carboxylic acids.
Predict the product for DMSO and oxalyl chloride: The primary alcohol group (-CH2OH) on the side chain will be oxidized to an aldehyde (-CHO), and the secondary alcohol group (-CHOH) in the ring will be oxidized to a ketone (-C=O). The hydroxyl group (-OH) on the ring that is not part of an alcohol functional group will remain unchanged.
Understand the role of DMP (Dess-Martin periodinane): DMP is a mild oxidizing agent that also selectively oxidizes primary alcohols to aldehydes and secondary alcohols to ketones, similar to Swern oxidation.
Predict the product for DMP: The primary alcohol group (-CH2OH) on the side chain will be oxidized to an aldehyde (-CHO), and the secondary alcohol group (-CHOH) in the ring will be oxidized to a ketone (-C=O). The hydroxyl group (-OH) on the ring that is not part of an alcohol functional group will remain unchanged.
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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 by a molecule. In organic chemistry, this often pertains to the conversion of alcohols to carbonyl compounds or further to carboxylic acids. Understanding the specific reagents used in oxidation, such as DMSO and periodinane, is crucial for predicting the products formed.
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03:20
Benzylic Oxidation
DMSO and Oxalyl Chloride
DMSO (dimethyl sulfoxide) in combination with oxalyl chloride is a powerful oxidizing system that can convert alcohols to aldehydes or ketones. This reagent pair is particularly effective for transforming primary alcohols into aldehydes without over-oxidation to carboxylic acids, making it essential to recognize the expected product based on the starting material.
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03:13Acid Chloride Nomenclature
DMP (Dess-Martin Periodinane)
DMP, or Dess-Martin periodinane, is a mild and selective oxidizing agent used primarily for the oxidation of alcohols to aldehydes and ketones. It is favored for its ability to perform these transformations under mild conditions, minimizing side reactions. Understanding its selectivity helps in predicting the outcome of oxidation reactions involving various alcohols.
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.
(f) 1-methylcyclohexanol → 2-methylcyclohexanone (several steps)
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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.
a. chromic acid
b. PCC (pyridinium chlorochromate)
c. sodium hypochlorite/acetic acid
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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 (1) Na2Cr2O7/H2SO4, (2) PCC
c. 4-hydroxydecanal
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