Textbook Question
Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.
(b)
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Ch. 18 - Ketones and Aldehydes
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 18, Problem 4d(3,4)
Give the structure of the principal product(s) when each of the following alcohols reacts with (3) DMP and (4) 1 equiv NaOCl-TEMPO.
d. 1-methylcyclohexan-1,4-diol
Verified step by step guidance1
Step 1: Understand the reagents involved in the reaction. DMP (Dess-Martin Periodinane) is a mild oxidizing agent that selectively oxidizes primary alcohols to aldehydes and secondary alcohols to ketones. NaOCl-TEMPO is another oxidizing system that can oxidize alcohols, typically primary alcohols to aldehydes and secondary alcohols to ketones.
Step 2: Analyze the structure of the given alcohol, 1-methylcyclohexan-1,4-diol. This molecule contains two hydroxyl (-OH) groups: one at the 1-position (attached to a tertiary carbon) and another at the 4-position (attached to a secondary carbon). The tertiary alcohol at the 1-position is resistant to oxidation under these conditions, while the secondary alcohol at the 4-position is susceptible to oxidation.
Step 3: Predict the reaction with DMP. DMP will oxidize the secondary alcohol at the 4-position to a ketone, leaving the tertiary alcohol at the 1-position unchanged. The resulting product will be 1-methylcyclohexan-1-4-one.
Step 4: Predict the reaction with NaOCl-TEMPO. Similar to DMP, NaOCl-TEMPO will oxidize the secondary alcohol at the 4-position to a ketone, leaving the tertiary alcohol at the 1-position unchanged. The resulting product will again be 1-methylcyclohexan-1-4-one.
Step 5: Summarize the principal product(s). In both cases (reaction with DMP and NaOCl-TEMPO), the principal product is the same: 1-methylcyclohexan-1-4-one. This is due to the selective oxidation of the secondary alcohol at the 4-position while the tertiary alcohol at the 1-position remains unaffected.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Oxidation of Alcohols
Alcohols can undergo oxidation to form carbonyl compounds, such as aldehydes or ketones. The extent of oxidation depends on the reagents used; for instance, DMP (Dess-Martin periodinane) is a mild oxidizing agent that selectively converts primary and secondary alcohols to aldehydes and ketones, respectively, without over-oxidizing them to carboxylic acids.
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Strong oxidizing agents
DMP as an Oxidizing Agent
Dess-Martin periodinane (DMP) is a popular reagent in organic chemistry for the oxidation of alcohols. It is favored for its ability to oxidize alcohols to carbonyls under mild conditions, minimizing side reactions. Understanding how DMP interacts with different alcohols is crucial for predicting the structure of the resulting products.
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NaOCl-TEMPO Oxidation
The combination of sodium hypochlorite (NaOCl) and TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl) is used for the selective oxidation of alcohols to carbonyl compounds. This method is particularly useful for secondary alcohols and can provide high yields of ketones. Recognizing the reactivity of the alcohol in question with this reagent is essential for determining the principal product.
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Related Practice
Textbook Question
Why were no products from the McLafferty rearrangement observed in the spectrum of butan-2-one (Figure 18-3)?
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Textbook Question
Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.
(a)
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Textbook Question
Draw the structure for each of the following:
c. 3-benzylpentane
d. bromomethylbenzene
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Textbook Question
Give the IUPAC name and (if possible) a common name for each compound.
(c)
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Textbook Question
Show how you would synthesize each compound from starting materials containing no more than six carbon atoms.
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