Textbook Question
Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.
(d) phenylacetic acid → 3,3-dimethyl-1-phenylbutan-2-one
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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 7a
Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.
(a) 
Verified step by step guidance1
Step 1: Analyze the starting material and product. The starting material is benzoic acid (C₆H₅COOH), and the product is acetophenone (C₆H₅COCH₃). This transformation involves replacing the carboxylic acid group (-COOH) with a ketone group (-COCH₃).
Step 2: Prepare the organolithium reagent. To introduce the methyl group (-CH₃) in the ketone, use methyl lithium (CH₃Li) as the organolithium reagent. Organolithium reagents are highly nucleophilic and react with electrophilic centers.
Step 3: React the benzoic acid with the organolithium reagent. The carboxylic acid group (-COOH) reacts with CH₃Li to form an intermediate. The acidic proton of the carboxylic acid is replaced by the lithium ion, forming a lithium carboxylate intermediate.
Step 4: Perform a second addition of the organolithium reagent. The lithium carboxylate intermediate reacts further with another equivalent of CH₃Li, leading to the formation of a dianion intermediate. This intermediate undergoes rearrangement to form the ketone product.
Step 5: Quench the reaction. After the organolithium reagent has reacted completely, the reaction mixture is quenched with water or a mild acid to neutralize any remaining reactive species and isolate the acetophenone product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Organolithium Reagents
Organolithium reagents are highly reactive compounds containing a carbon-lithium bond. They are used as strong nucleophiles in organic synthesis, capable of attacking electrophiles such as carbonyls and halides. Their reactivity allows them to form new carbon-carbon bonds, making them essential for various synthetic transformations.
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Reagents
Acid-Base Reactions
In organic chemistry, acid-base reactions involve the transfer of protons (H+) between species. When an organolithium reagent is added to an acid, it can deprotonate the acid, generating a carbanion. This step is crucial for initiating further reactions, as the resulting carbanion can act as a nucleophile in subsequent steps.
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Synthetic Pathways
Synthetic pathways refer to the series of chemical reactions that transform starting materials into desired products. Understanding the mechanism of how organolithium reagents interact with acids is vital for designing efficient synthetic routes. This includes recognizing the intermediates formed and the conditions required for successful conversions.
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Related Practice
Textbook Question
Show how you would accomplish the following synthetic
conversions by adding an organolithium reagent to an acid.
(c) pentanoic acid → heptan-3-one
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Textbook Question
Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.
(b)
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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.
d. 1-methylcyclohexan-1,4-diol
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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 synthesize each compound from starting materials containing no more than six carbon atoms.
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