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 7c
Show how you would accomplish the following synthetic
conversions by adding an organolithium reagent to an acid.
(c) pentanoic acid → heptan-3-one
Verified step by step guidance1
Step 1: Understand the reaction mechanism. Organolithium reagents are strong nucleophiles and bases. When added to a carboxylic acid, they first deprotonate the acid to form a carboxylate anion. This step is crucial for the subsequent reaction steps.
Step 2: For part (c), pentanoic acid → heptan-3-one: Add an organolithium reagent, such as propyl lithium (C3H7Li), to pentanoic acid. The carboxylic acid will be deprotonated to form pentanoate anion, and the organolithium reagent will act as a nucleophile in subsequent steps.
Step 3: After forming the carboxylate anion, react it with an electrophile, such as propyl bromide (C3H7Br), to introduce the propyl group. This step involves nucleophilic substitution, leading to the formation of an intermediate ketone.
Step 4: For part (d), phenylacetic acid → 3,3-dimethyl-1-phenylbutan-2-one: Add an organolithium reagent, such as tert-butyl lithium ((CH3)3CLi), to phenylacetic acid. The acid will be deprotonated to form phenylacetate anion, and the organolithium reagent will act as a nucleophile.
Step 5: React the phenylacetate anion with an appropriate electrophile, such as tert-butyl bromide ((CH3)3CBr), to introduce the tert-butyl group. This step involves nucleophilic substitution, leading to the formation of the desired ketone 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 act as strong nucleophiles and are commonly used in organic synthesis to form carbon-carbon bonds. When added to carbonyl compounds or acids, they can facilitate the formation of new carbon chains, making them essential for various synthetic transformations.
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Reagents
Carboxylic Acid Reactivity
Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). They can undergo nucleophilic acyl substitution reactions, where nucleophiles, such as organolithium reagents, attack the carbonyl carbon. This reactivity is crucial for converting carboxylic acids into more complex molecules, such as ketones or alcohols.
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Synthetic Pathways
Synthetic pathways refer to the series of chemical reactions that transform starting materials into desired products. Understanding these pathways is vital for planning synthetic routes in organic chemistry. In the context of the given conversions, identifying the correct sequence of reactions involving organolithium reagents and carboxylic acids is essential for achieving the target compounds.
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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.
(b)
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Textbook Question
Predict the products of the following reactions.
(c) benzyl bromide + sodium cyanide
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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
Predict the products of the following reactions.
(d) product of (c) + cyclopentylmagnesium bromide, then acidic hydrolysis
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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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