Textbook Question
Which of the following compounds decarboxylates when heated?
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Ch. 17 - Reactions at the Alpha-Carbon
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
Chapter 18, Problem 49c
Draw the products of the following reactions:
c. acetone + LDA/THF: (1) slow addition of ethyl acetate; (2) HCl
Verified step by step guidance1
Step 1: Identify the role of LDA (Lithium Diisopropylamide) in the reaction. LDA is a strong, non-nucleophilic base that is used to deprotonate the alpha-hydrogen of acetone, forming an enolate ion. This enolate is highly nucleophilic and will participate in subsequent reactions.
Step 2: Recognize the slow addition of ethyl acetate. Ethyl acetate is an ester, and its carbonyl group is electrophilic. The enolate ion formed from acetone will attack the carbonyl carbon of ethyl acetate in a nucleophilic addition reaction, forming a new carbon-carbon bond.
Step 3: Understand the intermediate formed after the nucleophilic attack. The product of this step will be a beta-keto ester, where the acetone enolate has added to the ethyl acetate molecule. This intermediate will have both a ketone and an ester functional group.
Step 4: Analyze the role of HCl in the second step. HCl is an acid that will protonate the intermediate, stabilizing it and completing the reaction. This step ensures the final product is neutral and fully formed.
Step 5: Draw the final product. The final product will be a beta-keto ester, specifically ethyl 3-oxobutanoate, formed by the addition of acetone enolate to ethyl acetate followed by protonation with HCl.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Enolate Formation
Enolate formation is a key step in reactions involving carbonyl compounds, where a base abstracts a proton from the alpha carbon, resulting in a resonance-stabilized enolate ion. In this reaction, LDA (Lithium diisopropylamide) acts as a strong base to deprotonate acetone, generating the enolate that can subsequently react with electrophiles like ethyl acetate.
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02:26
Formation of Enolates
Nucleophilic Addition
Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, typically in carbonyl compounds. In this case, the enolate formed from acetone acts as a nucleophile and attacks the carbonyl carbon of ethyl acetate, leading to the formation of a beta-hydroxy carbonyl compound.
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08:27Nucleophilic Addition
Acid Workup
An acid workup is a common procedure in organic synthesis that involves adding an acid, such as HCl, to neutralize the reaction mixture and protonate any basic species. After the nucleophilic addition of the enolate to ethyl acetate, the addition of HCl helps to stabilize the product and convert any remaining enolate or intermediate into the final carbonyl product, facilitating purification.
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01:31Oxidative Workup Mechanism:
Related Practice
Textbook Question
Draw a structure for each of the following: d. the enol tautomer of cyclopentanone
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Textbook Question
Draw the products of the following reactions: e. diethyl malonate: (1) sodium ethoxide; (2) isobutyl bromide; (3) HCl, H2O + heat
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Textbook Question
The 1H NMR chemical shifts of nitromethane, dinitromethane, and trinitromethane are at δ6.10, δ4.33, and δ7.52. Match each chemical shift with the compound. Explain how chemical shift correlates with pKa.
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Textbook Question
Draw the products of the following reactions:
a. diethyl heptanedioate: (1) sodium ethoxide; (2) HCl
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Textbook Question
Draw the products of the following reactions: b. pentanoic acid + PBr3 + Br2, followed by hydrolysis
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