Textbook Question
Draw the product obtained by heating each pair of ketones in a basic solution.
a.
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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 35b
Draw the product of the reaction of each of the following compounds with a base:
b. 
Verified step by step guidance1
Step 1: Identify the functional groups in the compound. The given compound contains two ketone groups (C=O) located on a cyclic structure.
Step 2: Understand the reaction with a base. A base typically abstracts a proton from the most acidic hydrogen in the molecule. In this case, the alpha-hydrogens (hydrogens attached to the carbon adjacent to the carbonyl group) are the most acidic due to resonance stabilization of the resulting enolate ion.
Step 3: Determine the site of deprotonation. The base will abstract an alpha-hydrogen from one of the carbons adjacent to either of the ketone groups, forming an enolate ion. The enolate ion is stabilized by resonance between the oxygen atom and the alpha-carbon.
Step 4: Draw the enolate ion. Represent the resonance structures of the enolate ion formed after deprotonation. One resonance structure will show the negative charge on the oxygen atom, while the other will show the negative charge on the alpha-carbon.
Step 5: Consider the implications of the reaction. The enolate ion formed can act as a nucleophile in subsequent reactions, but for this problem, the focus is on the formation of the enolate ion as the product of the reaction with the base.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acid-Base Reactions
Acid-base reactions involve the transfer of protons (H+) between reactants. In organic chemistry, bases can deprotonate acidic functional groups, leading to the formation of new products. Understanding the strength of acids and bases, as well as their reactivity, is crucial for predicting the outcome of these reactions.
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The Lewis definition of acids and bases.
Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Identifying the functional groups present in the compounds involved in the reaction is essential for determining how they will interact with a base and what products will form.
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Reaction Mechanisms
Reaction mechanisms describe the step-by-step process by which reactants are converted into products. Understanding the mechanism of a reaction helps predict the products formed when a compound reacts with a base, including any intermediates that may be involved. This knowledge is vital for drawing accurate reaction products.
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Related Practice
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Draw the product of the reaction of each of the following compounds with a base:
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