Textbook Question
Draw the product of the reaction of each of the following compounds with a base:
d.
1
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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 35a
Draw the product of the reaction of each of the following compounds with a base:
a. 
Verified step by step guidance1
Identify the functional groups in the compound. The structure contains two carbonyl groups: one is a ketone (cyclohexanone) and the other is an ester (ethyl acetate).
Determine the reactivity of each functional group with a base. Bases typically abstract acidic protons, and the most acidic proton in this molecule is the alpha-hydrogen adjacent to the ketone group.
Recognize that the alpha-hydrogen is acidic due to resonance stabilization of the resulting enolate ion. When the base abstracts the alpha-hydrogen, the negative charge on the alpha-carbon can delocalize onto the oxygen atom of the ketone group.
Draw the enolate ion formed after the base abstracts the alpha-hydrogen. Represent the resonance structures to show the delocalization of the negative charge between the alpha-carbon and the oxygen atom of the ketone.
Consider the ester group. While it also has alpha-hydrogens, they are less acidic compared to the alpha-hydrogens of the ketone. Therefore, the reaction primarily occurs at the ketone's alpha-carbon, forming the enolate ion.
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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 be formed.
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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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