Textbook Question
Draw the product obtained by heating each pair of ketones in a basic solution.
a.
2
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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 35d
Draw the product of the reaction of each of the following compounds with a base:
d. 
Verified step by step guidance1
Identify the functional group in the compound provided. Determine if the compound contains acidic protons, such as those in alcohols, phenols, carboxylic acids, or alpha-hydrogens adjacent to carbonyl groups, which can react with a base.
Determine the type of base used in the reaction. Strong bases (e.g., hydroxide ion, alkoxide ion) will deprotonate acidic hydrogens, while weaker bases may only partially react.
Locate the most acidic hydrogen in the compound. For example, in alcohols, the hydrogen on the hydroxyl group (-OH) is acidic, while in carbonyl compounds, alpha-hydrogens are acidic due to resonance stabilization of the resulting enolate ion.
Write the deprotonation reaction. Use a curved arrow mechanism to show the base abstracting the acidic proton, resulting in the formation of the conjugate base of the compound and the conjugate acid of the base.
Draw the final product, which is the conjugate base of the original compound. Ensure that the negative charge is placed on the appropriate atom, such as oxygen in alcohols or carbon in enolates, and that resonance structures are considered if applicable.
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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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02:49
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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02:36Identifying Functional Groups
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 and the overall energy changes during the reaction.
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02:16Heck Reaction Mechanism
Related Practice
Textbook Question
Draw the product of the reaction of each of the following compounds with a base:
b.
1
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Textbook Question
What two carbonyl compounds are needed to synthesize each of the following compounds, using a Robinson annulation?
a.
1
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Textbook Question
Draw the product of the reaction of each of the following compounds with a base:
c.
1
views
Textbook Question
Draw the product of the reaction of each of the following compounds with a base:
a.
1
views
Textbook Question
Draw the product obtained by heating each pair of ketones in a basic solution.
b.
2
views