Domanda del libro di testo
How could you prepare the following compound using a starting material that contains no more than three carbons?
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Ch. 17 - Reactions at the Alpha-Carbon
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- 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
Capitolo 17, Problema 25b
Describe how the following compounds can be prepared using an aldol addition in the first step of the synthesis:
b. 
Guida verificata passo dopo passo1
Step 1: Identify the target molecule and recognize the functional groups present. The compound contains a β-hydroxy ketone, which is a typical product of an aldol addition reaction.
Step 2: Determine the two starting materials required for the aldol addition. The β-hydroxy ketone suggests that the reaction involves a ketone and an aldehyde. The ketone group comes from acetone (CH3COCH3), and the aldehyde group comes from benzaldehyde (C6H5CHO).
Step 3: Write the mechanism for the aldol addition reaction. In the presence of a base (e.g., NaOH), acetone undergoes enolate formation. The enolate ion then attacks the carbonyl carbon of benzaldehyde, forming a new C-C bond.
Step 4: After the aldol addition, the intermediate formed is an alkoxide ion. This intermediate is protonated to yield the β-hydroxy ketone product.
Step 5: Verify the structure of the product to ensure it matches the target molecule. The product should have the β-hydroxy ketone functional group and the aromatic ring from benzaldehyde.
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Aldol Addition
Aldol addition is a fundamental reaction in organic chemistry where two carbonyl compounds, typically aldehydes or ketones, react in the presence of a base to form a β-hydroxy aldehyde or ketone. This reaction involves the nucleophilic attack of an enolate ion on the carbonyl carbon of another molecule, leading to the formation of a new carbon-carbon bond. The resulting product can undergo dehydration to yield an α,β-unsaturated carbonyl compound.
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09:51
Crossed Aldol
Enolate Ion Formation
Enolate ions are key intermediates in aldol reactions, formed when a carbonyl compound is deprotonated at the alpha carbon by a base. This results in a resonance-stabilized anion that can act as a nucleophile in subsequent reactions. The stability of the enolate ion is influenced by the structure of the carbonyl compound and the strength of the base used, making it crucial for the efficiency of the aldol addition process.
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02:26Formation of Enolates
Dehydration of Aldol Products
After the aldol addition step, the β-hydroxy carbonyl compound can undergo dehydration, where a molecule of water is eliminated, resulting in the formation of an α,β-unsaturated carbonyl compound. This step is often driven by the stability of the resulting conjugated system and can be facilitated by heat or acid/base conditions. The dehydration product is typically more reactive and can participate in further reactions, making it an important aspect of synthetic pathways.
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09:51Crossed Aldol
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