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Which of the following compounds does not form an alcohol when it reacts with excess Grignard reagent?
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Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
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
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Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblema 7a
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblema 7aCapitolo 16, Problema 7a
How many stereoisomers are obtained from the reaction of 2-pentanone with ethylmagnesium bromide followed by the addition of dilute acid?
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Identify the reaction type: The reaction involves the addition of ethylmagnesium bromide (a Grignard reagent) to 2-pentanone (a ketone), followed by acidic workup. This is a nucleophilic addition reaction where the Grignard reagent adds to the carbonyl group of the ketone.
Analyze the product structure: The addition of the Grignard reagent to the carbonyl group of 2-pentanone forms a new carbon-carbon bond, resulting in a tertiary alcohol. The carbonyl carbon becomes a stereogenic center (chiral center) because it is bonded to four different groups after the reaction.
Determine the number of stereoisomers: A molecule with one chiral center can have 2n stereoisomers, where n is the number of chiral centers. Since the product has one chiral center, the number of stereoisomers is 21 = 2.
Consider the stereochemistry: The two stereoisomers are enantiomers, which are non-superimposable mirror images of each other. These arise because the Grignard reagent can attack the planar carbonyl group from either the top or bottom face, leading to two possible configurations (R and S) at the chiral center.
Summarize the result: The reaction of 2-pentanone with ethylmagnesium bromide followed by dilute acid produces two stereoisomers, which are enantiomers of each other.
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Stereoisomerism
Stereoisomerism refers to the phenomenon where compounds have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of those atoms. This can lead to different physical and chemical properties. In organic chemistry, stereoisomers include enantiomers and diastereomers, which are crucial for understanding the behavior of chiral molecules.
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Determining when molecules are stereoisomers.
Grignard Reagents
Grignard reagents are organomagnesium compounds that are highly reactive and used in organic synthesis to form carbon-carbon bonds. When 2-pentanone reacts with ethylmagnesium bromide, it undergoes nucleophilic addition, leading to the formation of a tertiary alcohol. The reaction's stereochemistry is influenced by the configuration of the carbon center involved.
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02:12Carbonation of Grignard Reagents
Acid-Catalyzed Hydrolysis
Acid-catalyzed hydrolysis is a reaction where an organic compound reacts with water in the presence of an acid, leading to the formation of alcohols or other functional groups. In the context of the reaction with 2-pentanone, the addition of dilute acid after the Grignard reaction helps to protonate the alkoxide intermediate, resulting in the final alcohol product, which can exhibit stereoisomerism.
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03:09Acid Catalyzed
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