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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 5
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblema 5Capitolo 16, Problema 5
What products are formed when the following compounds react with CH3MgBr, followed by the addition of dilute acid? Disregard stereoisomers.
a. 
b. 
c. 
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Identify the type of compound in each case. Both compounds (a and b) contain a carbonyl group (C=O), which is highly reactive with Grignard reagents like CH3MgBr. Grignard reagents act as nucleophiles, attacking the electrophilic carbon of the carbonyl group.
For compound (a), CH3CH2(C=O)H (an aldehyde): The CH3MgBr will attack the carbonyl carbon, breaking the π-bond of the C=O group. This forms an alkoxide intermediate. The addition of dilute acid (H3O+) will protonate the alkoxide, resulting in a secondary alcohol.
For compound (b), CH3CH2CH2(C=O)CH3 (a ketone): The CH3MgBr will similarly attack the carbonyl carbon, breaking the π-bond of the C=O group. This forms an alkoxide intermediate. The addition of dilute acid (H3O+) will protonate the alkoxide, resulting in a tertiary alcohol.
Write the general reaction for Grignard reagents with aldehydes and ketones: Aldehyde + R-MgBr → Secondary alcohol (after acid workup); Ketone + R-MgBr → Tertiary alcohol (after acid workup).
Determine the specific products: For (a), the product is CH3CH2CH(OH)CH3 (a secondary alcohol). For (b), the product is CH3CH2CH2C(OH)(CH3)CH3 (a tertiary alcohol).
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Grignard Reagents
Grignard reagents, such as CH3MgBr, are organomagnesium compounds that act as nucleophiles. They readily react with electrophiles, particularly carbonyl compounds, to form alcohols. The carbon atom in the Grignard reagent donates a pair of electrons to the electrophilic carbon in the carbonyl group, leading to the formation of a new carbon-carbon bond.
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02:12
Carbonation of Grignard Reagents
Carbonyl Compounds
Carbonyl compounds, characterized by the C=O functional group, include aldehydes and ketones. In the context of the question, the carbonyl carbon is electrophilic and susceptible to nucleophilic attack by Grignard reagents. The reaction typically results in the formation of an alkoxide intermediate, which can be protonated in a subsequent step to yield an alcohol.
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01:40Defining meso compounds.
Acid Workup
An acid workup is a common procedure following reactions involving Grignard reagents. After the nucleophilic addition, the reaction mixture is treated with dilute acid, which protonates the alkoxide intermediate formed during the reaction. This step is crucial for converting the alkoxide into the corresponding alcohol, completing the transformation of the original carbonyl compound.
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01:31Oxidative Workup Mechanism:
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