Domanda del libro di testo
Show how you would add Grignard reagent to acid chloride or ester to synthesize the following alcohols.
a. Ph3C–OH
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Ch.10 - Structure and Synthesis of Alcohols
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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TOC.tableOfContents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Capitolo 10, Problema 16
Propose a mechanism for the reaction of acetyl chloride with phenylmagnesium bromide to give 1,1-diphenylethanol.
Guida verificata passo dopo passo1
Step 1: Identify the reactants and the product. Acetyl chloride (CH₃COCl) reacts with phenylmagnesium bromide (C₆H₅MgBr) in an ether solvent, followed by hydrolysis with H₃O⁺, to form 1,1-diphenylethanol.
Step 2: Recognize the role of phenylmagnesium bromide as a Grignard reagent. Grignard reagents are nucleophiles that attack electrophilic carbon atoms, such as the carbonyl carbon in acetyl chloride.
Step 3: The first phenylmagnesium bromide molecule attacks the carbonyl carbon of acetyl chloride, breaking the π bond of the C=O group. This forms a tetrahedral intermediate with a negatively charged oxygen atom and a phenyl group attached to the carbon.
Step 4: The chloride ion (Cl⁻) leaves as a good leaving group, resulting in the formation of a ketone intermediate, acetophenone (C₆H₅COCH₃).
Step 5: The second phenylmagnesium bromide molecule attacks the carbonyl carbon of the ketone intermediate, forming another tetrahedral intermediate. Upon hydrolysis with H₃O⁺, the negatively charged oxygen is protonated, yielding the final product, 1,1-diphenylethanol.
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Nucleophilic Addition
Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, leading to the formation of a new bond. In this case, phenylmagnesium bromide acts as a nucleophile, attacking the carbonyl carbon of acetyl chloride, which is an electrophile due to the polarization of the carbon-oxygen double bond.
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08:27
Nucleophilic Addition
Grignard Reagents
Grignard reagents, such as phenylmagnesium bromide, are organomagnesium compounds that are highly reactive and serve as strong nucleophiles. They can react with various electrophiles, including carbonyl compounds, to form alcohols. Understanding their reactivity is crucial for predicting the outcome of reactions involving these reagents.
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02:12Carbonation of Grignard Reagents
Protonation of Alkoxide
After the nucleophilic addition of phenylmagnesium bromide to acetyl chloride, an alkoxide intermediate is formed. This intermediate is then protonated, typically by adding water or an acid, to yield the final alcohol product, 1,1-diphenylethanol. This step is essential for converting the alkoxide into a stable alcohol.
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03:Proton Splitting
Pratica correlata
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Show how you would synthesize following tertiary alcohol by adding an appropriate Grignard reagent to a ketone.
c. 1-ethylcyclopentanol
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Show how you would synthesize following tertiary alcohol by adding an appropriate Grignard reagent to a ketone.
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A formate ester, such as ethyl formate, reacts with an excess of a Grignard reagent to give (after protonation) secondary alcohols with two identical alkyl groups.
(a) Propose a mechanism to show how the reaction of ethyl formate with an excess of allylmagnesium bromide gives, after protonation, hepta-1,6-dien-4-ol.
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Show how you would add Grignard reagent to acid chloride or ester to synthesize the following alcohols.
c. dicyclohexylphenylmethanol
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Show how you would synthesize following tertiary alcohol by adding an appropriate Grignard reagent to a ketone.
d. 2-cyclopentylpentan-2-ol
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