Domanda del libro di testo
Show how you would add a Grignard reagent to an ester or a nitrile to synthesize
(c) pentan-2-one.
706
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Ch. 21 - Carboxylic Acid Derivatives
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 21, Problema 28a
Show how you would add a Grignard reagent to an ester or a nitrile to synthesize
(a) 4-phenylheptan-4-ol.
Guida verificata passo dopo passo1
Step 1: Understand the target molecule. The target molecule, 4-phenylheptan-4-ol, is a tertiary alcohol with a phenyl group attached to the fourth carbon. This suggests that a Grignard reagent will react with a carbonyl compound to form the alcohol.
Step 2: Choose the starting material. To synthesize a tertiary alcohol, a Grignard reagent must react with either an ester or a nitrile. In this case, an ester is a suitable choice because it allows for the addition of two alkyl groups from the Grignard reagent.
Step 3: Select the Grignard reagent. The Grignard reagent should provide the phenyl group (C₆H₅) and the appropriate alkyl chain to form the desired product. Use phenylmagnesium bromide (C₆H₅MgBr) as the Grignard reagent.
Step 4: React the ester with the Grignard reagent. The ester (e.g., ethyl butanoate, CH₃CH₂CH₂COOCH₂CH₃) will undergo nucleophilic attack by the Grignard reagent. The first equivalent of the Grignard reagent will form a ketone intermediate, and the second equivalent will react with the ketone to form the tertiary alcohol.
Step 5: Perform the workup. After the reaction is complete, add water or dilute acid to protonate the alkoxide intermediate and isolate the final product, 4-phenylheptan-4-ol.
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Grignard Reagents
Grignard reagents are organomagnesium compounds that act as nucleophiles in organic reactions. They are formed by reacting alkyl or aryl halides with magnesium metal in dry ether. These reagents can react with carbonyl compounds, such as esters and nitriles, to form alcohols after hydrolysis. Understanding their reactivity is crucial for synthesizing complex organic molecules.
Video consigliato:
02:12
Carbonation of Grignard Reagents
Ester Reactivity
Esters are functional groups characterized by a carbonyl (C=O) adjacent to an ether (C-O) group. They can undergo nucleophilic addition reactions, where a Grignard reagent attacks the carbonyl carbon, leading to the formation of a tetrahedral intermediate. This intermediate can then be protonated to yield an alcohol. Recognizing how esters react with Grignard reagents is essential for the synthesis of alcohols like 4-phenylheptan-4-ol.
Video consigliato:
02:39Ester Nomenclature
Nitrile Reactivity
Nitriles contain a carbon triple-bonded to a nitrogen atom and can also react with Grignard reagents. The nucleophilic attack by the Grignard reagent on the carbon of the nitrile leads to the formation of an intermediate that can be hydrolyzed to yield an amine or an alcohol. This reactivity is important for constructing carbon skeletons in organic synthesis, particularly when aiming for specific alcohols.
Video consigliato:
01:01Nitrile Nomenclature
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