Textbook Question
A chemist failed to generate the alcohol using the reaction shown here.
(b) How could the reaction conditions be modified to allow formation of the product?
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Ch. 16 - Metals in Organic Chemistry
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 15, Problem 42
Which of the following solvents are reasonable choices for a Grignard reaction? Justify your choices. [Hint: Carbonyls are good electrophiles.]
Verified step by step guidance1
Grignard reagents are highly reactive organomagnesium compounds that are sensitive to moisture and protic solvents. Therefore, the choice of solvent is crucial for the success of a Grignard reaction.
The first structure is tetrahydrofuran (THF), a cyclic ether. Ethers are generally good solvents for Grignard reactions because they can stabilize the Grignard reagent through coordination with the oxygen atom, and they do not contain acidic protons that would react with the Grignard reagent.
The second structure is ethyl acetate, an ester. Esters are not suitable solvents for Grignard reactions because they contain a carbonyl group, which is a good electrophile and would react with the Grignard reagent, leading to unwanted side reactions.
The third structure is ethanol, an alcohol. Alcohols are protic solvents and contain acidic protons that would react with the Grignard reagent, destroying it. Therefore, ethanol is not a suitable solvent for Grignard reactions.
The fourth structure is diethyl ether, a common solvent for Grignard reactions. Like THF, diethyl ether is an aprotic solvent that can stabilize the Grignard reagent without reacting with it. It is often used in Grignard reactions due to its ability to dissolve both the Grignard reagent and the organic substrate.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Grignard Reagents
Grignard reagents are organomagnesium compounds that are highly reactive and serve as nucleophiles in organic synthesis. They are formed by reacting alkyl or aryl halides with magnesium metal in anhydrous ether. Their reactivity allows them to attack electrophiles, such as carbonyl compounds, making them essential in forming new carbon-carbon bonds.
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Carbonation of Grignard Reagents
Solvent Properties
The choice of solvent in a Grignard reaction is critical because Grignard reagents are sensitive to moisture and can react with protic solvents, leading to their decomposition. Suitable solvents are typically non-polar and aprotic, such as diethyl ether or tetrahydrofuran (THF), which can stabilize the Grignard reagent without participating in the reaction.
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Electrophilicity of Carbonyls
Carbonyl compounds, such as aldehydes and ketones, are good electrophiles due to the polarized carbon-oxygen double bond, where the carbon atom carries a partial positive charge. This makes them susceptible to nucleophilic attack by Grignard reagents, facilitating the formation of alcohols after subsequent hydrolysis. Understanding this reactivity is crucial for predicting the outcomes of Grignard reactions.
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Related Practice
Textbook Question
A chemist failed to generate the alcohol using the reaction shown here.
(a) Suggest a reason why this reaction did not work as written.
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Textbook Question
Predict the product of the following epoxide opening reactions.
(a)
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Textbook Question
Predict the product of the following epoxide opening reactions.
(b)
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Textbook Question
The situation shown here is an example where a cuprate is the only organometallic that will allow the product alcohol to be obtained. What is the problem with using a Grignard or an organolithium to attempt the same reaction?
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Textbook Question
A chemist failed to generate the diol using the reaction shown here.
(a) Suggest a reason why this reaction did not work as written.
(b) How could the reaction conditions be modified to allow formation of the diol? [It may require more than one step.]
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