Textbook Question
Show how the following compounds can be prepared, using ethyne as one of the starting materials:
2. 1-phenyl-2-butyn-1-ol
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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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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- 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 DerivativesProblem 11
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblem 11Chapter 17, Problem 11
Which of the following compounds does not form an alcohol when it reacts with excess Grignard reagent?
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Identify the functional groups in each compound. For compound A, CH3CH2(C=O)NHCH3, the functional group is an amide (C=O attached to NH). For compound B, CH3CH2(C=O)OCH3, the functional group is an ester (C=O attached to OCH3). For compound C, HOCH2CH2(C=O)OCH3, the functional groups are an ester (C=O attached to OCH3) and an alcohol (OH).
Recall the reactivity of Grignard reagents. Grignard reagents (RMgX) are nucleophiles that react with electrophilic carbonyl groups (C=O) to form alcohols. However, certain functional groups, such as amides, do not react with Grignard reagents because the lone pair on the nitrogen delocalizes into the carbonyl group, reducing its electrophilicity.
Analyze compound A (amide). The carbonyl group in the amide is not electrophilic enough to react with a Grignard reagent due to resonance stabilization. Therefore, compound A will not form an alcohol when reacted with excess Grignard reagent.
Analyze compound B (ester). Esters react with excess Grignard reagent in a two-step process: the first equivalent of Grignard reagent forms a ketone intermediate, and the second equivalent reacts with the ketone to form a tertiary alcohol. Thus, compound B will form an alcohol.
Analyze compound C (ester and alcohol). The ester group in compound C will react with excess Grignard reagent in the same manner as compound B, forming an alcohol. The hydroxyl group (OH) in compound C does not interfere with this reaction. Therefore, compound C will also form an alcohol.
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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 used in organic synthesis to form carbon-carbon bonds. They react with electrophiles, such as carbonyl compounds, to produce alcohols. Understanding their reactivity is crucial for predicting the products of reactions involving these reagents.
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Carbonation of Grignard Reagents
Carbonyl Compounds
Carbonyl compounds contain a carbon atom double-bonded to an oxygen atom (C=O). They are key electrophiles in organic chemistry and can react with Grignard reagents to form alcohols. The nature of the carbonyl compound (e.g., aldehyde, ketone, or ester) influences the outcome of the reaction with Grignard reagents.
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Alcohol Formation
Alcohols are organic compounds characterized by the presence of one or more hydroxyl (-OH) groups. When Grignard reagents react with carbonyl compounds, they typically lead to the formation of alcohols. However, certain functional groups, such as amides or esters, may not yield alcohols upon reaction, which is essential to consider in this question.
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Related Practice
Textbook Question
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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Textbook Question
Show how the following compounds can be prepared, using ethyne as one of the starting materials:
1. 1-pentyn-3-ol
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Textbook Question
Which of the following secondary alcohols can be prepared by the reaction of methyl formate with excess Grignard reagent?
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Textbook Question
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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Textbook Question
Show how the following compounds can be synthesized from cyclohexanol.
a. b. c.
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