Textbook Question
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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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 13a(2)
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblem 13a(2)Chapter 17, Problem 13a(2)
Show how the following compounds can be prepared, using ethyne as one of the starting materials:
2. 1-phenyl-2-butyn-1-ol
Verified step by step guidance1
Step 1: Start with ethyne (C₂H₂) as the base molecule. Ethyne is a simple alkyne with a triple bond between two carbon atoms. The goal is to build the desired compound step by step by adding functional groups and extending the carbon chain.
Step 2: Perform a nucleophilic addition reaction to extend the carbon chain. React ethyne with an alkyl halide (e.g., ethyl bromide, CH₃CH₂Br) in the presence of a strong base like sodium amide (NaNH₂). This will result in the formation of 1-butyne (CH≡C-CH₂CH₃).
Step 3: Introduce the phenyl group to the molecule. Use a Friedel-Crafts alkylation reaction or a Grignard reaction to attach a phenyl group (C₆H₅) to the terminal carbon of 1-butyne. This will yield 1-phenyl-1-butyne (C₆H₅-C≡C-CH₂CH₃).
Step 4: Perform a hydroboration-oxidation reaction to convert the terminal alkyne into an alcohol group. Use reagents such as BH₃ (borane) followed by H₂O₂ (hydrogen peroxide) and NaOH (sodium hydroxide). This will produce 1-phenyl-2-butyn-1-ol (C₆H₅-C≡C-CH(OH)-CH₃).
Step 5: Verify the structure of the final product to ensure it matches the desired compound, 1-phenyl-2-butyn-1-ol. Confirm that the phenyl group is attached to the first carbon, the hydroxyl group is on the second carbon, and the triple bond is between the second and third carbons.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ethyne as a Building Block
Ethyne, also known as acetylene, is a simple alkyne that serves as a versatile building block in organic synthesis. Its triple bond allows for various reactions, including addition reactions with electrophiles and nucleophiles, making it a key starting material for constructing more complex molecules.
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Alkyne Reactions
Alkynes undergo a variety of reactions, including hydrohalogenation, hydration, and coupling reactions. Understanding these reactions is crucial for synthesizing compounds like 1-phenyl-2-butyn-1-ol, as they allow for the introduction of functional groups and the formation of carbon-carbon bonds necessary for building the desired structure.
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Functional Group Interconversion
Functional group interconversion involves transforming one functional group into another, which is essential in organic synthesis. In the case of 1-phenyl-2-butyn-1-ol, converting an alkyne to an alcohol through hydration or other methods is a key step, highlighting the importance of understanding how to manipulate functional groups to achieve the target compound.
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Related Practice
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
Show how the following compounds can be prepared, using ethyne as one of the starting materials:
3. 2-methyl-3-hexyn-2-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
Show how the following compounds can be synthesized from cyclohexanol.
a. b. c.
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Textbook Question
Explain why ethyne should be alkylated before, rather than after, nucleophilic addition.
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