Textbook Question
Show the products of the following acetylide alkylation reactions. [Make sure your product has the correct number of carbons.]
(a)
1
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Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions
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
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Mullins 1st EditionCh. 10 - Alkynes: Electrophilic Addition and Redox ReactionsProblem 45c
Mullins 1st EditionCh. 10 - Alkynes: Electrophilic Addition and Redox ReactionsProblem 45cChapter 9, Problem 45c
Show the products of the following acetylide alkylation reactions. [Make sure your product has the correct number of carbons.]
(c) 
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Identify the reactants in the acetylide alkylation reaction. Acetylide ions are strong nucleophiles formed by deprotonating terminal alkynes with a strong base, such as NaNH₂. The alkyl halide provides the electrophile for the reaction.
Determine the structure of the acetylide ion. The acetylide ion is formed by removing the terminal hydrogen from the alkyne, leaving a negatively charged carbon triple-bonded to another carbon.
Analyze the alkyl halide used in the reaction. The alkyl halide should be a primary or methyl halide to avoid side reactions such as elimination. Secondary or tertiary alkyl halides are less suitable for this reaction.
Write the mechanism of the reaction. The acetylide ion attacks the carbon atom of the alkyl halide in an SN2 reaction, displacing the halide ion (leaving group) and forming a new carbon-carbon bond.
Combine the acetylide ion and the alkyl group from the alkyl halide to determine the product. Ensure the product has the correct number of carbons by adding the carbons from the acetylide ion and the alkyl halide together.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acetylide Ions
Acetylide ions are negatively charged species formed by deprotonating terminal alkynes. They are strong nucleophiles, capable of attacking electrophiles in nucleophilic substitution reactions. Understanding their formation and reactivity is crucial for predicting the products of alkylation reactions.
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Alkylation Reactions
Alkylation reactions involve the transfer of an alkyl group from one molecule to another, typically through nucleophilic substitution. In the context of acetylide alkylation, the acetylide ion attacks a primary alkyl halide, resulting in the formation of a new carbon-carbon bond. This process is essential for building larger carbon skeletons in organic synthesis.
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Carbon Count in Products
Maintaining the correct number of carbons in the product is vital in organic chemistry. When performing acetylide alkylation, the total number of carbon atoms in the starting materials must equal the total in the products. This concept ensures that the reaction adheres to the law of conservation of mass and helps in verifying the accuracy of the proposed products.
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Related Practice
Textbook Question
For the alkynes shows here, show the product(s) expected to form when treated under the following conditions: (ix) Br2 (2 equiv.). If you expect two products, show both.
(f)
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Textbook Question
Show the products of the following acetylide alkylation reactions. [Make sure your product has the correct number of carbons.]
(d)
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Textbook Question
Show the products of the following acetylide alkylation reactions. [Make sure your product has the correct number of carbons.]
(b)
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Textbook Question
Suggest a method for synthesizing the following alkynes using an alkyne and an alkyl halide. [There are two correct answers for each product.]
(a)
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Textbook Question
Complete the following synthesis by providing the necessary reagents.
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