Textbook Question
Show the products of the following acetylide alkylation reactions. [Make sure your product has the correct number of carbons.]
(c)
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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 45a
Mullins 1st EditionCh. 10 - Alkynes: Electrophilic Addition and Redox ReactionsProblem 45aChapter 9, Problem 45a
Show the products of the following acetylide alkylation reactions. [Make sure your product has the correct number of carbons.]
(a) 
Verified step by step guidance1
Step 1: Understand the concept of acetylide alkylation. Acetylide ions (R-C≡C⁻) are strong nucleophiles that can attack alkyl halides (R-X) in an SN2 reaction, leading to the formation of a new carbon-carbon bond.
Step 2: Identify the acetylide ion and the alkyl halide in the reaction. The acetylide ion is typically generated from a terminal alkyne (R-C≡CH) by deprotonation using a strong base like NaNH₂ or NaH.
Step 3: Write the mechanism of the SN2 reaction. The acetylide ion attacks the carbon atom bonded to the halogen in the alkyl halide, displacing the halide ion (X⁻) and forming a new bond between the acetylide carbon and the alkyl group.
Step 4: Count the number of carbons in the product. Add the number of carbons in the acetylide ion to the number of carbons in the alkyl halide to ensure the product has the correct number of carbons.
Step 5: Draw the structure of the product. Combine the acetylide group (R-C≡C⁻) with the alkyl group from the alkyl halide, ensuring the triple bond remains intact and the connectivity is correct.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acetylide Ion
An acetylide ion is a negatively charged species formed by deprotonating a terminal alkyne. It is a strong nucleophile, capable of attacking electrophiles in nucleophilic substitution reactions. Understanding how to generate and utilize acetylide ions is crucial for performing alkylation reactions effectively.
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Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the context of acetylide alkylation, the acetylide ion acts as the nucleophile, attacking an alkyl halide to form a new carbon-carbon bond. This process is essential for extending carbon chains in organic synthesis.
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Carbon Count in Products
Maintaining the correct number of carbons in the product is vital in organic synthesis, as it ensures the integrity of the molecular structure. In acetylide alkylation, the number of carbons in the starting materials and the alkyl halide must be accounted for to predict the final product accurately. This concept is crucial for verifying the success of the reaction and understanding the resulting compound's properties.
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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: (v) HCl (2 equiv.). If you expect two products, show both.
(c)
1078
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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)
988
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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)
665
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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)
788
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Textbook Question
For the alkynes shows here, show the product(s) expected to form when treated under the following conditions: (vi) H2SO4, HgSO4, H2O. If you expect two products, show both.
(c)
1121
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