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 45d
Mullins 1st EditionCh. 10 - Alkynes: Electrophilic Addition and Redox ReactionsProblem 45dChapter 9, Problem 45d
Show the products of the following acetylide alkylation reactions. [Make sure your product has the correct number of carbons.]
(d) 
Verified step by step guidance1
Step 1: Recognize the reactants. The starting material is acetylene (H≡H), and the reagents are sodium amide (NaNH₂) and a dibromoalkane. Sodium amide is a strong base used to deprotonate acetylene, forming an acetylide ion.
Step 2: Deprotonation of acetylene. In the first step, NaNH₂ removes a proton from acetylene, generating the acetylide ion (C≡C⁻). This ion is highly nucleophilic and will attack electrophiles in subsequent steps.
Step 3: Analyze the dibromoalkane structure. The dibromoalkane has two bromine atoms attached to a long carbon chain. Bromine atoms are good leaving groups, making the molecule suitable for nucleophilic substitution reactions.
Step 4: Perform the first substitution reaction. The acetylide ion (C≡C⁻) attacks one of the carbon atoms bonded to a bromine atom in the dibromoalkane, displacing the bromine and forming a new carbon-carbon bond. This extends the carbon chain.
Step 5: Perform the second substitution reaction. The newly formed alkylated acetylide ion reacts with the second bromine atom in the dibromoalkane, displacing the bromine and forming another carbon-carbon bond. The final product is a longer alkyne with the correct number of carbons.
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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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Alkylation Reaction
Alkylation is a chemical reaction where an alkyl group is transferred to a nucleophile, such as an acetylide ion. This process typically involves the reaction of the nucleophile with an alkyl halide, leading to the formation of a new carbon-carbon bond. Mastery of this concept is essential for predicting the products of the given reactions.
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Carbon Count in Products
In organic synthesis, it is important to ensure that the product of a reaction has the correct number of carbon atoms, reflecting the starting materials. This concept involves understanding how the number of carbons changes during reactions, particularly in alkylation, where the acetylide ion adds to the carbon chain of the alkyl halide. Keeping track of carbon counts helps verify the accuracy of the reaction products.
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Related Practice
Textbook Question
Show the products of the following acetylide alkylation reactions. [Make sure your product has the correct number of carbons.]
(a)
1083
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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.]
(c)
867
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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
Suggest a method for synthesizing the following alkynes using an alkyne and an alkyl halide. [There are two correct answers for each product.]
(a)
1004
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Textbook Question
Complete the following synthesis by providing the necessary reagents.
948
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