Skip to main content
Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Non è quello che usi tu?Cambia libro di testo
Capitolo 9, Problema 45a

Show the products of the following acetylide alkylation reactions. [Make sure your product has the correct number of carbons.]
(a) Chemical reaction diagram showing acetylide alkylation with reactants and products labeled.

Guida verificata passo dopo passo
1
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.

Risposta video verificata per un problema simile:

Questa soluzione video è stata consigliata dai nostri tutor come utile per risolvere questo problema.
Durata del video:
2m

Concetti chiave

Ecco i concetti essenziali che devi comprendere per rispondere correttamente alla domanda.

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.
Video consigliato:
Percorso guidato
3:39
Metal Ion Catalysis Concept 1

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.
Video consigliato:
01:47
Nucleophiles and Electrophiles can react in Substitution Reactions.

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.
Video consigliato:
07:07
Electron Counting