Predict the major product(s) for the reaction of pent-1-en-4-yne with sodium amide followed by reaction with bromoethane.
A) hept-1-en-4-yne
B) hept-6-en-3-yne
C) hept-3-en-6-yne
D) hept-4-en-1-yne
E) hept-2-en-4-yne

Question

Quizplus · Accepted Answer

Sodium amide is a strong base that abstracts a proton from the terminal alkyne, generating a nucleophile that can undergo nucleophilic substitution with bromoethane, resulting in a chain extension by two carbons. The product retains the positions of the double and triple bonds relative to the original molecule, leading to hept-1-en-4-yne.

Predict the Major Product(s) for the Reaction of Pent-1-En-4-Yne with Sodium