Which of the following effectively produces 4,4-dimethyl-2-pentyne?
A) I, II, III, and IV
B) II, III, and IV
C) I, II, and III
D) I, II, and IV
E) I, III, and IV

Question

Which of the following effectively produces 4,4-dimethyl-2-pentyne? 
A) I, II, III, and IV 
B) II, III, and IV 
C) I, II, and III 
D) I, II, and IV 
E) I, III, and IV

Quizplus · Accepted Answer

II effectively produces 4,4-dimethyl-2-pentyne via the reaction between 1,5-hexadiene and dimethyl acetylenedicarboxylate in the presence of sodium ethoxide. III and IV both involve the reaction of 4,4-dimethyl-2-pentene with hydrogen bromide to form 4,4-dimethyl-2-bromopentane, followed by treatment with sodium ethoxide to form 4,4-dimethyl-2-pentyne. Option I involves the reaction of 2-bromopentane with sodium amide to form 4,4-dimethyl-2-pentyne, but this reaction is less efficient than the methods used in II, III, and IV.

Which of the Following Effectively Produces 4,4-Dimethyl-2-Pentyne