Which Sequence of Reactions Is Expected to Produce the Product

Multiple Choice

Which sequence of reactions is expected to produce the product below as the final, and major, organic product? I 1. HC≡CH, NaNH₂; 2. (CH₃) ₂CHCH₂Br 3. Aqueous H₂SO₄, HgSO₄ II 1. CH₃C≡CH, NaNH₂; 2. (CH₃) ₂CHBr; 3. Disisamylborane; 4. H₂O₂, NaOH
III 1. (CH₃) ₂CHBr, NaNH₂; 2. CH₃C≡CH; 3. O₃; 4. H₂O
IV 1. CH₃C≡CH, NaNH₂: 2. (CH₃) ₂CHCH₂Br; 3. BH₃●THF; 4. H₂O₂, NaOH
V 1) (CH₃) ₂CHCH₂Br, NaNH₂; 2. HC≡CH; 3. 9-BBN; 4. H₂O₂, NaOH

A) I
B) II
C) III
D) IV
E) V