Which Sequence of Reactions Is Expected to Produce the Product

question 172

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

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