uestion 174 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 I II III IV V
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