Which of the following sequences converts 2-methylpropene and sodium acetylide into 3-methylbutanal? A) 1. HBr; 2. NaCCH; 3. O₃; 4. H₂O B) 1. HBr; 2. NaCCH; 3. O₃; 4. DMS C) 1. HBr, ROOR; 2. NaCCH; 3. O₃; 4. H₂O D) 1. HBr, ROOR; 2. NaCCH; 3. H₂/Ni₂B 4. O₃; 5. DMS E) 1. NaCCH; 2. H₂/Ni₂B; 3. O₃; 4. DMS

Question

Quizplus · Accepted Answer

The correct sequence includes HBr and ROOR in the first step, which converts 2-methylpropene to 2-bromoisobutane. The second step involves reaction with sodium acetylide, which replaces the bromine atom with the acetylide group, forming 3-methyl-1-butyne. The third step is a typical nucleophilic addition of water across the triple bond, forming 3-methyl-2-buten-1-ol. The fourth step involves oxidation with PCC or a similar reagent, which converts the alcohol group to an aldehyde, forming 3-methylbutanal. Since option D is the only one that includes HBr and ROOR in the first step, it is the correct choice.

Which of the Following Sequences Converts 2-Methylpropene and Sodium Acetylide