Which series of reactions described below will result in the formation of compound A, starting with compound B? A) 1. HO-(CH₂)₂-OH /trace H₃O⁺ 2) DMSO (COCl₂)/Et₃N, CH₂Cl₂ 3) MgBr-(CH₂)₂-CH₃/diethyl ether 4) work-up with H₃O⁺ ^{5. PCC} B) 1. PCC 2) SOCl₂ 3) LiCu-((CH₂)₂-CH₃)₂ 4) work-up with H₃O⁺ C) 1. Na₂Cr₂O₇/H₂SO₄ 2) SOCl₂ 3) 2 MgBr-(CH₂)₂-CH₃/diethyl ether 4) work-up with H₃O⁺ D) both A and B E) both B and C

Question

Quizplus · Accepted Answer

The formation of compound A involves the following steps: 1. Protection of hydroxyl group with a sulfonate (HO-(CH₂)₂-OH) 2. Reaction with thionyl chloride and subsequent treatment with DMSO and Et3N leads to formation of the acid chloride (COCl₂). 3. Reaction with magnesium bromide and subsequent workup leads to formation of the corresponding Grignard reagent. 4. Reaction with the sulfonate-protected alcohol and work-up with hydrogen peroxide in pyridine leads to the desired product (compound A). None of the other reaction sequences described would lead to the formation of compound A.

Which Series of Reactions Described Below Will Result in the Formation