Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes
Identify the major product formed in the following reaction sequence:
Correct answer
1
Step-by-step solution
The starting material is 2-(3-bromophenyl)-1,3-dioxolane. The 1,3-dioxolane ring is an acetal, which serves as a protecting group for the aldehyde functionality. Acetals are stable under basic conditions and will not react with Grignard reagents. In the first step, the reaction of the aryl bromide with magnesium (Mg) in ether forms a Grignard reagent. The bromine atom is converted to a -MgBr group, yielding 3-(1,3-dioxolan-2-yl)phenylmagnesium bromide. In the second step, ethanol (EtOH) is added. Grignard reagents