14. Synthetic Techniques
Retrosynthesis
8PRACTICE PROBLEM
Provide the structures of compounds I through VI given the following information: I (C8H13Br) reacts with magnesium in ether to produce II (C8H13MgBr), which then reacts with D2O to give 3-isopropylcyclopent-1-ene with a deuterium atom on the end of the isopropyl group (III). II reacts with butan-2-one (C4H8O) followed by acid work-up, and produces IV (C11H20O). IV is then heated with concentrated H2SO4 to produce V (C11H18), which then reacts with two equivalents of Br2 to give VI (C11H14Br4). V undergoes hydrogenation with excess H2 and Pt catalyst to produce (3-methylpentan-2-yl)cyclopentane. (Ignore stereochemistry)
Provide the structures of compounds I through VI given the following information: I (C8H13Br) reacts with magnesium in ether to produce II (C8H13MgBr), which then reacts with D2O to give 3-isopropylcyclopent-1-ene with a deuterium atom on the end of the isopropyl group (III). II reacts with butan-2-one (C4H8O) followed by acid work-up, and produces IV (C11H20O). IV is then heated with concentrated H2SO4 to produce V (C11H18), which then reacts with two equivalents of Br2 to give VI (C11H14Br4). V undergoes hydrogenation with excess H2 and Pt catalyst to produce (3-methylpentan-2-yl)cyclopentane. (Ignore stereochemistry)