bromine, this compound (L1) is treated with magnesium in ether to obtain L2 , which reacts violently with D2O for 1-methyl cyclohexene with a deuterium atom in the methyl group (L3). The L2 reaction is treated with acetone followed by hydrolysis to give L4. Heating L4 with concentrated sulfuric acid gives L5, which decolors the bromine, obtaining L6. L5 undergoes hydrogenation with excess hydrogen and platinum as a catalyst giving rise to isobutyl cyclohexane. Determine the structures of compounds L1 through L6.

bromine, this compound (L1) is treated with magnesium in ether to obtain L2 , which reacts violently with D2O for 1-methyl cyclohexene with a deuterium atom in the methyl group (L3). The L2 reaction is treated with acetone followed by hydrolysis to give L4. Heating L4 with concentrated sulfuric acid gives L5, which decolors the bromine, obtaining L6. L5 undergoes hydrogenation with excess hydrogen and platinum as a catalyst giving rise to isobutyl cyclohexane. Determine the structures of compounds L1 through L6.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.52P: Alcohols are important for organic synthesis, especially in situations involving alkenes. The...

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