Question

using basic reactions and grignard.

Outline a synthesis of the following compound from the compounds below as the only source of carbon incorporated into the final product, and any needed inorganic reagents. 2 OH , CH3 CH3 from 2 OH CH CH3

Answer 1

Reaction 1: Electrophilic addition of HBr to propene to give 2-bromo propane by following Markovnikov's rule HBr Reaction 2: Grignard reagent prepared from 2-bromopropane is treated with methyl acrylate MgBr THF MgBr он THF, - 20 °C methyl acrylate 3-isopropyl-4-methylpent-1-en-3-ol Reaction 3: The tertiary alcohol from the reaction 2 is subjected to hydroboration-oxidation sequence. The resulting diol is treated with PCC where only primary is converted to aldehyde Pyridinium chlorochromate (PCC) 1. B2Hs, THF он он он но 2. H202, NaOH, H20 CH2Cl2 3-hydroxy-3-isopropyl-4-methylpentanal Reaction 4: Propylene is treated with HBr in presence of peroxide to give 1-bromopropane and then it is converted to propylmagnesium bromide HBr Mg H202 THF Reaction 5: The aldehyde form reaction 3 is now treated with the grignard prepared from reaction 4 to give alcohol он MgBr он он THF, - 20 °C 3-isopropyl-2-methyloctane-3,5-diol