Question

Predict the structures of compounds (0) through (VI) and write the curved arrow mechanisms to justify their formation from their precursors. Write each mechanism on a separate sheet of paper. DUE on D2L on: November 7 SOC pont Show Mg1.CO2, CH,OH (excess) conc. H2SO4 (catalytic) III heat anhydrous 2. H2O (ether Show now tracks 1. CHgMgBr (2 eq.) i anhydrous ether 2. H, 1. LiAIH, in anhydrous ether 2. H3O CH3OH (excess) conc. H, SO, (catalytic) PCC in dichloromethane IV VI heat, Dean-Stark Trap

Answer 1

oyi Ni benzoyl chloride SOCI2 COOH MgBr Co. Mg CH3OH Excess Con H2SO4 Ha Ether OCH3 bromobenzene benzoic acid LiAlH4 H30+ CH3MgBr (2 equiv) H2O PCC DH OH CH3OH Excess COn H2SO4 Qoch OCH3 OCH3 benzoic acid was synthesized from bromobenzene. Then SoCl2 gives benzoyl chloride and amide formation occurs. Simulataneously, ester synthesis was perfomed. The ester gives tertiary alcohol using Grignard reagent. At the same time ester gives benzyl alcohol with LiAlH4. The alcohol is oxidized to PCC and then protected with methanol to form acetal.