Question

4) Complete the following synthesis using the indicated starting materials. Products with significant amounts of impurities and/or minor products will be penalized accordingly. All necessary reagents and any conditions (heat, excess, etc) must be shown. (18 pts) Below are some previous chapter reagents that MAY be necessary. Na Cr2O7 or POC 1) Hg(OAc)2, H2O 2) NaBH, NaOH 1) BH3, THE 2) H2O2, NaOH SOCI2 or PBrz t-Buo or LDA

Answer 1

5 - Joma Jose t-Buo HNO3/H2SO4 OTS NO2 Sn/HCI COOH Na2Cr207 NaNO2/HCI KI/H2O TNH2 The starting material is treated t-BuO to give aryl ring. Then it is nitrated to obtain both ortho and para substituted product. But these mixture can be separated by column chromatography and reduced by Sn/HCl. The resulting product is diazotized and treated with Kl. Finally, the compound was oxidized by Na2Cr2O7 to give desired product.