Question

Bonus: (6 pts) Provide a synthesis for the target molecule using benzene. COH 01 Lo CO2H SM TM

Answer 1

Step1. Is nitration of benzene so we will get nitrobenzene as a product.

NO2 NH2 HNO3 HHO3 H2S04 d 3tep 2 Stcp-s Siep 3 NHuCh COOH Br NONO2 H2S0y BULi Nacmeta Coo NH2 Co29) cubr COOH Step6 Sep- Step s Step 2 MCPBA COOH

Step2. Is reduction of nitrobenzene using Zinc metal and ammonia chloride we will get Aniline as a product.

Step3. Is a nitration of aniline we will get mixture of product with major our desired product 4-nitroaniline.

Step4. Is reduction of 4-nitroaniline so we will get 1,4-diaminobenzene.

Step5. Is Sandmeyer reaction which will give us 1,4-dibromobenzene.

Step6. 1,4-dibromobenezene on treatment with BuLi we will get lithiated benzene on which by bubbling CO2 gas and quaching with HCl we will end up with dicarboxylic acid as a product.

Step7. Is birch reduction carboxylic acid are electron withdrawing group so we will get ipso and para recuced compound.

Step8. Is epoxidation of double bonds using m-chloroperbenzoic acid so we will get our desired product.