Question

Et Et (19) ge Br 1. NaCN (20) Br 2. PhMgBr 3. H30* 3. (12 pts) A biochemist, Dr. Tsang, has come to you to ask your assistance to synthesize two isotopically labelled methylsuccinic acids so she could probe an intriguing biosynthetic pathway. The compounds should be specifically labeled with 14C as indicated by *. Due to financial reasons, the source of the isotope is the salt Na14CN. Outline a synthesis that will accomplish this objective. Clearly indicate the reaction conditions for each step. Сн, о CH3 Но, HO OH OH А O B

Answer 1

exta EL Br eH₂cool mechanism 프 СА, Сон ft enledisation 왜 werish Et HBr. CH2 Bry Br a br 1) Na ang S. 2 sephing Br. Nuga c-ph A INH2 e-Ph k -ph Hot H₂o (NH₃ ph B 62H a e-ph. » Nach 11) Phing for 1) Hoof Ph.

L Bri NG EN ald3 Hz of & 14 Hood Red P Brz ch et (cookt) eltz H. V. Z Reaction Br CooEt A Hoo Hoone CH Looft @dilo al kot (1) H3ot, CH Hood -cool. NOW 2nd entz NOCN Haut alta Rede EH2 NS Hooe Brz mo ఉం, CH3 Na Blitz CH NH2 Hooc- Hooc Na en Lahang, kell 2) H₂O 애 HBY (to oc No CN elts HOOG Hool che هماه You can HOOC Root Asot apply this process in the 1st one