Question

solve the road mab

16. ROAD MAP: Compounds A, B, and Care constitutional isomers. Treatment of A or B with potassium tert-butoxide gives the same alkene D. If the base is changed to a less sterically hindered base such as sodium ethoxide, A and C give the same alkene E as the major product. Treatment of C (spectroscopic data given on next page) with potassium tert-butoxide gives yet another alkene F as a minor product. Compound B reacts the faster with NaCN than C in DMSO while compound A fails to react with NaCN. Alkene E is more stable than alkene D and F. Give structures of A-F. [12 points] No Reaction NaCN DMSO miz - 106, 108 (3:1) 'H NMR, "'C NMR provided KI To na kot kot

with explanation

Answer 1

14Nma of compound ti - 23.4 pentet, £14) 481.55 (di 31, ci 81.96m, 1 14) مودالی - 553 -----7525 - 5 Nag X C- 10 + BO CE cal (major) (cles stable) (less stable) (morestable) more substituted - is 10 alkyl hale.de : Breacts fast with Naw than a