Question

Please show all of your steps. Thank you!

5 (20 pts). (a) Propose a reasonable synthesis, using indicated diketone as starting material. ini ² and any C4 or less starting materials (SMS) (any reagents are allowed) Hint: as a C3 SM use Br (b) Propose two syntheses, which will use two distinct methods for construction of the 6-membered ring: (1) Crossed-Claisen condensation and (2) Claisen condensation(s). must use this reagent plus any acyclic Cg or less BONUS (5 pts). In the following transformation, base (B:) is sufficiently strong to form enolate anions. Propose 1. B: a curved arrow (base) mechanism. Hint: Number the C's, 2. workup and then identify in the product the two C-C bonds formed.

Answer 1

a) i A NaOH. NaOH 2) ОФТ ů 1,4 addition H00 Aldol condensation e ☺ .. . Aldol cond" p Birhen NaoH THE / I add? Brandy CHPPh3 . NGH THE Wittig Reaction NaH + K M9 By Br THE cydisation 86 THE Griganald Reaction as pron Base Ada D NaH THE 2) HOB 1,4 addition again 7,4 addition firs desired product.