Question

How would I do these two synthesis? Suggest a reasonable sequence of Reagents that could convert 2-cyclohexen-1-one into each compound:

I am struggling with D and H. Sorry if the picture quality isn't great, the site won't allow any better. In H it is a =O and the starting compound has a double bond on the side.

Answer 1

Reagents for transformation

D : 1. H2,Pd-C ; 2. NaBH4 ; 3. Na, PrCl [reduction of alkene to alkane, then reduce ketone to alcohol andprotect with alkyl halide by Williamson's type reaction]

H : (C4H9)2CuLi [coupling with gilman reagent in a 1,4-fashion]