Page 801 - Advanced Organic Chemistry Part B - Reactions & Synthesis

O 777
O
CH 3
OCCH
CH 3 2 PROBLEMS
(a) Br O
and CH 3
CH O H
3
CH O
3
(b) O CH 2 CH 3
O CH C(CH ) CH 3
2 5
and HC C(CH ) CH 3
2 5
(c) CH 3 CH 2 CH 3 CH CH CH C CSi(CH )
3
2
3 3
2
)
O and BrCH C CSi(CH 3 3 O
2
CH 3 CH 3
(d) O O
and HC CH, C H I CH CH 3
2 5
2
H H
NCCH CH
(e) CH 3 CH CHCN H C CH
F Br CH 3 3 3
and F
Br
CH 3 CH 3

8.9. A number of syntheses of medium- and large-ring compounds that involve
transition metal reagents or catalysts have been described. Suggest an
organometallic reagent or catalyst that could bring about each of the following
transformations.
(a) CH 3 CH 3
CH Br
2
BrCH 2 CH 3
CH 3 CH 3 CH 3
CH 3 CH 3
(b) O CH 3
CO CH 3
2
2
CH 3 CO CH 2 O
CH CH 3
CH 3 3 CO CH 3
2
CH 3 CH 3
O
(c)
CO
(CH )
O CH CH 2 2 10
) C
(PhSO 2 2 (CH )
2 10
(PhSO ) CH(CH ) CO (CH ) H
2 10
2
2 10
2 2
CH 2 C
C CH
H OH