Page 309 - Advanced Organic Chemistry Part B - Reactions & Synthesis

(c) O O 281
O O
PROBLEMS

OCH Ph
OCH Ph CH 2 2
HO CH 2 2 TBDMSO
(d )
O O O O
S
CH 3 CH CH O CH 3 CH 2
2
S
(e) CH 3 CH 3 CH 3 CH 3
O O O O
CH 3
CH OCOCH CH CH 3 HOCH 2 CH CH 3
2
3
2
2
CH 3
(f) CH 3 CH 3 CH
O O O 3
O O
CH CH O CH CH
CH 3 CH CH CH 2 2 3 2 3
2
2
3.7. Suggest reagents and approximate reaction conditions that would effect the
following conversions. Note any special features of the reactant that should be
taken into account in choosing a reagent system.
(a) CH O CH 3 O
3
CH O CH CH CH CH OH CH O CH CH CH CH I
2
2
2
2
3
2
2
2
2
3
CH O CH O
3
3
(b) CH(CH 3 2 CH(CH )
)
3 2
(CH ) CH CO H (CH ) CH CO CH CH CH 2
3 2
2
2
2
3 2
CH(CH ) CH(CH )
3 2
3 2
(c) O CH 3 O CH 3
H CH H CH
O 3 O 3
2
CH 2 OH CH CN
(d) CH OH CH SH
2
2
CH OH CH SH
2
2
(e) O CH CH CH CH OH O CH CH CH CH OH
2
2
2
2
2
2
2
2
(CH ) COCNCHCO H (CH ) COCNCHCNHOCH C H
3 3
2
2 6 5
3 3
H H
O