Page 493 - Advanced Organic Chemistry Part B - Reactions & Synthesis

466 CH 3 CH 3 CH 3

CHAPTER 5
Reduction of O O O
Carbon-Carbon Multiple H H
Bonds, Carbonyl CH 3 CH 3 CH 3
Groups, and Other
Functional Groups
5.8. The fruit of a shrub that grows in Sierra Leone is very toxic and has been
used as a rat poison. The toxic principal has been identified as Z-18-fluoro-
9-octadecenoic acid. Suggest a synthesis from 8-fluorooctanol, 1-chloro-7-
iodoheptane, acetylene, and any other necessary organic or inorganic reagents.
5.9. Each of the following compounds contains more than one potentially reducible
group. Indicate a reducing agent that will be suitable for effecting the desired
reduction. Explain the basis for the expected selectivity.
(a) H CO CH 3 H CO CH 3 (b) O H OH H
2
2
O O O O
O O
O H O H O O
H O H O
CH 2 CH
CH CH 3
3 3
O OCH CH O OCH
CH 3 3 3 3
OCH OCH
3 3
(c) HO C HOCH 2 (d) CH CH C CCH C CCH OH
2 O CH 2 CO 2 C 2 H 5 O CH 2 CO 2 C 2 H 5 3 2 2 2
H
CH CH C CCH
O O O O 3 2 2 CH OH
2
CH CH CH 3 CH 3 H
3 3
(e) CH O CH 2 CHCH CO CH CH O
3 2 2 3
3
CH CH CHCO OTMS CH CH CHCO CH CH CCH CHCH CO CH
3 2 2 3 2 2 2 2 2 2 2 3
H H CH
CH 3 3
OTMS
(f) O O
CH (CH ) C(CH ) CO H CH (CH ) C(CH ) CH O
3 2 3 2 4 2 3 2 3 2 4
(g) OCH Ph OCH Ph
H 2 H 2
CH 3 H CH 3
HOH C OH H H C OH H
2
3
(h) CH 3 O O CH O
3
CH O
Ph NOCH3 Ph
CH 3 CH 3 CH 3
(i) CH 3 CH
3
O CH O O CH
3 3
O O
O H HC H
CH 3 CH 3
O OSiR HO OSiR
3 3