Page 229 - Advanced Organic Chemistry Part B - Reactions & Synthesis

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(e) 1) CH Li, 2 equiv.
OAc 3 PROBLEMS
H O
C H CH C 13 17 2
6 5
CH 3 2) ZnCl 2
3) n-C H CHO
3 7
O
+ NaOCH CH
–
(f) CH N(CH CH ) I + CH CCH CO CH CH 3 2 3 C H O
10 14
3 2
2
2
2
2
3
2
ethanol, Δ
CH 3
O
(g) O
Na
CH 3 + HCO CH CH 3 ether C H O Na
2
7 9
2
2
O
(h) NaNH 2
CCH + (CH CH O) C O C 11 H 18 O 3
3
2
3
2
toluene
(i)
O O
C H CCH + (CH CH O) PCH CN NaH C 10 9 N
H
2
2
2
3
6 5
3
THF
(j) O
NaOCH 3
CH CH CCH CH CO CH CH 3 C H O 2
2
2
3
2
2
2
6 8
xylene
(k) O O
C CH + (CH ) S CH 2 C 8 12
H O
3
3 2
(l) O – O – H +
CO C H
2 2 5
10 7
+ CH 2 CCH COC H C H NO 3
2 5
N
Li
(m) O
CH 3 1) (CH ) SiCHOCH 3
3 3
H O
CH(OCH ) C 18 28 3
3 2
2) KH
CH 3
CH 2
(n) O NaOH
CH CO 2 O
3
H O
C 12 16 5
+
CH CCH CH 2
3
O
2.2. Indicate reaction conditions or a series of reactions that could effect each of
the following synthetic conversions:
OH
(a) (b)
CO C(CH ) (CH ) CCH CO C(CH )
2 3 3 3 2 2 2 3 3
CH 3
THPO(CH ) CH O THPO(CH ) CH OH
2 3 2 3 2
O O
(c) CHOH Ph CN H CH 3
(d) Ph C O
2
Ph CO 2 C H
2 5
(f) O O O O
(e) O O
CO C H CH OH
2
2 2 5