Page 1017 - Advanced Organic Chemistry Part B - Reactions & Synthesis

H 993
(p)
(q)
Pb(OAc) 4
O C 21 H 25 BrO 7 OH PROBLEMS
O 2 CCH 3 I 2 , hν AIBN
CH 2 OH S
H + CH 2 CHCH 2 SnBu 3
O CH 3 Br
CH 3 CO 2 O
CH 3 O CH 2 OCOPh
C 10 H 18 O 3
(r)
+ C 2 H 5 O 2 CN
CH 2 CHCH 2 CH 3 NCO 2 C 2 H 5 C 10 H 18 N 2 O 4
AlCl 3
(s) (CH 3 ) 2 C CHCH 3 + HC CCO 2 CH 3 C 9 H 14 O 2
O CH 3
(t) C
CO 2 C(CH 3 ) 3 (u) CH 3 O
NCH h ν n-Bu 3 SnH C 26 H 48 O 4 Sn
C 20 H 28 N 2 O 5 S O
CO N CH 3 AIBN
CH 2
105°C
O
O S O
CH 3
CH 3
CH 2 OCH 2 Ph
(v) O
Si(CH 3 ) 3 TiCl 4 C 27 H 34 O 3
O
CH 3
1) CH 3 SO 2 Cl,
CH 3 CH 3
(w) (x) CH 3 pyridine
O HO
TiCl 4 C 12 H 20 O
C 11 H 15 NO OH 2) NaH, 65°C
(CH 2 ) 4 N 3
CH 3 CH 2
10.2. Indicate appropriate reagents and reaction conditions or a short reaction sequence
that could be expected to effect the following transformations:
(a) O O H H
CH 2 Ph CH 2 Ph (b) O
N 2
Cl O
CH 3 Cl CH 3
O
(c) (d)
CH 3 CH 3
PhCNHCH 2
NCO 2 CH 3
NCO 2 CH 3
OH OH NCO 2 CH 3
NCO 2 CH 3
(e)
(f)
H CO 2 C 2 H 5 H NHCO 2 CH 2 Ph CH 3 CH 3
CO 2 H O
Ph CO 2 C 2 H 5 Ph CO 2 C 2 H 5
(CH 3 ) 2 CH (CH 3 ) 2 C
(g)
CHCH CHCO 2 H CHCH CHNHCO 2 CH 2 Ph
CH 2 CH 2
CO 2 C 2 H 5
(i) CH 3 CH 3
(h)
CH 3 CH 3
O
OCH 3
CH 3 CH 3 OCH 3