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OH
CH2N2
1 eqv. A, A is :
HO
NO 2 OH
OCH3 OH
(A) (B)
HO HO CH3
NO2 OH NO 2 OH
OH OH
(C) (D)
H3CO HO
NO2 OH NO 2 O CH3
1. C
CH3
2. OH O C
HCl
X
CH3
[X] is:
CH3 CH3
(A (B HO O C CH
HO C CH3
) ) H
OH
CH3 CH3
(C HO C C CH (D HO C OH
) O OH ) CH3
2. D
2. H3C H3C H3C
C O H C O H C O H
H3C H3C H3C
CH3 CH3
H3C C OH H3C C O H
H
+
O O O
H H H
So on
OH
3. O
H
x
The major product (x) is
O
O
(A) (B)
OH OH
(C) (D)
3. C
OH
O
4. HCl
+ P(major)
(A) O (B)
OH
OH OH
(C) (D)
HO OH
4. C
PhSO Cl
NaF / DMSO
2
A
B
NO 2
The compound B will be
OH F
F
(A) (B)
NO2 NO 2
OH F
(C) (D)
F F
NO2 NO2
5. B
5. SO 2Ph
OH O F
PhSO Cl
2 NaF / DMSO
NO 2 NO 2 NO 2
(A) (B)
F– is very reactive unsolvated which can displace PhSCO3 which being a good leaving
group in presence of strong withdrawing group —NO2.
OH NH2
CH3
The product ‘A’ is:
CH3 CH3
6. B
6. CH3
OH NH2
HO N N
CH3
CH3
CH3
N2 1,2 shift
CH3O
C CH H3C
CH3 C HC OCH3
HO OH
CH3
H
H3C C HC OCH3
O