ROADMAP PROBLEM : 1

Conc. H2SO4
A (Solution is dextro rotatory) Black particles (B)
specific rotation = +66°
H2O

Conc. H2SO4 Same

A1 + A2 A1 or A2 Black particles
dextro Laevo observed
rotatory rotatory
(Overall mixture of A1 and A2 is laevorotatory)
+ Black + H2O
CaCO3 CO2 + CaO D E
Particles /

red hot
E F G (Not aromatic)
NaNH2 Fe tube Cl2 / 500 K
(2 eq) (873 K)
H (Aromatic)
I Cl2 + AlCl3
H2(Ni)
(excess) (dark cold)
CH3I high
pressure Cl2 + AlCl3 (anhydrous)
(2 eq) P Se / R
and Na / D.E.
temp. NBS
J RO– / ROH /
Red hot Br2 Alcohol +F
M N O Q
Fe tube h KOH / +H
+

(Mono
K bromo
product)
KMnO4 (excess) HNO3 Fe + HCl NaNO2
(high temp.)
P S T U
+ H2SO4 (Major + Conc. H2SO4
Steam
product)
L (cyclic trianhydride)

(i) N2H4 + OH– Zn / AlCl 3 AcOH / H

+

Z Y X W V
(ii) Br2 / h

NaHCO3 + DMSO

1
 ROADMAP PROBLEM : 2
A + X + Y (where X and Y are constituents of sucrose)

NaOH
Ph–NH–NH2 HIO4 D PhMgBr H
Osazone A B + C F G + H D
H2SO4 1 eq.
I / H2SO4
Red P KCN /
(1) KOH MeMgBr / 1eq
HI / Oil of winter
(2) H K
J
N green
D+C KCN / H3O Dil. HNO3
DDT
Al2O3 (Reduced Lactic acid (1) KOH
Chloral Cr2O3 product) L M
H2SO4 MoO3 / (2) H
Cl2
Q O
FeCl3
Mg MeCN / HCl / ZnCl3 / H3O

R P
O2 / H NaOI / H
Phenol T / H2SO4
NaOH MeCl CrO2Cl2 Tollen's reagent
S Yellow ppt + V O Z G V + Silver mirror
phthalein CaO / AlCl3 Ac2O H
CO2 / NaOH /
Ag / H / KMnO4
/

I Fe tube dil. H2SO4 V

O W J
Ac2O HgSO4

HCl /
U HgCl2
Analgesic
Polymerization
E PVC
 ROADMAP PROBLEM : 3

H2C = CH2
KCN H3O+
(i) Hg(OAc)2 / H2O C Y D E
(ii) NaBH4 PCl5
Br2 / h
P B F
PCC Alc. KOH /
Na / DE
Q NaNH2 (excess) CH3Br (excess)
A G H I
OH /
R PCl3 H2 /PdCaCO3
Quinoline
H2 / Pt
Z
S J
KMnO4 / H + NaBH4
Cold. Alk.
T [X] + YMW = 44 KMnO4
NaOH + CaO EtOH K2Cr2O7 HIO4
(i) O3 N + M L K
H H
+

(ii) H2O / Zn
NaOEt /
Cl2 Alc. KOH
U h V W O
major
 ROADMAP PROBLEM : 3

H2C = CH2
KCN H3O+
(i) Hg(OAc)2 / H2O C Y D E
(ii) NaBH4 PCl5
Br2 / h
P B F
PCC Alc. KOH /
Na / DE
Q NaNH2 (excess) CH3Br (excess)
A G H I
OH /
R PCl3 H2 /PdCaCO3
Quinoline
H2 / Pt
Z
S J
KMnO4 / H + NaBH4
Cold. Alk.
T [X] + YMW = 44 KMnO4
NaOH + CaO EtOH K2Cr2O7 HIO4
(i) O3 N + M L K
H H
+

(ii) H2O / Zn
NaOEt /
Cl2 Alc. KOH
U h V W O
major