Try this conversion after complete revision of reaction mechanism.

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conc.HI

59 61 HCN/OH
1
H/H2O
2
(Chemistry Simplified)
(i)O 3 (i)NaCN
CH3I C2H5I 3
68 69 (ii)HCl
(ii)H 2O
(i)O 3 NaHSO 3
71 55 56 57 58 60 64 65 66 4
70
(ii)Zn/H 2O 19
2CH3OH
HBr 5 16
72 SOCl2
H2O2 PCl3 NaOBr H
PCl5 pyridine Na NaH K2Cr2O7 /H (CH3CO)2O
CH3NH2 LiAlH4
73 HBr 6 7 conc.HI
pH 4-5 ether
79 NH2NH2 18 39
H/H2O 8 15
74 O pH 4-5
N2H4 /OH (i)Red P + Br2
H2 /Pd/CaCO3 (i)BH3 /THF conc.H2SO4 H2 /Ni C2H5ONa H2 Ni
75 67 54 H3C CH3 9 (ii)H 2O
(ii)H2O2 /OH C2H5ONa H/H2O Ca(OH)2
Zn-Hg/HCl Cl 2 HBr NaI KCN
CH3I 3NaNH2 Br2 /CCl4 10 11 12 13 14 17 20 40
78 77 76 NaOI h C2H5OH H2 O 2 acetone DMSO

Br2 /H2O (i)B2H6 H CHCl3

81 85 86 41
88 87
Na/Liq.NH 3 49
(ii) H/H2 O (yellow ppt.)
(i)Hg(OAc)2,H2O NaOH + CaO NH3 PCl3 SOCl2 CH3OH H NaOH +
NaOH OH
82 42 CaO
(ii)NaBH 4 Kolbe's Na/Liq. NH3
80 90 89
electrolysis 91
Baeyer's reagent LiAlH 4
83 43 V2 O 5 21 25 35 37 38
48 50
Br2 h 450 C
(i)m-CPBA NaBH4 KOBr NH3 CH3ONa
84 44 Red hot
Br2 Na
(ii)H/H2O 94 93 92 Fe tube 500 C
h dry ether 22
I2 + NaOH 26 36
KCN Ag
Mg ether 45 46 47
P2O 5 OH/H2 O (yellow ppt.) CHCl3 KOH NaOH Br2
96 95 dil.H2SO4 +
97 (partial hydrolysis)
100 HgSO4
(i)DIBAL-H 23 27
98 (ii)H 2O OH 52
51
O LiAlH4 HNO2
SnCl 2 + HCl
99 H2C CH3 HCHO CH3CN SeO2
(ii)H/H2O H/H2O C2H5OH PhNH2
(ii) H/H2O (ii)H/H2O (ii)H/H2O 24 28
53
101 102 103 104 105 106

PCC Cu Red P SOCl2

HBr H
573K HI

29 30 31 32 33 34
Try this conversion after complete revision of reaction mechanism.
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44

NaNO2 + HCl
(Chemistry Simplified)
dil.H2SO4
39 24
Electrolytic
H3PO2 /H2O 43 reduction conc.H2SO4
59 40 C2H5I Zn dust
V2 O5 5
CH3CH2OH 25 Na
60 57 58 LiAlH4 Zn 300 C 23
38 Na 2Cr2O7
NH4Cl 6
NaNO 2,Cu HBF 4 CH3COCl
61 oleum NaOH
62 PhOH PhNH2 42 20 21 22 dil. HNO 3
H2 /Pd 350 C 7
Ph 10-11 Ph 5-6
HBF 4 37 (ii) H
63
Br2
CHCl3 + KOH 8
CS2
KI
64 Sn HNO3 + H2SO4 HNO3 + H2SO4 NaNO2 + HCl Br2
NaNO 2 + HCl Sn + H2 O
56 41 36 1 2 3 4 9
Cu/HCl 273-278K HCl HCl 273-278K H2 O
65
conc.H2SO4
10
Cu/HBr 25 C
66
Cl2 / AlCl3 NaOH NaOH CH3I conc.H2SO4
26 27 28 29 11
Cu2Cl2 /HCl 623K,300atm 100 C
67 Br2 CS2 Br2 H2O Ac2O Pyridine HNO 3 +
CH3COCl Pyridine (ii) H CHCl3 + NaOH
H2SO4 12
Cl conc.HI
Cu2Br2 /HBr O2 H/H2O (ii) H
68 32 33 34 35
45 46 47 50 (51 ) 53 AlCl3 CCl4 + NaOH
13
+ 30 31 (ii) H
CuCN/HCN
69 Br2 CH3CO2H HNO 3
51 (47 ) CO2 + NaOH
H2SO4 14
125 C, 5atm
+
H/H2O (ii) H
48 52 (2 ) 54

70
H/H2O H/H2O
Ac2O Br2 H2O CH3OH H PhOH H NaOH +
CaO
49 55

NaOH + Cl2 /AlCl 3

CH3OH H SOCl2 PCl3 NH3 88 15 16 17 18 19
CaO
Cl2 /AlCl 3
excess 89
71 72 74 77 87
3Cl2 /UV
P2O 5 90
H2 /Pd/BaSO 4 NH3 NaOH + Br2 500K
Br2 Mg/ether CO2
91 92 93
Fe (ii) H
73 75 78 79
I2 Na
95 94
HNO 3 dry ether
KOBr (CH3CO)2O Zn-Hg/HCl
96 97
DIBAL-H H2 /Ni AlCl3
(ii)H2 O CO + HCl
76 98
AlCl 3
80 83 HCN + HCl/AlCl 3
99 CrO2Cl2 /CS2
(ii) H/H2O 101
50%KOH HNO 2 (ii) H/H2O
CH3Cl CrO 3 + Ac2O
100
AlCl 3 102
(ii) H/H2O
81 82 84
KMnO 4 /H
103
PCl3 NaCN
85 86
DMSO