Conversion 18 1

62 63

[Link]

59 61 HCN/OH H/H2O
1 2

(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 SOCl H
H2O2 PCl3 PCl5 pyridine2 Na NaH NaOBr K2Cr2O7 /H (CH3CO)2O
CH3NH2 LiAlH4
73 HBr 6 7 [Link]
pH 4-5 ether
79 NH2NH2 18 39
H/H2O 8 15
74 O pH 4-5
H2 /Ni N2H4 /OH (i)Red P + Br2
H2 /Pd/CaCO3 (i)BH3 /THF conc.H2SO4 54 9 C2H5ONa H2 Ni
75 67 H3C CH3 (ii)H 2O
(ii)H2O2 /OH Cl 2 C2H5ONa H/H2O Ca(OH)2
Zn-Hg/HCl HBr NaI KCN 40
CH3I 3NaNH2 Br2 /CCl4 10 11 12 13 14 17 20
78 77 76 NaOI h C2H5OH H2 O 2 acetone DMSO

Br2 /H2O (i)B2H6 H CHCl3

81 85 86 41
88 87
Na/[Link] 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 36
I2 + NaOH Ag 26
KCN
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