1

Conversion 07
Assume 100% yield if not mentioned and also find x & y gm

H O Re d 1. CrO Cl then H O KMnO NaOH

Mg 2 C3 
2 →(P) 
→(Q) 
2 2 2 →(S)  4 →(T)  →(U) [60%]
Hot Fe NaOH,∆ CaO, ∆ 2. Zn-Hg/HCl
[8.4 gm] Tube [50%]

| HCHO,
(1) H2/Pd [y gm] ↓ HCl
[Link] P/Cl2 (2) NaNO2 Sn NaOH CHCl3 AgCN
(b) ←
2. KCN
(a) ←  (Z) 
HCl, 0°C HCl
→(Y) →(X) 
KOH
→(W) ← (V)
[x gm]
|
98%, H 2SO 4
↓
Br NaNO (i) HCHO (i) CO SOCl H /Pd
(c) →
2
NaOH
(d) 
HCl
2 →(e) ←
⊕  (f ) 
⊕ →(g) 
2 2 →(H) 
2
BaSO
→(i)
(ii) H (ii) H 4

Ac2 O / NaOAc, ∆ |
↓
NH KMnO KOH N H H PO H
(P) ←
∆
3
 (O) ←
∆
4 (n) ← (m) ←
∆
2 4 (l) ←
3 4
 (k) ←
2 ( j)
Ni
| KOH/EtOH
↓

H O⊕ NaNO (i) Re d P/Br EtOH (i) EtOΘ

(Q) —→(R) 
3
→(S) 
 HCl
2 →(t) ←
(ii) KOH
2 (u) →(v) →(w)
⊕ +
H (ii) H3O , ∆

| NaBH 4 ,
↓ MeOH
(i) LiAlH CH NH O tBuONa HBr H SO
(D) ←
(ii) H O
4 (C) ←
3
∆
2
(B) ←
3
H O
(A) ←
∆
 (z) ←
CCl
 (y) ←
2
∆
4 (x)
2 2 2 4

??
AgCN HBr (i) O BH Conc. dil. PCC
(E) ←(F) ←
R O
(G) (ii)
H O3 →(H) THF
3 →(I) H
SO

→(J)  
H SO
→(K)  
→(L)
2 2 2 2 2 4 2 4
| Conc.,
↓ H 2SO 4
NaNH 1% HgSO HIO 1% KMnO H (i) NaNH Re d hot
(5) ← 2 (4) 
(2 eq.) H SO
4 →(3) ←
4 (2) ←
0° C
4 (1) ←2
Pd/BaSO
 (O) ← 2 (N) 
(ii) CH I Fe tube
→(M)
2 4 4 3
| CH − I(2 eq.)
↓ 3

Na m −CPBA H O H⊕ NaOI O H
(6) 
liq. NH
→(7) →(8) 
2 →(9) 
→(10) →(11) ←3
H O
 (12) 2
Pd
→(13)
3 2
| Al2 O3 ,
↓ Cr2 O3
N H (i) OsO O (i) NaOEt O Na
(20) ←
2 4  (19) ←
pH 6.0
4  (18) 
(ii) H IO
3
Zn/H O
→(17) ←
(ii) Et − I
(16) ←3
Zn/H O
 (15) ←
Liq. NH
 (14)
5 6 2 2 3

Total products obtained ?