1

Conversion 10
Q.1 R is C3epim or of D-Altrose

(i) Br/H2O

(1) 
HCN/ NaCN
(P)  (Q) 
(i) SnCl2 /HCl
(ii) H 2 O
(R) (ii) dil HNO3
(iii) LiAlH 4 , Et 2 O
(S) 
(i) V2 O5 ,500C
(ii) H 2 / Ni
(T)
(iv) Red P/HI
(v) Al2 O3 Cr2 O3 / 

(i) [Ag( NH3 ) ]OH (i) H  (slight )


(2) (P) 
(i) DIBAL
(ii) H2 O
 (U) 
(ii) H
(iii) SOCl2
(Y)  
(ii) MeOH (1eq.)/HCl
(iii) HIO4
 Organic products
(iv) DIBAL then H2 O (iv) H3O

(i) Br2 /hv

(ii) NaOH
(iii) NaH
(i) HNO3 /H 2SO 4 (i) Br 2 /H 2 O (iv) EtI
(ii) Zn / 
(3) (S) 
(ii)Sn /HCl
(iii) NaOH
(V) 
(iii) Mg(excess)
(W) 
(X) (v) Hot HI
(vi) NaOI
(iv) HNO2 (iv) H 2 O (vii) LiAlH4 then PCC
(v) H 2 O (v) O / Zn
(vi) Zn  Hg/HCl

(i) Me2SO4 ,NaOH (i) CH3Mg Br

(4) (V) 
(ii) T, AlCl3
(iii) Zn  Hg/HCl
 
(ii) H 2 O
(iii) H 2SO 4 ,
(Z)
(iv) SOCl2 (iv) Pd/C
(v) AlCl3 (v) HNO3 /H 2SO4

(i) Na /Liq.NH 3
(ii) m  CPBA(1eq.)
(5) (S) (iii) HIO4
(a) 
(i) O 3 / H 2 O
(ii) B2 H 6 /THF
(b)
(iii) PCC
(iv) N2 H 4

(6) 2(S) X

H2SO
(d)[Find all possible monobromo derivatives]

(i) CH3  I(2eq.)

(7) (X) 
(i) (CH2SH) /HCl
(ii) BuLi(2eq.)
 
(ii) HgCl2 /H2O
 
conc.
H2SO4
(c) [x gm]
[3 gm] [75%]

(i) O3 / H2O
(8) (c) 
(ii) NaOI
(iii) H 2 , Pd/ 
(e) [x gm]
[12 gm] (iv) (X),H [10%]

(i) CO2 / NaOH

(ii) H  (vii) H3O 
(iii) Ac2O/py (viii) H, ∆
(9) (V) 
(iv) LAH
(g) 
(ix) CH MgBr
(h) 3
(v) HCl/ZnCl2 (x) NH4Cl
(vi) NaCN (xi) Conc. H2SO4
 2

O O H3O+
P + Q + R
2.
O

Tollen 's NaHSO3 NaOBr

P 
Q 
R 

(i) SOCl2
(i) DIBAL, –78°C (ii) NH3 (i) HCN/KCN
(ii) H2O (iii) PCl5 (ii) H3O+[Natural form]
(a) P (iii)  S
(iii) Cl2/NaOH (iv) SnCl2/HCl

(i) R, NaOH,  (i) NaBH4, MeOH

(ii) CrO3, H2SO4 (ii) P, H+
(b) Q (iii) SOCl2 (excess)
T
[excess] (iv) H2/Pd, BaSO4

(i) K2Cr2O7,  (i) Conc. H2SO4 [xgm.]

(ii) EtOH, H+ (ii) O3/H2O
(c) R (iii) CH3CH2ONa,  (iii) NaOI
U [100% yield in each reaction]
[2.2gm] (iv) H3O+,  (iv) H+

100% xgm
5.2 gm
3. CaC2 H2O
(a) Red hot
(b) Br2
(c) Mg
(d) CO2 then H3O+
(e) KMnO4
(f)
Fetube Fe Et2O 
(70%) C8H10

NaNH2, BrCH2CCH/AlCl3
CH3–I (80%)

50% (i) BH3–THF Ag(NH3)2+ (i) SOCl2 (i) N2H4

(y) NaNH2 then
(g) (h) (ii) H2O2/NaOH
(i) then H+
(j) (ii) AlCl3
(k) (ii) NaOH, 
(l)
CH–I
(i) NaBH4
H3O+ (100%) Hg2+/H2SO4 70% (ii) H2SO4, 

(i) H2/Pd Fehling O3 Br2

(z) (r) (p) (o) (h) (m) (q)
(ii) Conc. H2SO4 Solution Zn/H2O MeOH

(40%) Conc. H2SO4 NaOH,  (60%)

NaOI SOCl2 Anisole N2H4 (i) H+

(A) zgm (s) (t) (u) (v) (w) (x)
+
then H (100%) AlCl3 NaOH,  (ii) HNO3/H2SO4
ygm