(3939) Sheet Structural Identification and Poc Theory H

Structure Identification & POC
1. (Hydrogen Deficiency Index)
:  HDI
2H HDI
(DU) (DBE)
–2H –2H
H3C – H2C – CH3     CH3–CCH CH2=C=CH2
(DU  0)
(DU = 1) (DU = 2)
( 2n  2) – ( H  X –N )
(D.U.) =
2
n=
: +
= DU
= DU
= DU
(2  2  2) – 4
. (i) CH2 = CH2 DU = = 2/2 = 1 (ii) DU = 2
2
(iii) DU = 4 (iv) DU = 7
(2n  2) – 6 14 – 6 14 – (5  1)
(v) C6H6O DU = = =4 (vi) C6H5Cl D.U. = =4
2 2 2
2.
(Cl2, Br2, F2, I2)
C–H C–X H-
: H-
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ADVSIP -1
: H-
H-
: H- H
. (i) CH4 CH3Cl + HCl 1–
(ii) + HCl 1–
(iii) 1–
: H
(iv) CH3 – CH2 – CH2 – CH3 2 ( )
(v) CH3–CH2–CH2–CH2–CH3 3 ( )
(vi) 4 ( )
(vii) 5 ( )
3.
Ni/Pt/Pd
–  (C=C, CC)
(i) 
(ii)
(iii) 
(iv)
:  )
:
Ni
(a) R – CH = CH – R + H2 
 R – CH2 – CH2 – R
Ni / Pt / Pd
(b) R – C  C – R + 2H2      R – CH2 – CH2 – R
H2
R – CH  CH – R   R – CH2 – CH2 – R
( )
ADVSIP -2
H / Ni
(c) CH2 = CH – CH2 – CH3 2 CH3 – CH2 – CH2 – CH3
2 H / Ni
(d) 2 
CH – CH
4.
C=C CC
(i)
: (1) O3 ( ) (2) Zn (CH3)2S H2O CH3COOH
(ii)
: (1) O3 ( ) (2) H2O2 H2O
(i)
(ii)
(i)
R–CH=O + + ZnO + H2O
R–CC–H + ZnO + H2O
(ii)
R–COOH + + H2O
R–CC–H R–COOH +
(a) CH2=CH2 CH2=O + CH2=O
(b) CH3–CH2–CH=CH2 CH3–CH2–CH=O + O=CH2
(c) CH2=CH–CH2–CH=CH–CH3 CH2=O + O=CH–CH2–CH=O + O=CH–CH3
(d) 2 OHC–CH2–CHO ( )
(e) O=CH–CH2– –CH2–CH=O + O=CH2
ADVSIP -3
O ( )
3
(f) Zn,H O ( )
2
(g)
5. (POC) :
(A) :
H2
H: H O, N,S, X, Csp H
1
:Z– + Na  + H 
2 2
Na 1 Na 1
. (a) R  NH2 
 R  NHNa  H2  (b) R  SH 
 RSNa  H2 
2 2
Na 1 Na 1
(c) R  COOH 
 R  COONa  H2  (d) PhOH 
 PhONa  H2 
2 2
1 1
(e) R—OH + Na  R— O–Na+ + H  (f) R—SO3H + Na  R—SO3–Na+ + H 
2 2 2 2
1
(g) R—C  CH + Na  R—C  C–Na+ + H  (h) R — CH = CH2 + Na 
2 2
Na 1
(i) R — CH2—O —CH3 + Na  (j) HCl 
 NaCl  H2 
2
(B) :
(i) ( Br2 + H2O, ) :
Br ,H O
R–CH2 –CH3 22

Br ,H O
2 2
R–CH = CH2  
Br2 ,H2O
R–C CR   
ADVSIP -4
(ii) KMnO4
Cold, dil.KMnO
4
R–CH2 –CH3   
Cold, dil.KMnO
4
R–CH = CH2   
Cold, dil.KMnO
4
R–C CR   
(C)

(i) [AgNO3 + NH4OH {Ag(NH3)2}+ OH ] :
AgNO NH OH
3 
4 
R–C  CH   R–C  CAg + NH4NO3
(ii) (Cu2Cl2 + NH4OH) :
Cu Cl NH OH
R–C  CH 22
4
 R – C  CCu  + 2NH4Cl + 2H2O
(D)
(i) HCl + ZnCl2)
* turbidity or Cloudiness
* 1°, 2°, 3°
(a) 1° R–CH2–OH (1°) R–CH2–Cl

30
(b) 2° R2CH –OH (2°) 5
(c) 3° R3C – OH (3°) R3C–Cl

*
(ii)
1°
2°
3°
ADVSIP -5
(iii) :
(1°,2°,3°) [(NH4)2Ce(NO3)6]
(E)
FeCl3 :
OH sp2
3
 – 
6 PhOH + FeCl3   Ph O  Fe  3HCl
 
 6 
( )
*
(F)
2, 4-DNP 2, 4–
2, 4-DNP
(G) :

(a) [AgNO3 + NH4OH {Ag(NH3)2}+ OH ] :
O
AgNO3 NH4OH ||
R–CH = O      R – C – O  + Ag 
HCOOH
(b)
(I) (CuSO4 (II) )
CuSO4 + 2NaOH  Cu(OH)2 + Na2SO4
Cu(OH)2 +  + 2 H2O
(Cu2O)
R – CHO + 2CuO  RCOOH + Cu2O ( ppt)
RCHO + 2Cu2+ +  + + 2H2O
(c) :
(I), (II),
CuSO4 + 2NaOH  Cu(OH)2 + Na2SO4

ADVSIP -6
Cu(OH)2 + 
2 
RCH = O + 2Cu +  + 2Cu  2H2O
(d) :
SO2
(H2SO3 )
*
(H)
: I2 + NaOH NaOI R = H,
(I)
(i) (NaHCO3)
H2CO3 NaHCO3 CO2
HCl + NaHCO3  NaCl + H2CO3
H2O + CO2 
RSO3H + NaHCO3  RSO3Na + H2CO3

H2O + CO2 
: (NO2)
ADVSIP -7
(ii)
(iii)
(iv)
NaOH

RCOOR’ + NaOH + ( )  R COOH + R’ OH ( )
(J) :
(i) NaNO2 + HCl 1º, 2º 3º
1° R–CH2–NH2 R–CH2–OH + N2 
1° : )
2° R – NH – R (N - )
3° : R3N
(ii) (CHCl3 + KOH)

CHCl 3 KOH
1° R–CH2–NH2     R–CH2–N  C + 3KCl + 3H2O
CHCl KOH
Ph – NH2  3   Ph – N  C
* 2° 3°
(iii) 1º
(HgCl2)
HgCl2
(a) R – NH2 + S=C=S  R – NH –  
 R – N = C = S + HgS + 2HCl

 HgCl
2
(b) CH3CH2NH2 + S = C=S      CH3CH2–N = C=S + HgS + 2HCl

(1º )
(c) C6H5NH2
* 2° 3°
ADVSIP -8
(iv) (C6H5SO2Cl) :
1°,2° 3°
1° R–NH2 + PhSO2Cl R–NH–SO2–Ph
2° R2NH + PhSO2Cl R2N–SO2–Ph
3° : R3N PhSO2Cl
(K) :( )
Zn
(a) R–NO2 R–NHOH Ag

Ag
(b) + Zn + NH4Cl  AgNO NH OH

3 
4  
 
(L)
: -
2 ml 1 ml
(M) :
:
6. :
(A) :
(II)

C + 2CuO  2Cu + CO2

2H + CuO  Cu + H2O

CO2 + Ca(OH)2  CaCO3 + H2O

5H2O + CuSO4  CuSO4.5H2O
(B) :
ADVSIP -9
C, N, S X

Na + C + N  NaCN

2Na + S  Na2S

Na + X  NaX

Na + C + N + S  NaSCN
(i) :
(II) H2SO4
FeCl3 HCl
6NaCN + FeSO4  Na4[Fe(CN)6]

Na4[Fe(CN)6] + 4Fe3+ 
xH2O
 Fe4[Fe(CN)6]3. xH2O
( )
(ii)
(a)
Na2S + (CH3COO)2Pb  PbS
(b)
Na2S + Na2[Fe(CN)5 NO]  Na4[Fe(CN)5NOS]

( / )
(c)
FeCl3 N
S
Na + C + N + S  NaSCN
FeCl3 + NaSCN  Fe(SCN)3
(iii) :
: HNO3
AgNO3
NaX + AgNO3  AgX 
ADVSIP - 10
(iv) :
Na3PO4 + 3HNO3  H3PO4 + 3NaNO3
H3PO4 + 12(NH4)2MoO4 + 21 HNO3  (NH4)3PO4. 12 MoO3 + 21 NH4NO3 + 12H2O
ADVSIP - 11

(3939) Sheet Structural Identification and Poc Theory H

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(3939) Sheet Structural Identification and Poc Theory H

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Structure Identification & POC

1. (Hydrogen Deficiency Index)

. (i) CH4 CH3Cl + HCl 1–

(iv) CH3 – CH2 – CH2 – CH3 2 ( )

R–CH=O + + ZnO + H2O

R–CC–H + ZnO + H2O

(a) CH2=CH2 CH2=O + CH2=O

(b) CH3–CH2–CH=CH2 CH3–CH2–CH=O + O=CH2

(c) CH2=CH–CH2–CH=CH–CH3 CH2=O + O=CH–CH2–CH=O + O=CH–CH3

(e) O=CH–CH2– –CH2–CH=O + O=CH2

(ii) (Cu2Cl2 + NH4OH) :

(a) 1° R–CH2–OH (1°) R–CH2–Cl

(b) 2° R2CH –OH (2°) 5

(c) 3° R3C – OH (3°) R3C–Cl

(I) (CuSO4 (II) )

CuSO4 + 2NaOH  Cu(OH)2 + Na2SO4

Cu(OH)2 +  + 2 H2O

R – CHO + 2CuO  RCOOH + Cu2O ( ppt)

RCHO + 2Cu2+ +  + + 2H2O

CuSO4 + 2NaOH  Cu(OH)2 + Na2SO4

RSO3H + NaHCO3  RSO3Na + H2CO3

(ii) (CHCl3 + KOH)

1° R–NH2 + PhSO2Cl R–NH–SO2–Ph

2° R2NH + PhSO2Cl R2N–SO2–Ph

(a) R–NO2 R–NHOH Ag

(b) + Zn + NH4Cl  AgNO NH OH

6NaCN + FeSO4  Na4[Fe(CN)6]

Na2S + (CH3COO)2Pb  PbS

Na2S + Na2[Fe(CN)5 NO]  Na4[Fe(CN)5NOS]

FeCl3 + NaSCN  Fe(SCN)3

NaX + AgNO3  AgX 

Na3PO4 + 3HNO3  H3PO4 + 3NaNO3

H3PO4 + 12(NH4)2MoO4 + 21 HNO3  (NH4)3PO4. 12 MoO3 + 21 NH4NO3 + 12H2O

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