Interactions | Reactions | Processes


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Classified as: Functional Group Interconvertion



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Functional Group Interconvertion (FGI) is a concept associated with "RetroSynthetic Analysis", RSA, a rational approach to the designing synthetic routes to large organic structures, usually of pharmaceutical interest. The oxidation of a secondary alcohol to a ketone is an FGI.
  +  
H2O
  +  
H+(aq)
        
RCHO
  +  
2
R–OH

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(CH3CO)2CO
  +  
2
[OH]–
        
2
[CH3COO]–
  +  
H2O

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(CH3CO)2CO
  +  
2
R–OH
  +  
        
CH3COOR
  +  
CH3COOH

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(CH3CO)2CO
  +  
NH3
        
CH3CONH2
  +  
CH3COOH

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(CH3CO)2CO
  +  
LiAlH4
  +  
8
[H]
  +  
        
2
CH3CH2OH
  +  
H2O

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RCOCl
  +  
H2O
        
RCOOH
  +  
HCl

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RCOCl
  +  
R–OH
  +  
        
  +  

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RCOCl
  +  
2
NH3
        
  +  
NH4Cl

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RCOCl
  +  
LiAlH4
  +  
        
RCH2OH

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RCOCl
  +  
Li[Al(OtBu)3H]
1.0M in THF
  +  
        
RCHO

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RCOCl
  +  
H2
  +  
Pd
on BaSO4
        
RCHO
  +  
HCl

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RCH2OH
  +  
        
RCHO

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RCH2OH
  +  
CrO3
        
RCOOH

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  +  
        

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RCOOH
  +  
R–OH
        
  +  
H2O

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  +  
H2SO4
        
CH3–CH=CH2
  +  
H2O
  +  
H2SO4

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R–I
  +  
RO–
        
  +  
NaI

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(CH3)3COH
  +  
HCl(conc)
        
  +  
H2O

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(CH3)3COH
  +  
HBr
        
(CH3)3CBr
  +  
H2O

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(CH3)3COH
  +  
HI
        
(CH3)3CI
  +  
H2O

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R–OH
  +  
SOCl2
        
RCl

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R–OH
  +  
PBr3
        
RBr

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RCHO
  +  
CrO3
        
RCOOH

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RCHO
  +  
NaBH4
        
RCH2OH

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RCHO
  +  
HCN
        

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RCHO
  +  
H2N–NH2
  +  
OH–(aq)
        
R–CH3
  +  
N2

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RCHO
  +  
Zn(Hg)
  +  
H+(aq)
        
R–CH3
  +  
Zn2+

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RCHO
  +  
2
R–OH
  +  
        
  +  
2
H2O

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RCHO
  +  
  +  
        
  +  
2
H2O

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RCHO
  +  
  +  
        
  +  
2
H2O

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  +  
H2
  +  
Ni/H2
Raney Nickel
        
R–CH3

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RCHO
  +  
        

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RCHO
  +  
R–NH2
        
  +  
H2O

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RCH2CHO
  +  
Br2
  +  
CH3COOH
        
  +  
HBr

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  +  
[OH]–
        
RCOO–
  +  
NH3

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  +  
LiAlH4
  +  
        
RCH2NH2

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  +  
SOCl2
        
R–CN
  +  
HCl
  +  
SO2

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CH4
  +  
Cl2
  +  
hν
        
CH3Cl
  +  
HCl

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  +  
HCl
        

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  +  
HBr
        

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  +  
HI
        

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  +  
Cl2
        

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  +  
Br2
        

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  +  
H2
  +  
Pd
on C
        
R–CH3

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  +  
        
  +  

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R–C≡C–R
  +  
HCl
        

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  +  
HCl
        

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R–C≡C–R
  +  
Cl2
        

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  +  
Cl2
        

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R–C≡C–H
  +  
HgSO4
  +  
H+(aq)
        

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R–C≡C–H
  +  
  +  
HOOH
  +  
NaOH
        
RCH2CHO

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2
  +  
BF3←THF
in THF
        
  +  

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R–C≡C–R
  +  
H2
  +  
Pd + Pb
on CaCO3
Lindlar Cat.
        

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R–C≡C–R
  +  
Li
  +  
NH3
        

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  +  
R–NH2
        
  +  
R–OH

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R–NH2
  +  
10
CH3I
  +  
Ag2O
        
  +  
(CH3)3N

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  +  
HNO2
  +  
H+
  +  
H2O
        
  +  
2
H2O

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  +  
KMnO4
        

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  +  
2
H2
  +  
Pd
on C
        
  +  
H2O

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  +  
Cl+
        
  +  
H+

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  +  
Cl+ / [AlCl4]–
        
  +  
H+
  +  
[AlCl4]–

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  +  
Br+
        
  +  
H+

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  +  
Br+ [FeBr4]–
        
  +  
H+
  +  
[FeBr4]–

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  +  
I2
  +  
CuCl2
        

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  +  
[NO2]+
        
  +  
H+

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  +  
HNO3
  +  
H2SO4
        
  +  
H2O

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  +  
H2S2O7
        
  +  
H2SO4

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  +  
H2S2O7
  +  
H2O
        
  +  
H2SO4

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  +  
HSO3Cl
        
  +  
H2O

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  +  
KMnO4
  +  
OH–(aq)
        
  +  
RCOOH

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RCl
  +  
AlCl3
        
R+ [AlCl4]–

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RCOCl
  +  
AlCl3
        

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  +  
CuCl
        
  +  
N2
  +  
Cu+

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  +  
CuBr
        
  +  
N2
  +  
Cu+

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  +  
NaI
        
  +  
N2
  +  
Na+

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  +  
H2O
        
  +  
N2
  +  
H+

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  +  
H3PO2
  +  
[H]
        
  +  
N2

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  +  
NaOH
        
  +  
Na+
  +  
[HSO3]–

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RCOOH
  +  
Base–
Proton abstractor
        
RCOO–
  +  
Base-H
Protonated base

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RCOOH
  +  
LiAlH4
        
RCH2OH

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2
RCOOH
  +  
B2H6
        
2
RCH2OH

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RCOOH
  +  
SOCl2
        
RCOCl
  +  
SO2
  +  
HCl

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RCOCl
  +  
RCOO–
        
(RCOO)2O
  +  
Cl–

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RCOO–
  +  
RCl
        
  +  
Cl–

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RCOOH
  +  
CH2N2
        
  +  
N2

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  +  
HCl
        

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  +  
H+(aq)
        

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  +  
[OH]–
        
RCOO–
  +  
R–OH

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  +  
NH3
        
  +  
R–OH

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  +  
LiAlH4
        
RCH2OH
  +  
R–OH

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  +  
        
RCHO
  +  
R–OH

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RCl
  +  
Mg
        
RMgCl

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RBr
  +  
Mg
        
RMgBr

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CH3I
  +  
Mg
        
CH3MgI

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RMgCl
  +  
H2O
        
R–H
  +  
Mg2+
  +  
[OH]–

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CH3MgI
  +  
H2O
        
CH4
  +  
Mg2+
  +  
[OH]–
  +  
I–

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  +  
Base–
Proton abstractor
        
  +  
Cl–

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  +  
Base–
Proton abstractor
        
  +  
Br–

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  +  
Base–
Proton abstractor
        
  +  
HI

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  +  
NaOH
        

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  +  
NaBH4
        
R2CHOH

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  +  
H2N–NH2
  +  
OH–(aq)
        
  +  
N2

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  +  
HCN
        

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  +  
  +  
        
  +  
2
H2O

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  +  
        
  +  
H2O

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  +  
H2
  +  
Ni/H2
Raney Nickel
        

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  +  
        
  +  
(C6H5)3P=O

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  +  
R–NH2
        
  +  
H2O

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  +  
NH3
        
  +  
H2O

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  +  
Br2
  +  
CH3COOH
        
  +  
HBr

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  +  
Zn(Hg)
  +  
H+(aq)
        

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R–CN
  +  
H+(aq)
        
RCOOH
  +  
[NH4]+

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R–CN
  +  
LiAlH4
  +  
4
[H]
        
RCH2NH2

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R–CN
  +  
        
RCHO

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  +  
2
Fe
  +  
6
H+
        
  +  
2
H2O
  +  
2
Fe3+

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  +  
3
Sn
  +  
6
H+
        
  +  
3
Sn2+
  +  
2
H2O

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RBr
  +  
Li
        
RLi
  +  
LiBr

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RLi
  +  
CuBr
        
R2CuLi
  +  
LiBr

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  +  
[OH]–
        
  +  
H2O

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RCOCl
  +  
        
  +  
Cl–

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  +  
RBr
        
  +  
Br–

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  +  
(KSO3)2NO
        

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  +  
NaBH4
  +  
2
[H]
        

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R2S
  +  
R–I
        
[R3S]+
  +  
I–

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  +  
CH3I
        

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R2S
  +  
        
  +  

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[R–S]–
  +  
R–I
        
R2S
  +  
I–

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2
[R–S]–
  +  
Br2
        
R–S–S–R
  +  
2
Br–

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[R2OH]+
  +  
Br–
        
RBr
  +  
R–OH

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  +  
NaH
  +  
        
  +  
H2
  +  
Na+

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R–CH2–Br
  +  
        
[(C6H5)3P–CH2R]+
  +  
Br–

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[(C6H5)3P–CH2R]+
  +  
NaH
        
  +  
H2

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RBr
  +  
(CH3CH2O)3P
        
  +  
CH3CH2Br

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R–CH2–Br
  +  
(CH3CH2O)3P
        
  +  
CH3CH2Br

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  +  
(CH3CH2O)3P
        
  +  
CH3CH2Br

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R–NO2
  +  
2
(CH3CH2O)3P
        
R–N
  +  
2
(CH3CH2O)3P=O

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  +  
[OH]–
        

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  +  
H2S
  +  
[OH]–
        

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  +  
NH3
        

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  +  
LiAlH4
  +  
2
[H]
        
CH3CH2OH

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  +  
[OH]–
        
  +  
H2O

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  +  
SO2
        

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  +  
Br2
        
(CH3)3CBr
  +  
HBr

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  +  
Cl2
        
  +  
  +  
HCl

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  +  
Cl2
        
  +  
HCl

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  +  
3
H2
  +  
Rh
on Carbon
        

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RCHO
  +  
R–OH
  +  
        
  +  
H2O

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  +  
R–OH
  +  
        
  +  
H2O

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  +  
2
R–OH
  +  
        
  +  
2
H2O

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  +  
H2O
        

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  +  
H2O
  +  
H+(aq)
        
  +  
CH3COOH

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RCOOH
  +  
SF4
        
R–CF3
  +  
SO2

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R–OH
  +  
SF4
        
R–F
  +  
SO2

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CH4
  +  
2
Cl2
  +  
hν
        
CH2Cl2
  +  
2
HCl

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CH4
  +  
3
Cl2
  +  
hν
        
CHCl3
  +  
3
HCl

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CH4
  +  
4
Cl2
  +  
hν
        
CCl4
  +  
4
HCl

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  +  
2
[Ag(NH3)2]+
  +  
3
NaOH(aq)
        
  +  
2
Ag
  +  
4
NH3
  +  
2
H2O
  +  
3
Na+

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CH3CHO
  +  
2
[Ag(NH3)2]+
  +  
3
NaOH(aq)
        
[CH3COO]–
  +  
2
Ag
  +  
4
NH3
  +  
2
H2O
  +  
3
Na+

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  +  
[OH]–
        
  +  
HBr

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RCOOH
  +  
2
LiCH3
        

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© Mark R. Leach 1999 –

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please contact Mark R. Leach, the author, using mark@meta-synthesis.com