SOME IMPORTANT TIPS FOR ORGANIC INTERCONVERSIONS
ALIPHATIC COMPOUNDS
TO CHANGE INTO REAGENT AND REACTION CONDITIONS
--H --Cl Alkyl Chloride Cl2 / sunlight
Alkane
--H --Br Alkyl Bromide Br2 / sunlight
Alkane
Alkene >CH—CH< Alkane Ni/H2 , Pt/H2
˃C==C<
Alkene --C—C— 1,2-Dibromoalkane Br2/CCl4
>C==C< Br Br
Alkene --C—C— Bromo alkane HBr
>C==C< H Br
Alkene --C—C— Alcohol Conc. H2SO4 /warm water
>C==C< H OH
--Br,--Cl,--I --OH Alcohol Aq KOH/NaOH/AgOH
Alkyl halide
--CN Nitrile Alc. KCN
--NH2 Amine NH3
--OCOCH3 Ester CH3COOAg
--MgBr Grignard’s reagent Mg/Dry ether
---COOH Carboxylic acid (i)KCN (ii) H3O+
--OH --Cl Alkyl Chloride PCl5, SOCl2 , HCl/anhyd ZnCl2
Alcohol
--Br Alkyl Bromide PBr3, HBr(aq), NaBr/H2SO4
--I Alkyl Iodide Red P/I2
--ONa Sodium alkoxide Na
--OCOR Ester RCOOH/H2SO4
>C==C< Alkene Conc. H2SO4 /443K
--CH2OH --CHO Aldehyde Cu/573 K
10 alcohol K2Cr2O7/H+
CHOH >C=O Ketone Cu/573 K
20 alcohol K2Cr2O7/H+
--CHO --COOH Carboxylic acid K2Cr2O7/H+
Aldehyde KMnO4/H+
--CH2OH Alcohol Na/Hg + water
Ni/H2 or LiAlH4
--CH(OH)CN Adduct HCN
0
>C=O ---CHOH 2 alcohol Na/Hg + water
Ketone Ni/H2
C (OH)CN Adduct HCN
--COOH --COONa Sodium salt of acid NaOH(aq), Na2CO3, NaHCO3
Carboxylic acid
--COOR Ester ROH/ H2SO4
--COCl Acid chloride PCl5, SOCl2
0
--CH2OH 1 alcohol LiAlH4
--CONH2 Amide (i)NH3 (ii) heat
--COCl --COOH Carboxylic acid H2O
Acid chloride
--COOAr Ester ArOH
--COOCO-- Acid anhydride RCOONa
--CH2OH 10 alcohol LiAlH4
--COOR --COOH Carboxylic acid H3O+
Ester
--COONa Sodium salt NaOH/H2O
--CH2OH 10 alcohol LiAlH4
AROMATIC COMPOUNDS
TO CHANGE INTO REAGENT AND REACTION CONDITIONS
C6H6 --Cl Chloro benzene Cl2/FeCl3 or AlCl3
Benzene
--Br Bromobenzene Br2/FeBr3
--NO2 Nitrobenzene Conc. HNO3 + conc. H2SO4
--R Arene RCl/anhyd AlCl3
--SO3H Sulphonic acid Conc. /fuming H2SO4
C6H5Br --MgBr Grignard reagent Mg/ether
Bromobenzene
C6H5MgBr --OH Phenol (i)O2 (ii) acid
Phenylmagnesiumbromide
--CH2OH Benzyl alcohol (i)HCHO (ii)H3O+
--COOH Carboxylic acid (i)CO2 (ii) H3O+
C6H5OH --ONa Sodium NaOH/623 K
Phenol phenoxide
--OCOR Ester RCOCl, (RCO)2O
--OCOAr Phenyl ester ArCOCl/NaOH
C6H5CN --CONH2 Amide H3O+
Phenyl Nitrile
--COOH Carboxylic acid H3O+
--CH2NH2 Benzylamine Reduction
C6H5N2Cl --OH Phenol H2O/Heat
Benzenediazoniumchloride
--Cl Chlorobenzene CuCl2, Cu/HCl
--Br Bromobenzene CuBr2, Cu/HBr
--I Iodobenzene KI/heat
--F Fluorobenzene HBF4
--CN Cyanobenzene CuCN
--H Benzene H3PO2
SOME IMPORTANT REAGENTS AND THEIR USE IN INTERCONVERSIONS
GRIGNARD’S REAGENT
(1) With aldehydes and ketones
>C==O + RMgX ---- >C—OMgX --------- >C—OH + Mg(OH)X
| H2O |
H2O R R H2O
(i) HCHO + RMgX ----- RCH2OH (ii) RCHO + R’MgX ------- RCH(R’)OH
(iii) RCOR + RMgX ---- R3COH
(2) With CO2 H2O
O==C==O + RMgX ------- RCOOH
(3) With Nitriles H3O+
RC≡ N + RMgX --------- RCOR
(4) With alcohols
ROH + R’MgX ------------ R’H
BENZENEDIAZONIUMCHLORIDE
(1) ArN2Cl + CuCl /HCl --------- ArCl + N2
(2) ArN2Br + CuBr /HBr --------- ArBr + N2
(3) ArN2Cl + CuCN/KCN --------- ArCN + N2
(4) ArN2Cl + KI --------- ArI + N2
(5) ArN2Cl + HBF4 --------- ArF + N2
(6) ArN2Cl + H2O + Boil --------- ArOH + N2
(7) ArN2Cl + H3PO2 + Heat --------- ArH + N2
(8) ArN2Cl + ROH--------- ArH + N2
(9) ArN2Cl + HBF4 + NaNO2 + Cu ------- ArNO2
LITHIUM ALUMINIUM HYDRIDE( LiAlH4)
In dry ether or THF
Substrate reduction product substrate reduction product
(1) RCHO RCH2OH (2) RCN RCHO OR RNH2
(3) RCOR RCHOHR (4) RNO2 RNH2
(5) RCOOH RCH2OH (6) ArNO2 ArNH==NHAr
(7) RCOOR’ RCH2OH + R’OH (8) ArNHCOCH3 ArNHCH2CH3
(9) RCOCl RCH2OH (10) RN=C=O RNHCH3
(11)(RCO)2O 2 RCH2OH (12) RN3 RNH2
JONES REAGENT (CrO3 + CONC. H2SO4)
mild O.A and converts primary alcohol to aldehyde and secondary alcohol to ketone.
PYRIDINIUM CHLORO CHROMATE (PCC ) (C6H5NHCrO3Cl)
Mild O.A and convert primary alcohol to aldehyde
SODIUM BOROHYDRIDE(NaBH4)
Less powerful R.A than LiAlH4 and do not reduce double bond in conjugation while LiAlH4 reduces both
OTHER R.A Sn/HCl, Fe/HCl, Na/Ethanol,Zn/Hg—HCl,Ni,Pt,Pd/H2,Red P/HI,
OTHER O.A Tollen’S reagent, Fehling’s solution
