, linking through
Table 6 4: Nucleophilic Substitution of Alkyl Halides (R–X)
Reagent
Nucleophile
Substitution
Class of main
(Nu–)
product R–Nu
product
NaOH (KOH)
HO–
ROH
Alcohol
H2O
H2O
ROH
Alcohol
NaOR¢
R¢O–
ROR¢
Ether
NaI
I–
R—I
Alkyl iodide
NH3
NH3
RNH2
Primary amine
R¢NH2
R¢NH2
RNHR¢
Sec amine
R¢R¢¢NH
R¢R¢¢NH
RNR¢R¢¢
Tert amine
KCN
RCN
Nitrile
(cyanide)
AgCN
Ag-CN:
RNC
Isonitrile
(isocyanide)
KNO2
O=N—O
R—O—N=O
Alkyl nitrite
AgNO2
Ag—Ö—N=O
R—NO2
Nitroalkane
R¢COOAg
R¢COO–
R¢COOR
Ester
LiAlH4
H
RH
Hydrocarbon
R¢– M+
R¢–
RR¢
Alkane
Rationalised 2023-24
171 Haloalkanes and Haloarenes
carbon atom resulting in alkyl cyanides and through nitrogen atom
leading to isocyanides