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 Similarly nitrite ion also represents an ambident
nucleophile with two different points of linkage [–O— N
i i
=O]