Actually cyanide group is a
hybrid of two contributing structures and therefore can act as a
nucleophile in two different ways [VCºN « :C=NV], i e , 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