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Structural Identification and Practical Organic Chemistry
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Difficulty 1 of 3
si173
Aniline is treated with
NaNO
X
2
/
HCl
at 273 K to give A, which is warmed with
CuCN
to give B. B is
A
phenyl isocyanide,
C
X
6
H
X
5
NC
B
benzylamine,
C
X
6
H
X
5
CH
X
2
NH
X
2
C
benzonitrile,
C
X
6
H
X
5
CN
D
benzoic acid,
C
X
6
H
X
5
COOH
Answer: C
Diazotisation gives benzenediazonium chloride (A). The Sandmeyer reaction with
CuCN
replaces the diazonium group by
−
CN
to give benzonitrile.
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