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Q.

Which of the following statements are correct?

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a

The resonance stabilization of naphthalene is twice that of benzene

b

The oxidation of one ring of naphthalene to give phthalic acid is easily performed as compound to the oxidation of benzene.

c

The oxidation of 1 – nitronaphthalene gives phthalic acid

d

The oxidation of α- naphthylamine yields phthalic acid. 

answer is B.

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Detailed Solution

In aromatic compounds, greater the resonance energy more will be the stability of the compound

(A) The resonance stabilization of benzene is 151 kJmol1while of naphthalene is 255 kJmol1.

(B) One ring of naphthalene has lesser resonance stabilization 

(C) Oxidation of 1-nitroaphthalene gives o-nitrophthalic acid. The reason is that the electrons – attracting -NO2 group stabilization the ring to which it is attached towards oxidation thus, it is the other ring gets oxidized. Therefore, the product formed is 3-nitrophthalic acid (o-nitrophthalic acid).

(D) 1-aminonaphthalene (α- naphthylamine) on oxidation gives phthalic acid The electron – releasing - NH2group establishes the ring to which it is attached towards oxidation. Thus, it is the ring which gets oxidized.

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