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Question 54

Compound 'P' on nitration with dil. $$HNO_3$$ yields two isomers (A) and (B). These isomers can be separated by steam distillations. Isomers (A) and (B) show the intramolecular and intermolecular hydrogen bonding respectively. Compound (P) on reaction with conc. $$HNO_3$$ yields a yellow compound 'C', a strong acid. The number of oxygen atoms is present in compound 'C'


Correct Answer: 7

We need to identify compound P, its nitration products, and find the number of oxygen atoms in compound C.

Identify compound P

The key clues are:

- P on mild nitration (dilute $$HNO_3$$) gives two isomers A and B

- A and B can be separated by steam distillation

- A shows intramolecular hydrogen bonding

- B shows intermolecular hydrogen bonding

This is a classic description of phenol ($$C_6H_5OH$$). When phenol is nitrated with dilute $$HNO_3$$:

- It gives ortho-nitrophenol (A) and para-nitrophenol (B)

- ortho-nitrophenol has intramolecular hydrogen bonding (between -OH and -$$NO_2$$ groups on adjacent carbons), making it steam volatile

- para-nitrophenol has intermolecular hydrogen bonding, making it less volatile

- They can be separated by steam distillation because ortho-isomer is steam volatile while para-isomer is not

Identify compound C

When phenol reacts with concentrated $$HNO_3$$, it gives 2,4,6-trinitrophenol (picric acid).

$$C_6H_2(NO_2)_3OH$$

Picric acid is a yellow compound and is a strong acid, matching the description of compound C.

Count oxygen atoms in picric acid

The molecular formula of picric acid is $$C_6H_3N_3O_7$$:

- 3 nitro groups ($$-NO_2$$): each has 2 oxygen atoms = $$3 \times 2 = 6$$ oxygen atoms

- 1 hydroxyl group ($$-OH$$): 1 oxygen atom

- Total oxygen atoms = 6 + 1 = 7

The correct answer is 7.

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