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Question

Bottles containing C6H5I and C6H5CH2I lost their original labels. They were labelled A and B for testing A and B were separately taken in test tubes and boiled with NaOH solution. The end solution in each tube was made acidic with dilute HNO3 and some AgNO3 solution added. Solution B gave a yellow precipitate. Which one of the following statements is true for the experiment?

A
Addition of HNO3 was unnecessary
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B
A was C6H5I
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C
A was C6H5CH2I
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D
B was C6H5I
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Solution

The correct option is B A was C6H5I
Any halides that do not contain electron withdrawing group generally don't react with nucleophiles.
nucleophilic substitution further with HNO3, forming yellow precipitate.

1033151_938160_ans_6a6d42d4914040f5822f0153968fecb3.png

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