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Which of the following will give white ppt. with aq. ${AgNO}_{3}$ ?

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$Ph - Cl$

$Ph - {CH}_{2} - I$

$H_{2} N - {CH}_{2} {CH}_{2} {CH}_{2} {CH}_{2} - Cl$

answer is D.

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Detailed Solution

Compound that releases Cl^- can form white precipitate of AgCl.

White ppt. of AgCl with silver nitrate are produced by $H_{2} N - {CH}_{2} {CH}_{2} {CH}_{2} {CH}_{2} - Cl$ , as a result formation of a carbocation.

$H_{2} N - {CH}_{2} {CH}_{2} {CH}_{2} {CH}_{2} - Cl + {AgNO}_{3} \to H_{2} N - {CH}_{2} {CH}_{2} {CH}_{2} \overset{+}{{CH}_{2}} + AgCl ↓$

The above carbocation can further rearrange to form a stable carbocation.

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