You have been given four bottles marked $A, B, C$ and $D$ each containing one of the organic compounds given below:
$I: C_6H_5CH_2NH_2$$II: C_6H_5CH_2COOH$
$III: C_6H_5CH_2CH_3$$IV: C_6H_5CH_2CH(NH_2)COOH$

The following observations were made:
$(i)$ The compound in bottle $A$ did not dissolve in either $1 \ N \ NaOH$ or $1 \ N \ HCl$.
$(ii)$ The compound in bottle $B$ dissolved in $1 \ N \ NaOH$ but not in $1 \ N \ HCl$.
$(iii)$ The compound in bottle $C$ dissolved in both $1 \ N \ NaOH$ and $1 \ N \ HCl$.
$(iv)$ The compound in bottle $D$ did not dissolve in $1 \ N \ NaOH$ but dissolved in $1 \ N \ HCl$.
$(a)$ Indicate the compounds in: bottle $A = \dots$,bottle $B = \dots$,bottle $C = \dots$ and bottle $D = \dots$.
$(b)$ The compound with the highest solubility in distilled water is .......

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(D) The solubility of organic compounds in $1 \ N \ NaOH$ (a base) and $1 \ N \ HCl$ (an acid) depends on their acidic or basic nature.
$(i)$ Compound $A$ is neutral as it does not react with either acid or base. Thus,$A = III$ $(C_6H_5CH_2CH_3)$.
$(ii)$ Compound $B$ is acidic as it dissolves in $NaOH$ but not $HCl$. Thus,$B = II$ $(C_6H_5CH_2COOH)$.
$(iii)$ Compound $C$ is amphoteric as it dissolves in both $NaOH$ and $HCl$. Thus,$C = IV$ $(C_6H_5CH_2CH(NH_2)COOH)$.
$(iv)$ Compound $D$ is basic as it dissolves in $HCl$ but not $NaOH$. Thus,$D = I$ $(C_6H_5CH_2NH_2)$.
$(b)$ The compound with the highest solubility in distilled water is $IV$ $(C_6H_5CH_2CH(NH_2)COOH)$ because it exists as a zwitterion $(C_6H_5CH_2CH(NH_3^+)COO^-)$ in water,which is highly polar.

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Consider the following reaction sequence starting from $p$-nitrotoluene:
$(i)$ $\text{Sn/HCl; OH}^-$
(ii) $(\text{CH}_3\text{CO})_2\text{O}$
(iii) $\text{Br}_2/\text{AlBr}_3$
(iv) $\text{H}_3\text{O}^+$
When the final product $(P)$ is subjected to Carius analysis using $\text{AgNO}_3$, $1.0 \text{ g}$ of the product $(P)$ will produce . . . . . . $\text{g}$ of the precipitate of $\text{AgBr}$. (Nearest Integer)
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