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Question

Consider the following reactions sequence

When the product (P) is subjected to Carius analysis using $\text{AgNO}_3$, $1.0\text{ g}$ of the product (P) will produce __________ g of the precipitate of AgBr. (Nearest Integer)
(Given : molar mass in $\text{g mol}^{-1}$ C : 12, H : 1, O : 16, N : 14, Br : 80, Ag : 108)

Step 1: Identify the starting compound
The given compound is p-nitrotoluene (–CH₃ and –NO₂ in para position).

Step 2: Apply the reaction sequence

(i) Sn/HCl, OH⁻ → Reduction
$-NO_2 \rightarrow -NH_2$
Product: p-toluidine

(ii) $(CH_3CO)_2O$ → Acetylation
$-NH_2 \rightarrow -NHCOCH_3$ (protection)
Product: p-methyl acetanilide

(iii) Br₂ / AlBr₃ → Bromination

  • $-NHCOCH_3$ is ortho/para directing
  • Para position already occupied by $-CH_3$
    → Bromination occurs at ortho position

Product: o-bromo p-methyl acetanilide

(iv) $H_3O^+$ → Hydrolysis
Removes acetyl group
→ Final product (P): o-bromo p-toluidine

Step 3: Number of Br atoms in product
Each molecule of P contains 1 Br atom

Step 4: Molar mass calculation

For $C_7H_8BrN$:

  • C: $7 \times 12 = 84$
  • H: $8 \times 1 = 8$
  • N: $14$
  • Br: $80$

Total molar mass = 186 g/mol

Step 5: AgBr formed (Carius method)

1 mole Br → 1 mole AgBr

Molar mass of AgBr = $108 + 80 = 188$

Step 6: Final calculation

From 1 g of P:

$AgBr=188186≈1.01 g\text{AgBr} = \frac{188}{186} \approx 1.01 \, \text{g}    AgBr=186188​≈1.01g $

 

Final Answer (Nearest Integer):
1 g

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Similar Questions

  1. In Dumas method for estimation of nitrogen, 0.50 g of an organic compound gave 70 mL of nitrogen collected at 300 K and 715 mm pressure. The percentage of nitrogen in the organic compound is ______ %.
    (Aqueous tension at 300 K is 15 mm).
  2. $0.25 \text{ g}$ of an organic compound "A" containing carbon, hydrogen and oxygen was analysed using the combustion method. There was an increase in mass of $\text{CaCl}_2$ tube and potash tube at the end of the experiment. The amount was found to be $0.15 \text{ g}$ and $0.1837 \text{ g}$, respectively. The percentage of oxygen in compound A is ______ %. (Nearest integer)
    (Given: molar mass in $\text{g mol}^{-1}$ $\text{H} : 1, \text{C} : 12, \text{O} : 16$)
  3. Grignard reagent $\text{RMgBr (P)}$ reacts with water and forms a gas $\text{(Q)}$. One gram of Q occupies $1.4 \text{ dm}^3$ at STP. (P) on reaction with dry ice in dry ether followed by $\text{H}_3\text{O}^+$ forms a compound $\text{(Z)}$. 0.1 mole of $\text{(Z)}$ will weigh _________ g. (Nearest integer)
  4. Consider all the structural isomers with molecular formula $\text{C}_5\text{H}_{11}\text{Br}$ are separately treated with $\text{KOH(aq)}$ to give respective substitution products, without any rearrangement. The number of products which can exhibit optical isomerism from these is ___________.
  5. Consider the following sequence of reactions to give the major product (X)

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Important Questions from Organic Chemistry

  1. In Dumas method for estimation of nitrogen, 0.50 g of an organic compound gave 70 mL of nitrogen collected at 300 K and 715 mm pressure. The percentage of nitrogen in the organic compound is ______ %.
    (Aqueous tension at 300 K is 15 mm).
  2. $0.25 \text{ g}$ of an organic compound "A" containing carbon, hydrogen and oxygen was analysed using the combustion method. There was an increase in mass of $\text{CaCl}_2$ tube and potash tube at the end of the experiment. The amount was found to be $0.15 \text{ g}$ and $0.1837 \text{ g}$, respectively. The percentage of oxygen in compound A is ______ %. (Nearest integer)
    (Given: molar mass in $\text{g mol}^{-1}$ $\text{H} : 1, \text{C} : 12, \text{O} : 16$)
  3. Grignard reagent $\text{RMgBr (P)}$ reacts with water and forms a gas $\text{(Q)}$. One gram of Q occupies $1.4 \text{ dm}^3$ at STP. (P) on reaction with dry ice in dry ether followed by $\text{H}_3\text{O}^+$ forms a compound $\text{(Z)}$. 0.1 mole of $\text{(Z)}$ will weigh _________ g. (Nearest integer)
  4. Consider all the structural isomers with molecular formula $\text{C}_5\text{H}_{11}\text{Br}$ are separately treated with $\text{KOH(aq)}$ to give respective substitution products, without any rearrangement. The number of products which can exhibit optical isomerism from these is ___________.
  5. The major products U and V in the following reaction are

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