JEE Challenger
More from Haloalkanes and Haloarenes

Estimation of Bromine in Organic Compound using Carius Method

Consider the following reaction.

On estimation of bromine in 1.00 g1.00\text{ g} of R\mathbf{R} using Carius method, the amount of AgBr\text{AgBr} formed (in g\text{g}) is ____________.

[Given: Atomic mass of H=1,C=12,O=16,P=31,Br=80,Ag=108\text{H} = 1, \text{C} = 12, \text{O} = 16, \text{P} = 31, \text{Br} = 80, \text{Ag} = 108]

Question Diagram 1
Official Numerical Answer1.504

Step-by-Step Solution

To determine the amount of AgBr\text{AgBr} formed, we first identify the structure and molecular formula of the major product R\mathbf{R}.

  1. Reaction Step: when 4-bromobenzyl alcohol is treated with red phosphorus and bromine (red phosphorus/Br2\text{red phosphorus}/\text{Br}_2), the primary alcoholic group (−CH2OH-\text{CH}_2\text{OH}) is converted into a bromomethyl group (−CH2Br-\text{CH}_2\text{Br}). The aromatic bromine atom remains unaffected. Br−C6H4−CH2OH→red P/Br2Br−C6H4−CH2Br(R)\text{Br}-\text{C}_6\text{H}_4-\text{CH}_2\text{OH} \xrightarrow{\text{red P}/\text{Br}_2} \text{Br}-\text{C}_6\text{H}_4-\text{CH}_2\text{Br} \quad (\mathbf{R})

  2. Molar Mass of Product R\mathbf{R} (C7H6Br2\text{C}_7\text{H}_6\text{Br}_2): Molar Mass of R=(7×12)+(6×1)+(2×80)=84+6+160=250 g mol−1\text{Molar Mass of } \mathbf{R} = (7 \times 12) + (6 \times 1) + (2 \times 80) = 84 + 6 + 160 = 250\text{ g mol}^{-1}

  3. Moles of R\mathbf{R} in 1.00 g1.00\text{ g}: Moles of R=1.00 g250 g mol−1=0.004 mol\text{Moles of } \mathbf{R} = \frac{1.00\text{ g}}{250\text{ g mol}^{-1}} = 0.004\text{ mol}

  4. Estimation of Bromine using Carius Method: In the Carius method, all bromine atoms present in the organic compound are quantitatively converted into AgBr\text{AgBr}. Since each molecule of R\mathbf{R} contains 22 bromine atoms: Moles of AgBr formed=2×Moles of R=2×0.004 mol=0.008 mol\text{Moles of } \text{AgBr} \text{ formed} = 2 \times \text{Moles of } \mathbf{R} = 2 \times 0.004\text{ mol} = 0.008\text{ mol}

  5. Molar Mass of AgBr\text{AgBr}: Molar Mass of AgBr=108+80=188 g mol−1\text{Molar Mass of } \text{AgBr} = 108 + 80 = 188\text{ g mol}^{-1}

  6. Mass of AgBr\text{AgBr} Formed: Mass of AgBr=0.008 mol×188 g mol−1=1.504 g\text{Mass of } \text{AgBr} = 0.008\text{ mol} \times 188\text{ g mol}^{-1} = 1.504\text{ g}

Rounding to two decimal places, the mass of AgBr\text{AgBr} formed is 1.50 g1.50\text{ g} (or 1.504 g1.504\text{ g}).