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Practical Organic Chemistry question

2020 · 2 Sep · Shift 1 · Q19
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Practical Organic Chemistry question

2020 · 2 Sep · Shift 1 · Q19

JEE MainChemistryPractical Organic ChemistryMCQ+4 / −1
In Carius method of estimation of halogen, 0.172 g of an organic compound showed presence of 0.08 g of bromine. Which of these is the correct structure of the compound?
  1. A
    H3CH_3CH3​C – CH2BrCH_2BrCH2​Br
  2. B
    H3C – Br
  3. C
    JEE Main 2020 (Online) 2nd September Morning Slot Chemistry - Practical Organic Chemistry Question 74 English Option 3
  4. D
    JEE Main 2020 (Online) 2nd September Morning Slot Chemistry - Practical Organic Chemistry Question 74 English Option 4
View written solutionFree

Correct answer: C

  1. Given data
  • Mass of organic compound =0.172 g= 0.172\,\text{g}=0.172g
  • Mass of bromine present =0.08 g= 0.08\,\text{g}=0.08g

We first calculate the percentage of bromine in the compound.

% Br=0.080.172×100\%\,\text{Br} = \frac{0.08}{0.172}\times 100%Br=0.1720.08​×100

% Br≈46.51%\%\,\text{Br} \approx 46.51\%%Br≈46.51%

So, the compound contains about 46.5%46.5\%46.5% bromine by mass.


  1. Check option A: CH3CH2Br\mathrm{CH_3CH_2Br}CH3​CH2​Br (bromoethane)

Molar mass of CH3CH2Br\mathrm{CH_3CH_2Br}CH3​CH2​Br:

M=2(12)+5(1)+80=24+5+80=109M = 2(12) + 5(1) + 80 = 24 + 5 + 80 = 109M=2(12)+5(1)+80=24+5+80=109

Percentage of bromine:

% Br=80109×100≈73.39%\%\,\text{Br} = \frac{80}{109}\times 100 \approx 73.39\%%Br=10980​×100≈73.39%

This does not match 46.5%46.5\%46.5%.

So, Option A is incorrect.


  1. Check option B: CH3Br\mathrm{CH_3Br}CH3​Br (bromomethane)

Molar mass of CH3Br\mathrm{CH_3Br}CH3​Br:

M=12+3+80=95M = 12 + 3 + 80 = 95M=12+3+80=95

Percentage of bromine:

% Br=8095×100≈84.21%\%\,\text{Br} = \frac{80}{95}\times 100 \approx 84.21\%%Br=9580​×100≈84.21%

This also does not match 46.5%46.5\%46.5%.

So, Option B is incorrect.


  1. Find likely molecular mass from bromine percentage

If the compound contains one bromine atom, then

80M×100=46.51\frac{80}{M}\times 100 = 46.51M80​×100=46.51

M=80×10046.51≈172M = \frac{80\times 100}{46.51} \approx 172M=46.5180×100​≈172

So the molar mass of the compound should be about 172172172.

A monobromo compound with molar mass ≈172\approx 172≈172 would be:

C6H5Br\mathrm{C_6H_5Br}C6​H5​Br

since its molar mass is

6(12)+5(1)+80=72+5+80=1576(12) + 5(1) + 80 = 72 + 5 + 80 = 1576(12)+5(1)+80=72+5+80=157

Not enough.

Try dibromo compound with two bromines:

160M×100=46.51\frac{160}{M}\times 100 = 46.51M160​×100=46.51

M≈344M \approx 344M≈344

This is unlikely for the simple options shown.

Now check a compound like C6H5CH2Br\mathrm{C_6H_5CH_2Br}C6​H5​CH2​Br:

M=7(12)+7(1)+80=84+7+80=171M = 7(12) + 7(1) + 80 = 84 + 7 + 80 = 171M=7(12)+7(1)+80=84+7+80=171

Percentage of bromine:

% Br=80171×100≈46.78%\%\,\text{Br} = \frac{80}{171}\times 100 \approx 46.78\%%Br=17180​×100≈46.78%

This matches the observed value very closely.

So the compound is benzyl bromide, C6H5CH2Br\mathrm{C_6H_5CH_2Br}C6​H5​CH2​Br.


  1. Conclusion

The correct structure must be the one corresponding to benzyl bromide.

Hence, the correct option is C.


  1. Comparison with stored correct answer

Stored correct answer: C

My derived answer: C

So, they agree.

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