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Haloalkanes and Haloarenes question

2021 · 26 Aug · Shift 2 · Q22
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Haloalkanes and Haloarenes question

2021 · 26 Aug · Shift 2 · Q22

JEE MainChemistryHaloalkanes and HaloarenesNumerical+4 / −1
A chloro compound "A". (i) forms aldehydes on ozonolysis followed by the hydrolysis. (ii) when vaporized completely 1.53 g of A, gives 448 mL of vapour at STP. The number of carbon atoms in a molecule of compound A is ‾\underline{\hspace{2cm}}​.
Numerical answer
View written solutionFree

Correct answer: 3

  1. Find molar mass of compound AAA from vapour data

At STP, 111 mole of gas occupies 22.4 L=22400 mL22.4\,\text{L} = 22400\,\text{mL}22.4L=22400mL.

Given volume of vapour: 448 mL=0.448 L448\,\text{mL} = 0.448\,\text{L}448mL=0.448L

So moles of AAA are: n=0.44822.4=0.02 moln = \frac{0.448}{22.4} = 0.02\,\text{mol}n=22.40.448​=0.02mol

Given mass of AAA is 1.53 g1.53\,\text{g}1.53g, hence molar mass: M=1.530.02=76.5 g mol−1M = \frac{1.53}{0.02} = 76.5\,\text{g mol}^{-1}M=0.021.53​=76.5g mol−1


  1. Use the fact that AAA is a chloro compound

Let the molecular formula of a monochloro compound be: CnHmCl\mathrm{C_nH_mCl}Cn​Hm​Cl

Its molar mass is: 12n+m+35.5=76.512n + m + 35.5 = 76.512n+m+35.5=76.5

So, 12n+m=4112n + m = 4112n+m=41

Now test integer values of nnn:

  • If n=1n=1n=1, then m=29m=29m=29 impossible
  • If n=2n=2n=2, then m=17m=17m=17 impossible
  • If n=3n=3n=3, then m=5m=5m=5 possible, giving formula: C3H5Cl\mathrm{C_3H_5Cl}C3​H5​Cl
  • If n=4n=4n=4, then m=−7m=-7m=−7 impossible

Thus the molecular formula is: C3H5Cl\mathrm{C_3H_5Cl}C3​H5​Cl

So the compound has 3 carbon atoms.


  1. Check ozonolysis condition

Degree of unsaturation for C3H5Cl\mathrm{C_3H_5Cl}C3​H5​Cl:

For a saturated acyclic monochloro compound, formula would be CnH2n+1Cl\mathrm{C_nH_{2n+1}Cl}Cn​H2n+1​Cl. For n=3n=3n=3, saturated formula is C3H7Cl\mathrm{C_3H_7Cl}C3​H7​Cl. But actual formula is C3H5Cl\mathrm{C_3H_5Cl}C3​H5​Cl, i.e. it has two fewer H, so it contains one double bond.

Hence AAA is an alkenyl chloride.

A suitable structure is allyl chloride: CH2=CH−CH2Cl\mathrm{CH_2=CH-CH_2Cl}CH2​=CH−CH2​Cl

On ozonolysis of the double bond followed by hydrolysis, it forms aldehyde-containing products (notably formaldehyde), which is consistent with the statement.

Thus the data are self-consistent.


  1. Final answer

The number of carbon atoms in compound AAA is: 3\boxed{3}3​

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