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Haloalkanes and Haloarenes question

2025 · 23 Jan · Shift 1 · Q8
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Haloalkanes and Haloarenes question

2025 · 23 Jan · Shift 1 · Q8

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
Propane molecule on chlorination under photochemical condition gives two di-chloro products, " xxx" and "yyy". Amongst "xxx" and "yyy", "xxx " is an optically active molecule. How many tri-chloro products (consider only structural isomers) will be obtained from " x " when it is further treated with chlorine under the photochemical condition?
  1. A
    4
  2. B
    2
  3. C
    3
  4. D
    5
View written solutionFree

Correct answer: C

  1. Find the two dichloro products of propane

Propane is \ceCH3−CH2−CH3\ce{CH3-CH2-CH3}\ceCH3−CH2−CH3. On chlorination, the possible dichloro structural isomers are:

  • \ce1,1−dichloropropane\ce{1,1-dichloropropane}\ce1,1−dichloropropane: \ceCH3−CH2−CHCl2\ce{CH3-CH2-CHCl2}\ceCH3−CH2−CHCl2
  • \ce1,2−dichloropropane\ce{1,2-dichloropropane}\ce1,2−dichloropropane: \ceCH3−CHCl−CH2Cl\ce{CH3-CHCl-CH2Cl}\ceCH3−CHCl−CH2Cl
  • \ce1,3−dichloropropane\ce{1,3-dichloropropane}\ce1,3−dichloropropane: \ceClCH2−CH2−CH2Cl\ce{ClCH2-CH2-CH2Cl}\ceClCH2−CH2−CH2Cl
  • \ce2,2−dichloropropane\ce{2,2-dichloropropane}\ce2,2−dichloropropane: \ceCH3−CCl2−CH3\ce{CH3-CCl2-CH3}\ceCH3−CCl2−CH3

The question says only two dichloro products, xxx and yyy, are considered, and among them xxx is optically active.

Among these, the only optically active dichloro product is:

\ce1,2−dichloropropane=\ceCH3−CHCl−CH2Cl\ce{1,2-dichloropropane} = \ce{CH3-CHCl-CH2Cl}\ce1,2−dichloropropane=\ceCH3−CHCl−CH2Cl

because the middle carbon is attached to four different groups:

  • \ceH\ce{H}\ceH
  • \ceCl\ce{Cl}\ceCl
  • \ceCH3\ce{CH3}\ceCH3
  • \ceCH2Cl\ce{CH2Cl}\ceCH2Cl

So,

x=\ce1,2−dichloropropanex = \ce{1,2-dichloropropane}x=\ce1,2−dichloropropane


  1. Now chlorinate xxx further to get trichloro products

Starting compound:

\ceCH3−CHCl−CH2Cl\ce{CH3-CHCl-CH2Cl}\ceCH3−CHCl−CH2Cl

We replace one more hydrogen by chlorine under photochemical chlorination.

Count distinct hydrogen-bearing positions:

  • Carbon 1: \ceCH3\ce{CH3}\ceCH3 has 3 H
  • Carbon 2: \ceCHCl\ce{CHCl}\ceCHCl has 1 H
  • Carbon 3: \ceCH2Cl\ce{CH2Cl}\ceCH2Cl has 2 H

Now substitute one H from each distinct carbon position.


  1. Products formed by substitution at each position

(i) Chlorination at carbon 1

\ceCH3−CHCl−CH2Cl−>CH2Cl−CHCl−CH2Cl\ce{CH3-CHCl-CH2Cl -> CH2Cl-CHCl-CH2Cl}\ceCH3−CHCl−CH2Cl−>CH2Cl−CHCl−CH2Cl

This is:

\ce1,2,3−trichloropropane\ce{1,2,3-trichloropropane}\ce1,2,3−trichloropropane


(ii) Chlorination at carbon 2

\ceCH3−CHCl−CH2Cl−>CH3−CCl2−CH2Cl\ce{CH3-CHCl-CH2Cl -> CH3-CCl2-CH2Cl}\ceCH3−CHCl−CH2Cl−>CH3−CCl2−CH2Cl

This is:

\ce1,2,2−trichloropropane\ce{1,2,2-trichloropropane}\ce1,2,2−trichloropropane


(iii) Chlorination at carbon 3

Replacing one H on \ceCH2Cl\ce{CH2Cl}\ceCH2Cl gives:

\ceCH3−CHCl−CHCl2\ce{CH3-CHCl-CHCl2}\ceCH3−CHCl−CHCl2

This is:

\ce1,1,2−trichloropropane\ce{1,1,2-trichloropropane}\ce1,1,2−trichloropropane


  1. Check for any additional structural isomers from stereochemistry

The question says consider only structural isomers, so enantiomers/diastereomers are not counted separately.

Thus the total number of distinct structural trichloro products obtained from xxx is:

333


  1. Match with options

Option C: 3


  1. Comparison with stored correct answer

Stored correct answer = C

Our derived answer = C

So they agree.

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