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Hydrocarbons question

2016 · Shift 0 · Q4
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Hydrocarbons question

2016 · Shift 0 · Q4

JEE MainChemistryHydrocarbonsMCQ+4 / −1
The reaction of propene with HOClHOClHOCl (Cl2Cl_2Cl2​ + H2OH_2OH2​O) proceeds through the intermediate:
  1. A
    CH3−CH+−CH2−OH\mathrm{CH}_{3}-\mathrm{CH}^{+}-\mathrm{CH}_{2}-\mathrm{OH}CH3​−CH+−CH2​−OH
  2. B
    CH3−CHCl−CH2+\mathrm{CH}_{3}-\mathrm{CHCl}-\mathrm{CH}_{2}^{+}CH3​−CHCl−CH2+​
  3. C
    CH3CH_3CH3​ - CH+CH^+CH+ - CH2CH_2CH2​ - OHOHOH
  4. D
    CH3−CH+−CH2−Cl\mathrm{CH}_{3}-\mathrm{CH}^{+}-\mathrm{CH}_{2}-\mathrm{Cl}CH3​−CH+−CH2​−Cl
View written solutionFree

Correct answer: D

  1. Identify the reaction type

Propene reacts with HOClHOClHOCl (generated from Cl2+H2OCl_2 + H_2OCl2​+H2​O) to form a halohydrin.

For alkenes, the mechanism is:

  • electrophilic addition of Cl+Cl^+Cl+ to the double bond,
  • formation of a carbocation / bridged chloronium-type intermediate idea,
  • then attack by water.

At the JEE level, this is commonly represented through the more stable carbocation-like intermediate formed after addition of Cl+Cl^+Cl+.


  1. Write the alkene

Propene is:

CH3−CH=CH2CH_3-CH=CH_2CH3​−CH=CH2​

When an electrophile adds, the intermediate should be such that the more stable carbocation is formed.


  1. Apply Markovnikov orientation

If Cl+Cl^+Cl+ adds to the terminal carbon, the positive charge appears on the middle carbon:

CH3−CH+−CH2ClCH_3-CH^+-CH_2ClCH3​−CH+−CH2​Cl

This is a secondary carbocation, which is relatively stable.

If instead the positive charge were on the terminal carbon, we would get a primary carbocation, which is less stable.

So the preferred intermediate is:

CH3−CH+−CH2Cl\mathrm{CH_3-CH^+-CH_2Cl}CH3​−CH+−CH2​Cl
  1. Match with options
  • A: CH3−CH+−CH2OH\mathrm{CH_3-CH^+-CH_2OH}CH3​−CH+−CH2​OH — not the intermediate formed immediately after electrophilic attack.
  • B: CH3−CHCl−CH2+\mathrm{CH_3-CHCl-CH_2^+}CH3​−CHCl−CH2+​ — primary carbocation, less stable.
  • C: same as A in written form.
  • D: CH3−CH+−CH2Cl\mathrm{CH_3-CH^+-CH_2Cl}CH3​−CH+−CH2​Cl — correct.

  1. Final answer

The intermediate is:

CH3−CH+−CH2Cl\boxed{\mathrm{CH_3-CH^+-CH_2Cl}}CH3​−CH+−CH2​Cl​

So the correct option is D.


  1. Comparison with stored answer

Stored correct answer: D

My derived answer: D

They agree.

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