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Hydrocarbons question

2002 · Shift 0 · Q18
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Hydrocarbons question

2002 · Shift 0 · Q18

JEE MainChemistryHydrocarbonsMCQ+4 / −1
What is the product when acetylene reacts with hypochlorous acid ?
  1. A
    CH3COCICH_3COCICH3​COCI
  2. B
    ClCH2CHOClCH_2CHOClCH2​CHO
  3. C
    Cl2CHCHOCl_2CHCHOCl2​CHCHO
  4. D
    ClCHCOOH
View written solutionFree

Correct answer: B

  1. Identify the reaction type

Acetylene is ethyne, HC≡CHHC\equiv CHHC≡CH.

Hypochlorous acid is HOClHOClHOCl, which adds across a multiple bond. For alkynes, addition of HOClHOClHOCl gives a vinyl halohydrin, which then undergoes keto-enol tautomerism to form a carbonyl compound.


  1. Addition of HOClHOClHOCl to acetylene

Across the triple bond of acetylene:

HC≡CH+HOCl→CHCl=CHOHHC\equiv CH + HOCl \rightarrow CHCl=CHOHHC≡CH+HOCl→CHCl=CHOH

This is the enol form.


  1. Tautomerism of the enol

The enol CHCl=CHOHCHCl=CHOHCHCl=CHOH tautomerizes to the corresponding aldehyde:

CHCl=CHOH⇌ClCH2CHOCHCl=CHOH \rightleftharpoons ClCH_2CHOCHCl=CHOH⇌ClCH2​CHO

So the product is chloroacetaldehyde.


  1. Match with options
  • A: CH3COClCH_3COClCH3​COCl = acetyl chloride, not formed here
  • B: ClCH2CHOClCH_2CHOClCH2​CHO = chloroacetaldehyde, correct
  • C: Cl2CHCHOCl_2CHCHOCl2​CHCHO = dichloroacetaldehyde, would require two Cl atoms
  • D: ClCHCOOHClCHCOOHClCHCOOH = not the product of this addition

  1. Conclusion

The product formed when acetylene reacts with hypochlorous acid is:

ClCH2CHO\boxed{ClCH_2CHO}ClCH2​CHO​

So the correct option is B.

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