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Haloalkanes and Haloarenes question

2004 · Shift 0 · Q14
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Haloalkanes and Haloarenes question

2004 · Shift 0 · Q14

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
The compound formed on heating chlorobenzene with chloral in the presence concentrated sulphuric acid is
  1. A
    gammexene
  2. B
    hexachloroethane
  3. C
    Freon
  4. D
    DDT
View written solutionFree

Correct answer: D

  1. Identify the reaction

    Chlorobenzene reacts with chloral in the presence of concentrated sulphuric acid to form DDT.

    Chloral is trichloroacetaldehyde, with formula: CCl3CHO\mathrm{CCl_3CHO}CCl3​CHO

  2. Write the reaction

    Two molecules of chlorobenzene condense with one molecule of chloral in acidic medium: 2 C6H5Cl+CCl3CHO→conc. H2SO4(pext−ClC6H4)2CHCCl3+H2O2\,\mathrm{C_6H_5Cl} + \mathrm{CCl_3CHO} \xrightarrow[\text{conc. }H_2SO_4]{} \mathrm{(p ext{-}ClC_6H_4)_2CHCCl_3} + H_2O2C6​H5​Cl+CCl3​CHOconc. H2​SO4​​(pext−ClC6​H4​)2​CHCCl3​+H2​O

    The product is DDT, whose full name is: 1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane\text{1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane}1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane

  3. Check the options

    • A: gammexene — This is benzene hexachloride (BHC), formed by addition of chlorine to benzene in sunlight, not by this reaction.
    • B: hexachloroethane — Not formed here.
    • C: Freon — Chlorofluorocarbon compounds, unrelated to this reaction.
    • D: DDT — Correct.

  4. Conclusion

    The compound formed is: DDT\boxed{\text{DDT}}DDT​

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