Question:

Chlorobenzene reacts with trichloroacetaldehyde (chloral) in the presence of \(\mathrm{H_2SO_4}\).
The major product formed is:

Show Hint

This is the industrial synthesis of DDT: electrophilic substitution at the para positions by protonated chloral.
Updated On: Nov 11, 2026
Show Solution
collegedunia
Verified By Collegedunia

The Correct Option is C

Solution and Explanation

Two molecules of chlorobenzene react with one molecule of chloral \(\mathrm{Cl_3C{-}CHO}\) in conc. \(\mathrm{H_2SO_4}\).
Protonated chloral is the electrophile; it attacks the para position of one chlorobenzene (Cl is o,p-directing and para is less hindered), and the resulting alcohol loses water to give a second carbocation that attacks the para position of the second chlorobenzene.
The product is \(p,p'\)-dichlorodiphenyltrichloroethane, \(\mathrm{(p\text{-}ClC_6H_4)_2CH{-}CCl_3}\), i.e. DDT, shown in option (3).
Answer: (3) Cl-C6H4-CH(CCl3)-C6H4-Cl
Was this answer helpful?
0
0