JEE PYQ: Haloalkanes And Haloarenes Question 12
Question 12 - 2019 (08 Apr Shift 2)
The major product of the following reaction is:
$p$-Chlorotoluene $\xrightarrow{(1)\ \text{Cl}_2/h\nu}$ $\xrightarrow{(2)\ \text{H}_2\text{O},\ \Delta}$
(1) $p$-Chlorobenzaldehyde (CHO with Cl)
(2) $p$-Chlorobenzoic acid ($\text{CO}_2\text{H}$ with Cl)
(3) $p$-Chlorobenzyl alcohol ($\text{CH}_2\text{OH}$ with Cl)
(4) $p$-Chlorobenzal chloride ($\text{CHCl}_2$ with Cl)
Show Answer
Answer: (1)
Solution
$p$-Chlorotoluene $\xrightarrow{\text{Cl}_2/h\nu}$ $p$-chlorobenzal chloride ($\text{CHCl}_2$) $\xrightarrow{\text{H}_2\text{O},\Delta}$ $p$-chlorobenzaldehyde (via unstable gem-diol intermediate which loses water to give CHO).