Question

An organic compound $C{H}_{3}CH\left(OH\right)C{H}_3$ on treatment with acidified $K_{2}C{r}_2{O}_7$ gives a compound $Y$, which reacts with $I_2$ and sodium carbonate to form triiodomethane. The compound $Y$ is

• A. $C{H}_{3}OH$
• B. $C{H}_{3}COC{H}_3$
• C. $C{H}_{3}CHO$
• D. $C{H}_{3}CH\left(OH\right)C{H}_3$

Answer 1

Answer: (B)

$C{H}_{3}COC{H}_3$

$2^o$ alcohols give ketones with acidified $K_{2}C{r}_2{O}_7$. Ketones containing $C{H}_{3}CO-$ type perform haloform.
Here, $Y$ is formed by the oxidation of propan-2-ol. So, it must be acetone.
The reaction is given below:
$C{H}_{3}CH\left(OH\right)C{H}_3\stackrel{K_{2}C{r}_2{O}_7}{\to }C{H}_{3}COC{H}_3\stackrel{I_2}{\to }CH{I}_3$