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Q. Predict the correct intermediate and product in the following reaction
$H_{3}C-C\equiv CH\overset{H_{2} O , H_{2} S O_{4}}{ \rightarrow }\underset{\left(\right. X \left.\right)}{i n t e r m e d i a t e} \rightarrow \underset{\left(\right. Y \left.\right)}{p r o d u c t}$

NTA AbhyasNTA Abhyas 2022

Solution:

Here first addition reaction occurs according to Markonikov reaction than tautomerisation occurs to give acetone as follows
$\left(\text{H}\right)_{3} \text{C} - \text{C} \equiv \text{CH} \overset{\left(\text{H}\right)_{2} \text{O}}{ \rightarrow } \left(\text{CH}\right)_{3} \underset{\text{OH}}{\underset{\left|\right.}{- \text{C} =}} \left(\text{CH}\right)_{2} \overset{\text{Tautomerisation}}{ \rightarrow } \left(\text{CH}\right)_{3} - \overset{\text{O}}{\overset{\left|\right. \left|\right.}{\text{C}}} - \left(\text{CH}\right)_{3} \left(\text{Y}\right)$