Which one of the following reactions will not yield propionic acid?

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$C H_{3} C H_{2} C C l_{3} + O H^{-} / H_{3} O^{+}$

$C H_{3} C H_{2} C H_{2} B r + M g, C O_{2} d r y e t h e r / H_{3} O^{+}$

$C H_{3} C H_{2} C O C H_{3} + I O^{-} / H_{3} O^{+}$

$C H_{3} C H_{2} C H_{2} O H + K M n O_{4} / H^{+}$

answer is D.

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Detailed Solution

$\begin{array}{l} C H_{3} C H_{2} - c_{\underset{C l}{|}}^{\overset{C l}{|}} - C l + O^{-} H \overset{}{\to} C H_{3} - C H_{2} - c_{\underset{O H}{|}}^{\overset{O H}{|}} - O H \overset{H_{3} O^{+}}{\to} C H_{3} C H_{2} C O O H + H_{2} O \\ u n s t a b l e \end{array}$
Iodoform reaction $C H_{3} - C H_{2} - \overset{\overset{O}{| |}}{C} - C H_{3} + I O^{-} \overset{}{\to} C H I_{3} + C H_{3} C H_{2} C O O^{-} \overset{H_{3} O^{+}}{\to} C H_{3} C H_{2} C O O H$
$C H_{3} C H_{2} C H_{3} \to_{O H^{-} / H_{3} O^{+}}^{K M n o_{4 / H e a t}} C H_{3} C H_{2} C O O H$
$C H_{3} C H_{2} C H_{2} B r + M g - > C H_{3} C H_{2} C H_{2} M g B r \overset{C O_{2}}{\to} C H_{3} C H_{2} C H_{2} C O O M g B r \overset{H_{3} O^{+}}{\to} \underset{B u \tan o i c a c i d}{C H_{3} C H_{2} C H_{2} C O O H}$