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

Question:

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

  1. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCH}_{3}+\mathrm{OI}^{-} / \mathrm{H}_{3} \mathrm{O}^{+}$

  2. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}+\mathrm{KMnO}_{4}$ (Heat), $\mathrm{OH}^{-} / \mathrm{H}_{3} \mathrm{O}^{+}$

  3. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CCl}_{3}+\mathrm{OH}^{-} / \mathrm{H}_{3} \mathrm{O}^{+}$

  4. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}+\mathrm{Mg}, \mathrm{CO}_{2}$ dry ether $/ \mathrm{H}_{3} \mathrm{O}^{+}$


Correct Option: , 4

Solution:

All gives propanoic acid as product but option 4 gives butanoic as product

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