Q38 / 160 · TS EAMCET 2023 (13 May Shift 2) · Chemistry

Which of the following reaction is feasible?

  • A
    Figure
  • Correct answer
    B
    $\mathrm{H}_3 \mathrm{CCH}=\mathrm{CHCH}_2 \mathrm{OH} \stackrel{\mathrm{PCC}}{\longrightarrow} \mathrm{H}_3 \mathrm{CCH}=\mathrm{CHCHO}$
  • C
    $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{OH} \stackrel{\mathrm{KMnO}_4}{\mathrm{H}^{+}} \mathrm{H}_3 \mathrm{CCH}_2 \mathrm{CHO}$
  • D
    Figure

Solution

Reaction in (a) is not feasible because replacement of $-\mathrm{OH}$ by $-\mathrm{Cl}$ is not possible for phenol due to partial $\mathrm{C}$ $=\mathrm{O}$ bond and resonance stabilization. Reaction is (c) is not feasible because $\mathrm{KMnO}_4$ is a strong oxidizing agent and converts $-\mathrm{C}-\mathrm{OH}$ to $-\mathrm{COOH}$. Reaction in (d) is not feasible because $20 \% \mathrm{PO}_4$ is not a strong enough dehydrating agent and therefore $85 \% \mathrm{~h}_3$ $\mathrm{PO}_4$ is used.

Hence, the correct answer is option: 'B'.

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