Which of the following reactions is feasible?

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(B) The reaction in $(A)$ is not feasible because the $C-O$ bond in phenol has partial double bond character due to resonance,making it resistant to n

Vedclass · Accepted Answer

$H_3CCH=CHCH_2OH \xrightarrow{PCC} H_3CCH=CHCHO$

Vedclass · Answer

(B) The reaction in $(A)$ is not feasible because the $C-O$ bond in phenol has partial double bond character due to resonance,making it resistant to nucleophilic substitution by $SOCl_2$.The reaction in $(B)$ is feasible. $PCC$ (Pyridinium chlorochromate) is a selective oxidizing agent that oxidizes primary allylic alcohols to aldehydes without affecting the double bond.The reaction in $(C)$ is not feasible because $KMnO_4/H^{+}$ is a strong oxidizing agent that will oxidize the primary alcohol directly to a carboxylic acid $(CH_3CH_2COOH)$,not an aldehyde.The reaction in $(D)$ is not feasible because $20\%\ H_3PO_4$ is a dilute acid and is not a strong enough dehydrating agent to convert an alcohol to an alkene; concentrated $H_3PO_4$ or $H_2SO_4$ is required.

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