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  • (a)    Why phenol is more acidic than ethanol? (b)    Write the mechanism of acid dehydration of ethanol to yield ether :         <img alt="2 \mathrm{CH}_{

(a)    Why phenol is more acidic than ethanol?
(b)    Write the mechanism of acid dehydration of ethanol to yield ether :

        2 \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH} \frac{\mathrm{H}^{+}}{413 \mathrm{K}} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{3}

 

 

 

 
 
 
 
 

Answers (1)

(a)    Phenol is non-acidic than ethanol because

  • In phenol, due to resonance oxygen atom of OH bond becomes electron deficient which makes the release of H+ easier
  • Stronger acid has a more stable conjugate base. Phenoxide ion is resonance stabilized but ethanoxide ion is not.

(b)    Mechanism of acid dehydration of ethanol to yield ether

2 \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH} \frac{\mathrm{H}^{+}}{413 \mathrm{K}} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{3}

Step I    Protonation

            CH_3CH_2-\underset{..}{\overset{..}{O}}H + H^+\rightarrow CH_3CH_2-\underset{..}{\overset{+}{O}}H_2

Step II    Nucleophilic sttack of alcohol on protonated alcohol

           

Step III    Deprotonation

            CH_3CH_2-\underset{H}{\underset{|}{\underset{..}{\overset{..}{O}}}}-CH_2CH_3 \xrightarrow {-H^+} CH_3CH_2\underset{..}{\overset{..}{O}}CH_2CH_3

Posted by

Sumit Saini

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